Fix: Resolved an issue where Cron scheduled tasks failed to auto-sync due to an overly short trigger grace period.

Set `misfire_grace_time=60, coalesce=True`

app/config.json

@@ -2,11 +2,27 @@
     "theme": "auto",
     "token": "",
     "server_url": "",
-    "server_port": "32400",
     "server_scheme": "https",
+    "server_port": "32400",
     "timeout": 9,
     "library_name": "",
     "sync_mode": "merge_local_primary",
     "local_path": "playlist",
-    "path_rules": []
-}
+    "path_rules": [],
+    "path_mapping": {
+        "mode": "SIMPLE",
+        "simple": [],
+        "regex": {
+            "local_pre": [],
+            "local_post": [],
+            "remote_pre": [],
+            "remote_post": []
+        }
+    },
+    "schedule_mode": "DISABLED",
+    "schedule_cron": "",
+    "schedule_daily_time": "02:00",
+    "schedule_weekly_days": [0],
+    "schedule_weekly_time": "03:00",
+    "schedule_auto_watch": false
+}

app/main.py

@@ -92,9 +92,29 @@ class RegexRule(BaseModel):
     replacement: str = ""
 
 
+class ReplacementRule(BaseModel):
+    id: str = ""
+    search: str
+    replace: str = ""
+
+
+class RegexRulesGroup(BaseModel):
+    local_pre: list[ReplacementRule] = []
+    local_post: list[ReplacementRule] = []
+    remote_pre: list[ReplacementRule] = []
+    remote_post: list[ReplacementRule] = []
+
+
+class PathMappingPayload(BaseModel):
+    mode: str = "SIMPLE"
+    simple: list[ReplacementRule] = []
+    regex: RegexRulesGroup = RegexRulesGroup()
+
+
 class SyncSettingsResponse(BaseModel):
     sync_mode: str
     path_rules: list[RegexRule]
+    path_mapping: dict | None = None
     local_path: str
     library_name: str | None = None
     server_url: str | None = None
@@ -352,6 +372,7 @@ async def get_settings():
     return SyncSettingsResponse(
         sync_mode=server_config.sync_mode,
         path_rules=rules,
+        path_mapping=server_config.path_mapping,
         local_path=server_config.local_path,
         library_name=server_config.library_name,
         server_url=server_config.url,
@@ -380,6 +401,22 @@ async def update_regex_rules(payload: RegexRulePayload):
     return {"rules": payload.rules}
 
 
+@app.put("/api/settings/path-mapping")
+async def update_path_mapping(payload: PathMappingPayload):
+    path_mapping_dict = {
+        "mode": payload.mode,
+        "simple": [{"id": rule.id, "search": rule.search, "replace": rule.replace} for rule in payload.simple],
+        "regex": {
+            "local_pre": [{"id": rule.id, "search": rule.search, "replace": rule.replace} for rule in payload.regex.local_pre],
+            "local_post": [{"id": rule.id, "search": rule.search, "replace": rule.replace} for rule in payload.regex.local_post],
+            "remote_pre": [{"id": rule.id, "search": rule.search, "replace": rule.replace} for rule in payload.regex.remote_pre],
+            "remote_post": [{"id": rule.id, "search": rule.search, "replace": rule.replace} for rule in payload.regex.remote_post],
+        }
+    }
+    server_config.set_and_save_config(path_mapping=path_mapping_dict)
+    return {"path_mapping": server_config.path_mapping}
+
+
 @app.put("/api/settings/library")
 async def update_library(payload: LibrarySelection):
     server_config.set_and_save_config(library_name=payload.library_name)

app/utils/config.py

@@ -3,6 +3,16 @@ import os
 from app.utils.logger import logger
 
 DEFAULT_SYNC_MODE = "merge_local_primary"
+DEFAULT_PATH_MAPPING = {
+    "mode": "SIMPLE",
+    "simple": [],
+    "regex": {
+        "local_pre": [],
+        "local_post": [],
+        "remote_pre": [],
+        "remote_post": []
+    }
+}
 
 CONFIG_PATH = os.path.abspath(
     os.path.join(os.path.dirname(__file__), "..", "config.json")
@@ -21,7 +31,8 @@ class ServerConfig:
         self.library_name = ""
         self.sync_mode = DEFAULT_SYNC_MODE
         self.local_path = "playlist"
-        self.path_rules: list[dict[str, str]] = []
+        self.path_rules: list[dict[str, str]] = []  # Legacy field for backward compatibility
+        self.path_mapping: dict = DEFAULT_PATH_MAPPING.copy()
         self.schedule_mode = "DISABLED"
         self.schedule_cron = ""
         self.schedule_daily_time = "02:00"
@@ -55,6 +66,23 @@ class ServerConfig:
         self.sync_mode = config.get("sync_mode", DEFAULT_SYNC_MODE)
         self.local_path = config.get("local_path", "playlist")
         self.path_rules = config.get("path_rules", []) or []
+        
+        # Load path_mapping with default fallback
+        path_mapping_config = config.get("path_mapping")
+        if path_mapping_config:
+            self.path_mapping = {
+                "mode": path_mapping_config.get("mode", "SIMPLE"),
+                "simple": path_mapping_config.get("simple", []),
+                "regex": {
+                    "local_pre": path_mapping_config.get("regex", {}).get("local_pre", []),
+                    "local_post": path_mapping_config.get("regex", {}).get("local_post", []),
+                    "remote_pre": path_mapping_config.get("regex", {}).get("remote_pre", []),
+                    "remote_post": path_mapping_config.get("regex", {}).get("remote_post", [])
+                }
+            }
+        else:
+            self.path_mapping = DEFAULT_PATH_MAPPING.copy()
+        
         self.schedule_mode = config.get("schedule_mode", "DISABLED")
         self.schedule_cron = config.get("schedule_cron", "")
         self.schedule_daily_time = config.get("schedule_daily_time", "02:00")
@@ -76,6 +104,7 @@ class ServerConfig:
             "sync_mode": self.sync_mode,
             "local_path": self.local_path,
             "path_rules": self.path_rules,
+            "path_mapping": self.path_mapping,
             "schedule_mode": self.schedule_mode,
             "schedule_cron": self.schedule_cron,
             "schedule_daily_time": self.schedule_daily_time,
@@ -121,6 +150,21 @@ class ServerConfig:
     def set_path_rules(self, path_rules: list[dict[str, str]]) -> None:
         self.path_rules = path_rules or []
 
+    def set_path_mapping(self, path_mapping: dict) -> None:
+        if path_mapping:
+            self.path_mapping = {
+                "mode": path_mapping.get("mode", "SIMPLE"),
+                "simple": path_mapping.get("simple", []),
+                "regex": {
+                    "local_pre": path_mapping.get("regex", {}).get("local_pre", []),
+                    "local_post": path_mapping.get("regex", {}).get("local_post", []),
+                    "remote_pre": path_mapping.get("regex", {}).get("remote_pre", []),
+                    "remote_post": path_mapping.get("regex", {}).get("remote_post", [])
+                }
+            }
+        else:
+            self.path_mapping = DEFAULT_PATH_MAPPING.copy()
+
     def set_schedule(
         self,
         mode: str,
@@ -150,6 +194,7 @@ class ServerConfig:
         sync_mode: str | None = None,
         local_path: str | None = None,
         path_rules: list[dict[str, str]] | None = None,
+        path_mapping: dict | None = None,
     ) -> None:
         if theme is not None:
             self.set_theme(theme)
@@ -171,6 +216,8 @@ class ServerConfig:
             self.set_local_path(local_path)
         if path_rules is not None:
             self.set_path_rules(path_rules)
+        if path_mapping is not None:
+            self.set_path_mapping(path_mapping)
         self.save()
 
 

app/utils/playlist_merge.py

@@ -40,6 +40,15 @@ class PlaylistSyncResult:
     output_dir: str
 
 
+@dataclass
+class CompiledRegexRules:
+    """Holds compiled regex rules for all four processing stages."""
+    local_pre: list[tuple[re.Pattern[str], str]]
+    local_post: list[tuple[re.Pattern[str], str]]
+    remote_pre: list[tuple[re.Pattern[str], str]]
+    remote_post: list[tuple[re.Pattern[str], str]]
+
+
 def load_paths(text: str) -> list[str]:
     """Normalize playlist text into a list of absolute paths.
 
@@ -72,12 +81,21 @@ def save_paths(paths: Sequence[str]) -> str:
 
 
 def _compile_regex_rules(rules: Sequence[dict[str, str]]) -> list[tuple[re.Pattern[str], str]]:
+    """Compile regex rules into pattern/replacement pairs.
+    
+    Supports both legacy format (pattern/replacement) and new format (search/replace).
+    """
     compiled: list[tuple[re.Pattern[str], str]] = []
     for rule in rules:
-        pattern = rule.get("pattern")
+        # Support both legacy (pattern/replacement) and new (search/replace) field names
+        # Use explicit None checks to allow empty strings as valid values
+        pattern = rule.get("pattern") if rule.get("pattern") is not None else rule.get("search")
         if not pattern:
             continue
-        replacement = rule.get("replacement", "")
+        # For replacement, empty string is a valid value (for deletion)
+        replacement = rule.get("replacement") if rule.get("replacement") is not None else rule.get("replace")
+        if replacement is None:
+            replacement = ""
         try:
             compiled.append((re.compile(pattern), replacement))
         except re.error as exc:
@@ -234,9 +252,31 @@ def _merge_chunks(
     return chunks
 
 
-def _write_results(merged_lines: Sequence[str], folder: str) -> None:
-    _save_playlist_to_folder("local_result.m3u8", merged_lines, folder)
-    _save_playlist_to_folder("remote_result.m3u8", merged_lines, folder)
+def _write_results(
+    merged_lines: Sequence[str], 
+    folder: str,
+    compiled_rules: CompiledRegexRules | None = None
+) -> None:
+    """Write sync results to the test folder.
+    
+    If compiled_rules is provided with post-processing rules:
+    - local_result.m3u8: merged_lines processed with local_post rules
+    - remote_result.m3u8: merged_lines processed with remote_post rules
+    - base_next.m3u8: unprocessed merged_lines (normalized sync result)
+    """
+    # Apply post-processing regex rules if provided
+    if compiled_rules and compiled_rules.local_post:
+        local_lines = _apply_compiled_rules_to_paths(merged_lines, compiled_rules.local_post)
+    else:
+        local_lines = list(merged_lines)
+    
+    if compiled_rules and compiled_rules.remote_post:
+        remote_lines = _apply_compiled_rules_to_paths(merged_lines, compiled_rules.remote_post)
+    else:
+        remote_lines = list(merged_lines)
+    
+    _save_playlist_to_folder("local_result.m3u8", local_lines, folder)
+    _save_playlist_to_folder("remote_result.m3u8", remote_lines, folder)
     _save_playlist_to_folder("base_next.m3u8", merged_lines, folder)
 
 
@@ -379,12 +419,16 @@ def merge_playlists(
     remote_text: str,
     strategy: ConflictResolutionStrategy = ConflictResolutionStrategy.LOCAL_PRIORITY,
     test_folder: str = TEST_PLAYLIST_DIR,
+    compiled_rules: CompiledRegexRules | None = None,
 ) -> MergeResult:
     """Merge playlists using diff3 and resolve conflicts per strategy.
 
     The base, local, and remote normalized playlists are saved into ``test_folder``
     for inspection. The merged playlist is also stored twice to simulate the
     versions intended for local save and cloud upload.
+    
+    If compiled_rules is provided, post-processing regex rules will be applied
+    to the results before writing.
     """
 
     base_paths, local_paths, remote_paths = _normalize_inputs(
@@ -420,7 +464,7 @@ def merge_playlists(
             merged_lines, base_paths, local_paths, remote_paths
         )
 
-    _write_results(merged_lines, test_folder)
+    _write_results(merged_lines, test_folder, compiled_rules)
 
     return MergeResult(merged_paths=merged_lines, conflicts=conflicts)
 
@@ -517,6 +561,7 @@ def _sync_single_playlist(
     remote_text: str,
     playlist_folder: str,
     remote_present: bool,
+    compiled_rules: CompiledRegexRules | None = None,
 ) -> PlaylistSyncResult:
     local_present = local_text is not None
     local_text = local_text or ""
@@ -535,7 +580,7 @@ def _sync_single_playlist(
             base_text, local_text, remote_text, playlist_folder
         )
         merged_lines = list(local_paths)
-        _write_results(merged_lines, playlist_folder)
+        _write_results(merged_lines, playlist_folder, compiled_rules)
         return PlaylistSyncResult(playlist, merged_lines, [], "synced", playlist_folder)
 
     if mode == SyncMode.REMOTE_FORCE:
@@ -547,7 +592,7 @@ def _sync_single_playlist(
             base_text, local_text, remote_text, playlist_folder
         )
         merged_lines = list(remote_paths)
-        _write_results(merged_lines, playlist_folder)
+        _write_results(merged_lines, playlist_folder, compiled_rules)
         return PlaylistSyncResult(playlist, merged_lines, [], "synced", playlist_folder)
 
     if mode not in (SyncMode.MERGE_LOCAL_PRIMARY, SyncMode.MERGE_REMOTE_PRIMARY):
@@ -565,6 +610,7 @@ def _sync_single_playlist(
         remote_text=remote_text,
         strategy=merge_strategy,
         test_folder=playlist_folder,
+        compiled_rules=compiled_rules,
     )
 
     if not merge_result.merged_paths and (not local_present or not remote_present):
@@ -578,13 +624,177 @@ def _sync_single_playlist(
     )
 
 
+def _compile_path_mapping_rules(path_mapping: dict) -> CompiledRegexRules:
+    """Compile regex rules from path_mapping config for all four processing stages."""
+    regex_config = path_mapping.get("regex", {})
+    return CompiledRegexRules(
+        local_pre=_compile_regex_rules(regex_config.get("local_pre", [])),
+        local_post=_compile_regex_rules(regex_config.get("local_post", [])),
+        remote_pre=_compile_regex_rules(regex_config.get("remote_pre", [])),
+        remote_post=_compile_regex_rules(regex_config.get("remote_post", [])),
+    )
+
+
+def _compile_simple_mapping_rules(simple_mappings: list[dict]) -> CompiledRegexRules:
+    """Compile simple mapping pairs into four rule groups using UUID-based mapping_ids.
+    
+    Each simple mapping has:
+    - id: UUID used as the mapping_id (unique identifier to prevent conflicts)
+    - search: Local path prefix
+    - replace: Cloud path prefix
+    
+    This generates four rule sets:
+    - local_pre: Replace local path (search) with mapping_id
+    - remote_pre: Replace cloud path (replace) with mapping_id
+    - local_post: Replace mapping_id with local path (search)
+    - remote_post: Replace mapping_id with cloud path (replace)
+    
+    The mapping_id is wrapped with special markers to prevent conflicts with actual paths.
+    """
+    local_pre_rules: list[dict[str, str]] = []
+    local_post_rules: list[dict[str, str]] = []
+    remote_pre_rules: list[dict[str, str]] = []
+    remote_post_rules: list[dict[str, str]] = []
+    
+    # UUID pattern for validation (accepts standard UUID format with or without hyphens)
+    uuid_pattern = re.compile(r'^[a-fA-F0-9]{8}-?[a-fA-F0-9]{4}-?[a-fA-F0-9]{4}-?[a-fA-F0-9]{4}-?[a-fA-F0-9]{12}$')
+    
+    for mapping in simple_mappings:
+        # Get the mapping values
+        mapping_id = mapping.get("id")
+        local_path = mapping.get("search", "")  # Local path is stored in 'search' field
+        cloud_path = mapping.get("replace", "")  # Cloud path is stored in 'replace' field
+        
+        # Validate mapping_id is a proper UUID to prevent injection attacks
+        if not mapping_id or not isinstance(mapping_id, str):
+            logger.warning(f"Skipping mapping with missing or invalid id: {mapping}")
+            continue
+        
+        if not uuid_pattern.match(mapping_id):
+            logger.warning(f"Skipping mapping with non-UUID id format: {mapping_id}")
+            continue
+        
+        # Paths must be non-empty strings
+        if not local_path or not isinstance(local_path, str):
+            logger.warning(f"Skipping mapping with missing local path: {mapping}")
+            continue
+        
+        if not cloud_path or not isinstance(cloud_path, str):
+            logger.warning(f"Skipping mapping with missing cloud path: {mapping}")
+            continue
+        
+        # Normalize Windows paths: Replace double backslashes with single backslashes
+        # This handles cases where users enter escaped paths like \\Koha9-Main\\Music
+        # when the actual playlist content uses \Koha9-Main\Music
+        original_local = local_path
+        original_cloud = cloud_path
+        local_path = local_path.replace("\\\\", "\\")
+        cloud_path = cloud_path.replace("\\\\", "\\")
+        
+        if local_path != original_local or cloud_path != original_cloud:
+            logger.info(f"Normalized Windows paths:")
+            logger.info(f"  Local: {repr(original_local)} -> {repr(local_path)}")
+            logger.info(f"  Cloud: {repr(original_cloud)} -> {repr(cloud_path)}")
+        
+        # Create a unique placeholder using the validated UUID
+        # Using special markers to prevent conflicts with actual paths
+        placeholder = f"__MAPPING__{mapping_id}__"
+        
+        # Debug logging for path mapping
+        logger.debug(f"Simple mapping pair:")
+        logger.debug(f"  Local path (search): {repr(local_path)}")
+        logger.debug(f"  Cloud path (replace): {repr(cloud_path)}")
+        logger.debug(f"  Placeholder: {placeholder}")
+        
+        # Pre-processing rules (use re.escape to treat paths as literal strings)
+        # local_pre: Replace local path with placeholder
+        local_pattern = re.escape(local_path)
+        logger.debug(f"  Local pre pattern: {repr(local_pattern)}")
+        local_pre_rules.append({
+            "pattern": local_pattern,
+            "replacement": placeholder
+        })
+        
+        # remote_pre: Replace cloud path with placeholder
+        remote_pattern = re.escape(cloud_path)
+        logger.debug(f"  Remote pre pattern: {repr(remote_pattern)}")
+        remote_pre_rules.append({
+            "pattern": remote_pattern,
+            "replacement": placeholder
+        })
+        
+        # Post-processing rules
+        # local_post: Replace placeholder with local path
+        # Note: In regex replacement, backslashes need to be escaped
+        local_post_rules.append({
+            "pattern": re.escape(placeholder),
+            "replacement": local_path.replace("\\", "\\\\")
+        })
+        
+        # remote_post: Replace placeholder with cloud path
+        remote_post_rules.append({
+            "pattern": re.escape(placeholder),
+            "replacement": cloud_path.replace("\\", "\\\\")
+        })
+    
+    logger.info(f"Compiled {len(local_pre_rules)} simple mapping pairs into rules")
+    
+    return CompiledRegexRules(
+        local_pre=_compile_regex_rules(local_pre_rules),
+        local_post=_compile_regex_rules(local_post_rules),
+        remote_pre=_compile_regex_rules(remote_pre_rules),
+        remote_post=_compile_regex_rules(remote_post_rules),
+    )
+
+
 def sync_all_playlists(
     local_dir: str, mode: SyncMode, test_folder: str = TEST_PLAYLIST_DIR
 ) -> list[PlaylistSyncResult]:
-    """Synchronize all playlists that can be matched by name."""
+    """Synchronize all playlists that can be matched by name.
+    
+    Path mapping modes:
+    - SIMPLE: Uses UUID-based mapping_ids to convert between local and cloud paths
+      - local_pre: local_path -> mapping_id
+      - remote_pre: cloud_path -> mapping_id
+      - local_post: mapping_id -> local_path
+      - remote_post: mapping_id -> cloud_path
+    
+    - REGEX: Uses custom regex rules for each processing stage
+      - local_pre, local_post, remote_pre, remote_post rules are applied directly
+    
+    Processing flow:
+    1. local_pre rules are applied to local playlists before sync
+    2. remote_pre rules are applied to remote playlists before sync
+    3. Sync/merge is performed
+    4. local_post rules are applied to results before writing to local_result.m3u8
+    5. remote_post rules are applied to results before writing to remote_result.m3u8
+    """
 
     server_config.load()
-    compiled_rules = _compile_regex_rules(server_config.path_rules)
+    
+    # Get path_mapping configuration
+    path_mapping = server_config.path_mapping
+    mapping_mode = path_mapping.get("mode", "SIMPLE")
+    
+    # Compile rules based on the mode
+    compiled_rules: CompiledRegexRules | None = None
+    legacy_compiled_rules: list[tuple[re.Pattern[str], str]] = []
+    
+    if mapping_mode == "REGEX":
+        compiled_rules = _compile_path_mapping_rules(path_mapping)
+        logger.info("Using REGEX mode for path mapping with 4 rule groups")
+    elif mapping_mode == "SIMPLE":
+        simple_mappings = path_mapping.get("simple", [])
+        if simple_mappings:
+            compiled_rules = _compile_simple_mapping_rules(simple_mappings)
+            logger.info(f"Using SIMPLE mode for path mapping with {len(simple_mappings)} mapping pairs")
+        else:
+            logger.info("SIMPLE mode with no mappings - no path transformations will be applied")
+    else:
+        # Use legacy path_rules for backward compatibility
+        legacy_compiled_rules = _compile_regex_rules(server_config.path_rules)
+        logger.info("Using legacy path_rules for preprocessing")
+    
     _ensure_test_dir(test_folder)
     logger.info(f"Syncing playlists to test folder: {test_folder}")
     local_playlists = _load_local_playlists(local_dir)
@@ -613,16 +823,35 @@ def sync_all_playlists(
             remote_text = snapshot_remote_text
             remote_present = bool(remote_text.strip()) or remote_exists
 
-        base_text = preprocess_playlist_text(
-            base_text, server_config.path_rules, compiled_rules
-        )
-        remote_text = preprocess_playlist_text(
-            remote_text, server_config.path_rules, compiled_rules
-        )
-        if local_text is not None:
-            local_text = preprocess_playlist_text(
-                local_text, server_config.path_rules, compiled_rules
+        if compiled_rules:
+            # Apply pre-processing rules for REGEX or SIMPLE mode
+            # base_text doesn't need pre-processing as it's the normalized state
+            if local_text is not None and compiled_rules.local_pre:
+                logger.debug(f"Applying local_pre rules to playlist: {playlist}")
+                logger.debug(f"  Before preprocessing (first 200 chars): {repr(local_text[:200])}")
+                local_text = preprocess_playlist_text(
+                    local_text, [], compiled_rules.local_pre
+                )
+                logger.debug(f"  After preprocessing (first 200 chars): {repr(local_text[:200])}")
+            if remote_text and compiled_rules.remote_pre:
+                logger.debug(f"Applying remote_pre rules to playlist: {playlist}")
+                logger.debug(f"  Before preprocessing (first 200 chars): {repr(remote_text[:200])}")
+                remote_text = preprocess_playlist_text(
+                    remote_text, [], compiled_rules.remote_pre
+                )
+                logger.debug(f"  After preprocessing (first 200 chars): {repr(remote_text[:200])}")
+        elif legacy_compiled_rules:
+            # Use legacy preprocessing for all texts
+            base_text = preprocess_playlist_text(
+                base_text, server_config.path_rules, legacy_compiled_rules
             )
+            remote_text = preprocess_playlist_text(
+                remote_text, server_config.path_rules, legacy_compiled_rules
+            )
+            if local_text is not None:
+                local_text = preprocess_playlist_text(
+                    local_text, server_config.path_rules, legacy_compiled_rules
+                )
 
         # Treat missing remote text as absent playlist.
         result = _sync_single_playlist(
@@ -633,6 +862,7 @@ def sync_all_playlists(
             remote_text=remote_text,
             playlist_folder=playlist_folder,
             remote_present=remote_present,
+            compiled_rules=compiled_rules,
         )
         results.append(result)
 

app/utils/scheduler.py

@@ -143,7 +143,7 @@ def update_scheduler_job():
         trigger = _create_weekly_trigger(server_config.schedule_weekly_days, server_config.schedule_weekly_time)
 
     if trigger:
-        scheduler.add_job(job_function, trigger)
+        scheduler.add_job(job_function, trigger, misfire_grace_time=60, coalesce=True)
         logger.info(f"Added scheduled job with mode '{mode}' and trigger: {trigger}")
     else:
         logger.warning(f"Failed to create trigger for mode '{mode}'. No job added.")

frontend/App.tsx

@@ -1,8 +1,7 @@
-
 import React, { useEffect, useState, useCallback, useRef } from 'react';
-import { Playlist, ServerType, SyncStrategy, PlexServerConnection, RegexReplacement, PlexConnectionSettings, SyncState, ScheduleSettings, ScheduleMode } from './types';
+import { Playlist, ServerType, SyncStrategy, PlexServerConnection, PathMappingConfig, PathMappingMode, PlexConnectionSettings, SyncState, ScheduleSettings, ScheduleMode } from './types';
 import { apiService } from './services/api';
-import {
+import { 
   STRIPE_BASE_SPEED,
   STRIPE_DECEL_DURATION_MS,
   STRIPE_TILE_SIZE,
@@ -10,15 +9,13 @@ import {
   SYNC_SUCCESS_TOTAL_MS,
   SYNC_ERROR_RESET_MS,
   TOAST_AUTO_DISMISS_MS,
-  TOAST_EXIT_DURATION_MS,
-  SYNC_BANNER_PADDING_X,
-  SYNC_BANNER_PADDING_Y,
-  SYNC_BANNER_MIN_WIDTH,
+  TOAST_EXIT_DURATION_MS
 } from './Config';
+import { SYNC_BANNER_PADDING_X, SYNC_BANNER_PADDING_Y, SYNC_BANNER_MIN_WIDTH } from './Config';
 import ServerPanel from './components/ServerPanel';
 import StrategySelector from './components/StrategySelector';
 import ConnectionModal from './components/ConnectionModal';
-import { ArrowLeftRight, ShieldCheck, X, Server, ServerOff, Clock, Eye, EyeOff } from 'lucide-react';
+import { ArrowLeftRight, ShieldCheck, X, Server, ServerOff, Clock, Eye, EyeOff, Type, Code2 } from 'lucide-react';
 
 interface Toast {
   id: number;
@@ -141,8 +138,17 @@ const App: React.FC = () => {
   // Strategy State
   const [currentStrategy, setCurrentStrategy] = useState<SyncStrategy>(SyncStrategy.LOCAL_OVERWRITE);
   
-  // Regex State
-  const [regexReplacements, setRegexReplacements] = useState<RegexReplacement[]>([]);
+  // Path Mapping State (Includes Simple and Regex Rules)
+  const [pathMappingConfig, setPathMappingConfig] = useState<PathMappingConfig>({
+    mode: PathMappingMode.SIMPLE,
+    simple: [],
+    regex: {
+      localPre: [],
+      localPost: [],
+      remotePre: [],
+      remotePost: []
+    }
+  });
 
   // Schedule State
   const [scheduleSettings, setScheduleSettings] = useState<ScheduleSettings>({
@@ -226,7 +232,7 @@ const App: React.FC = () => {
     const result = await apiService.getSettings();
     if (result.status === 'success') {
       setCurrentStrategy(result.data.strategy);
-      setRegexReplacements(result.data.regex);
+      setPathMappingConfig(result.data.pathMapping);
       setLocalPath(result.data.localPath || 'playlist');
       setConnectionSettings(result.data.connection);
     }
@@ -347,14 +353,14 @@ const App: React.FC = () => {
     }
   };
 
-  // Handle Regex Save
-  const handleSaveRegex = async (replacements: RegexReplacement[]) => {
-    setRegexReplacements(replacements);
-    const result = await apiService.saveRegexRules(replacements);
+  // Handle Path Mapping Save
+  const handleSavePathMapping = async (config: PathMappingConfig) => {
+    setPathMappingConfig(config);
+    const result = await apiService.savePathMapping(config);
     if (result.status === 'success') {
-      addToast('Regex preprocessing rules have been saved.');
+      addToast('Path mapping rules have been saved.');
     } else {
-      addToast(result.message || 'Failed to save regex rules.');
+      addToast(result.message || 'Failed to save path mapping rules.');
     }
   };
 
@@ -365,7 +371,7 @@ const App: React.FC = () => {
     setSyncState(SyncState.SYNCING);
     manualSyncInProgress.current = true;
 
-    const result = await apiService.syncPlaylists(currentStrategy, regexReplacements, localPath || undefined);
+    const result = await apiService.syncPlaylists(currentStrategy, pathMappingConfig, localPath || undefined);
 
     manualSyncInProgress.current = false;
 
@@ -513,6 +519,44 @@ const App: React.FC = () => {
 
   const scheduleInfo = getScheduleDisplayInfo();
 
+  // Helper: Calculate Path Mapping Info
+  const getPathMappingDisplayInfo = (config: PathMappingConfig) => {
+    let count = 0;
+    let modeLabel = '';
+    let Icon = Type;
+
+    if (config.mode === PathMappingMode.SIMPLE) {
+        modeLabel = 'Simple';
+        count = config.simple.length;
+        Icon = Type;
+    } else {
+        modeLabel = 'Regex';
+        count = config.regex.localPre.length +
+                config.regex.localPost.length + 
+                config.regex.remotePre.length + 
+                config.regex.remotePost.length;
+        Icon = Code2;
+    }
+
+    if (count === 0) {
+        return {
+            label: 'Path Mapping',
+            value: 'Not Set',
+            active: false,
+            Icon: Icon
+        };
+    }
+
+    return {
+        label: 'Path Mapping',
+        value: `${modeLabel} (${count})`,
+        active: true,
+        Icon: Icon
+    };
+  };
+
+  const pathMappingInfo = getPathMappingDisplayInfo(pathMappingConfig);
+
   return (
     <div className="min-h-screen flex flex-col bg-gray-900 text-gray-100 font-sans overflow-hidden bg-[radial-gradient(ellipse_at_top,_var(--tw-gradient-stops))] from-gray-800 via-gray-900 to-black">
       
@@ -574,7 +618,7 @@ const App: React.FC = () => {
 
           {syncState === SyncState.IDLE ? (
             <>
-              {/* Normal Toolbar */}
+              {/* Normal Toolbar Left */}
               <div className="flex items-center space-x-3">
                 <div className="p-1.5 rounded-lg shadow-lg bg-gradient-to-br from-plex-orange to-yellow-600 text-gray-900 shadow-plex-orange/20">
                    <ArrowLeftRight size={24} strokeWidth={2.5} />
@@ -583,9 +627,20 @@ const App: React.FC = () => {
                   Plex<span className="text-plex-orange">Sync</span>
                 </h1>
               </div>
-
+              
               {/* Normal Toolbar Right */}
               <div className="flex items-center gap-4">
+                  {/* Path Mapping Info */}
+                  <div className="flex flex-col items-end hidden md:flex border-r border-gray-700/50 pr-4 mr-1">
+                     <span className="text-[10px] uppercase font-bold text-gray-500 tracking-wider">
+                       {pathMappingInfo.label}
+                     </span>
+                     <div className={`text-xs font-mono flex items-center gap-1.5 ${pathMappingInfo.active ? 'text-plex-orange' : 'text-gray-600'}`}>
+                        {pathMappingInfo.active && <pathMappingInfo.Icon size={12} />}
+                        <span>{pathMappingInfo.value}</span>
+                     </div>
+                  </div>
+
                   {/* Schedule Info */}
                   <div className="flex flex-col items-end mr-2 md:mr-0 hidden md:flex">
                      <span className="text-[10px] uppercase font-bold text-gray-500 tracking-wider">
@@ -625,6 +680,7 @@ const App: React.FC = () => {
               </div>
             </>
           ) : (
+            /* Syncing / Success Text Banner */
             <div className="absolute inset-0 flex items-center justify-center pointer-events-none z-10">
                <div
                  className="bg-black shadow-none rounded-none border-none"
@@ -691,8 +747,8 @@ const App: React.FC = () => {
               <StrategySelector 
                 currentStrategy={currentStrategy}
                 onSelect={handleStrategyChange}
-                savedRegexReplacements={regexReplacements}
-                onSaveRegex={handleSaveRegex}
+                savedPathMapping={pathMappingConfig}
+                onSavePathMapping={handleSavePathMapping}
                 savedSchedule={scheduleSettings}
                 onSaveSchedule={handleSaveSchedule}
                 syncState={syncState}

frontend/components/ConnectionModal.tsx

@@ -164,8 +164,14 @@ const ConnectionModal: React.FC<ConnectionModalProps> = ({ isOpen, onClose, onCo
   const isConnected = !!connectedServerInfo;
 
   return (
-    <div className="fixed inset-0 z-50 flex items-center justify-center p-4 bg-black/60 backdrop-blur-sm">
-      <div className="bg-gray-900 border border-gray-700 rounded-xl shadow-2xl w-full max-w-md overflow-hidden animate-in fade-in zoom-in duration-200 flex flex-col max-h-[90vh]">
+    <div 
+      className="fixed inset-0 z-50 flex items-center justify-center p-4 bg-black/60 backdrop-blur-sm"
+      onClick={onClose}
+    >
+      <div 
+        className="bg-gray-900 border border-gray-700 rounded-xl shadow-2xl w-full max-w-md overflow-hidden animate-in fade-in zoom-in duration-200 flex flex-col max-h-[90vh]"
+        onClick={(e) => e.stopPropagation()}
+      >
         
         {/* Header */}
         <div className="px-6 py-4 bg-gray-800 border-b border-gray-700 flex items-center justify-between flex-none">

frontend/components/StrategySelector.tsx

@@ -1,5 +1,5 @@
 import React, { useState, useRef, useEffect } from 'react';
-import { SyncStrategy, RegexReplacement, SyncState, ScheduleSettings, ScheduleMode } from '../types';
+import { SyncStrategy, ReplacementRule, PathMappingConfig, PathMappingRules, PathMappingMode, SyncState, ScheduleSettings, ScheduleMode } from '../types';
 import { 
   ArrowRightCircle, 
   ArrowLeftCircle, 
@@ -17,9 +17,25 @@ import {
   Clock,
   Repeat,
   CheckSquare,
-  Square
+  Square,
+  Type,
+  Code2
 } from 'lucide-react';
 
+// Generate a UUID for mapping rules
+const generateUUID = (): string => {
+  // Use crypto.randomUUID() if available (modern browsers)
+  if (typeof crypto !== 'undefined' && typeof crypto.randomUUID === 'function') {
+    return crypto.randomUUID();
+  }
+  // Fallback to manual UUID v4 generation
+  return 'xxxxxxxx-xxxx-4xxx-yxxx-xxxxxxxxxxxx'.replace(/[xy]/g, (c) => {
+    const r = Math.random() * 16 | 0;
+    const v = c === 'x' ? r : (r & 0x3 | 0x8);
+    return v.toString(16);
+  });
+};
+
 interface StrategyOption {
   value: SyncStrategy;
   label: string;
@@ -61,6 +77,29 @@ const STRATEGIES: StrategyOption[] = [
 
 const WEEK_DAYS = ['S', 'M', 'T', 'W', 'T', 'F', 'S'];
 
+// Color Theme Variables for Mapping Editors
+const MAPPING_THEME = {
+  // Container Themes
+  local: {
+    borderColor: "border-blue-500/20",
+    bgColor: "bg-blue-900/10"
+  },
+  remote: {
+    borderColor: "border-green-500/20",
+    bgColor: "bg-green-900/10"
+  },
+  simple: {
+    borderColor: "border-gray-700/50",
+    bgColor: "bg-gray-900/40"
+  },
+  // Input Field Themes
+  inputs: {
+    default: "bg-gray-800 border-gray-700 text-gray-200 focus:border-plex-orange placeholder-gray-600",
+    local: "bg-blue-500/10 border-blue-500/30 text-blue-100 focus:border-blue-400 placeholder-blue-300/30",
+    cloud: "bg-green-500/10 border-green-500/30 text-green-100 focus:border-green-400 placeholder-green-300/30"
+  }
+};
+
 // Helper to determine the actual mode and settings that would be saved based on the current UI state
 const deriveEffectiveSchedule = (schedule: ScheduleSettings, tab: ScheduleMode): ScheduleSettings => {
   const derived = { ...schedule };
@@ -80,11 +119,114 @@ const deriveEffectiveSchedule = (schedule: ScheduleSettings, tab: ScheduleMode):
   return derived;
 };
 
+// Sub-component for a single Mapping Group Editor
+interface MappingGroupEditorProps {
+  title: string;
+  subtitle?: string;
+  rules: ReplacementRule[];
+  onChange: (newRules: ReplacementRule[]) => void;
+  isLocked: boolean;
+  borderColor?: string;
+  bgColor?: string;
+  // Input specific props
+  leftPlaceholder?: string;
+  rightPlaceholder?: string;
+  leftInputClass?: string;
+  rightInputClass?: string;
+}
+
+const MappingGroupEditor: React.FC<MappingGroupEditorProps> = ({ 
+  title, 
+  subtitle, 
+  rules, 
+  onChange, 
+  isLocked,
+  borderColor = "border-gray-700",
+  bgColor = "bg-gray-900/50",
+  leftPlaceholder = "Pattern",
+  rightPlaceholder = "Replace",
+  leftInputClass,
+  rightInputClass
+}) => {
+  
+  const handleAdd = () => {
+    if (isLocked) return;
+    const newId = generateUUID();
+    onChange([...rules, { id: newId, search: '', replace: '' }]);
+  };
+
+  const handleUpdate = (id: string, field: 'search' | 'replace', value: string) => {
+    if (isLocked) return;
+    onChange(rules.map(r => r.id === id ? { ...r, [field]: value } : r));
+  };
+
+  const handleDelete = (id: string) => {
+    if (isLocked) return;
+    onChange(rules.filter(r => r.id !== id));
+  };
+
+  // Default input style if not provided
+  const defaultInputStyle = MAPPING_THEME.inputs.default;
+
+  return (
+    <div className={`p-3 rounded-lg border ${borderColor} ${bgColor} flex flex-col h-full transition-colors`}>
+       <div className="flex items-center justify-between mb-2">
+         <div>
+            <h4 className="text-[10px] font-bold uppercase tracking-wider text-gray-400">{title}</h4>
+            {subtitle && <p className="text-[9px] text-gray-500">{subtitle}</p>}
+         </div>
+         <button 
+           onClick={handleAdd}
+           disabled={isLocked}
+           className="p-1 rounded bg-gray-700/50 hover:bg-gray-600 text-gray-400 hover:text-white transition-colors"
+           title="Add Rule"
+         >
+           <Plus size={12} />
+         </button>
+       </div>
+
+       <div className="flex-1 space-y-2 overflow-y-auto max-h-32 custom-scrollbar pr-1">
+         {rules.length === 0 ? (
+           <div className="text-xs text-gray-600 italic text-center py-2 border border-dashed border-gray-700/50 rounded-lg">
+             No rules defined.
+           </div>
+         ) : (
+           rules.map((rule) => (
+             <div key={rule.id} className="flex items-center space-x-1 animate-in slide-in-from-left-1 duration-200">
+                <input 
+                  type="text" 
+                  placeholder={leftPlaceholder}
+                  value={rule.search}
+                  onChange={(e) => handleUpdate(rule.id, 'search', e.target.value)}
+                  className={`flex-1 min-w-0 border rounded px-1.5 py-1 text-xs focus:outline-none transition-colors ${leftInputClass || defaultInputStyle}`}
+                />
+                <ArrowRightCircle size={10} className="text-gray-600 flex-none opacity-50" />
+                <input 
+                  type="text" 
+                  placeholder={rightPlaceholder}
+                  value={rule.replace}
+                  onChange={(e) => handleUpdate(rule.id, 'replace', e.target.value)}
+                  className={`flex-1 min-w-0 border rounded px-1.5 py-1 text-xs focus:outline-none transition-colors ${rightInputClass || defaultInputStyle}`}
+                />
+                <button 
+                  onClick={() => handleDelete(rule.id)}
+                  className="text-gray-600 hover:text-red-400 p-1 rounded hover:bg-red-500/10 transition-colors flex-none"
+                >
+                  <Trash2 size={12} />
+                </button>
+             </div>
+           ))
+         )}
+       </div>
+    </div>
+  );
+};
+
 interface StrategySelectorProps {
   currentStrategy: SyncStrategy;
   onSelect: (strategy: SyncStrategy, label: string) => void;
-  savedRegexReplacements: RegexReplacement[];
-  onSaveRegex: (replacements: RegexReplacement[]) => void;
+  savedPathMapping: PathMappingConfig;
+  onSavePathMapping: (config: PathMappingConfig) => void;
   savedSchedule: ScheduleSettings;
   onSaveSchedule: (settings: ScheduleSettings) => Promise<boolean>;
   syncState: SyncState;
@@ -94,8 +236,8 @@ interface StrategySelectorProps {
 const StrategySelector: React.FC<StrategySelectorProps> = ({ 
   currentStrategy, 
   onSelect, 
-  savedRegexReplacements, 
-  onSaveRegex,
+  savedPathMapping, 
+  onSavePathMapping,
   savedSchedule,
   onSaveSchedule,
   syncState,
@@ -104,17 +246,16 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
   const [isOpen, setIsOpen] = useState(false);
   const dropdownRef = useRef<HTMLDivElement>(null);
 
-  // Local state for regex editing
-  const [localReplacements, setLocalReplacements] = useState<RegexReplacement[]>([]);
-  const [isRegexDirty, setIsRegexDirty] = useState(false);
+  // Local state for path mapping editing (stores all lists for both modes)
+  const [localPathMapping, setLocalPathMapping] = useState<PathMappingConfig>(savedPathMapping);
+  const [isMappingDirty, setIsMappingDirty] = useState(false);
 
   // Local state for Schedule editing
   const [localSchedule, setLocalSchedule] = useState<ScheduleSettings>(savedSchedule);
   const [isScheduleDirty, setIsScheduleDirty] = useState(false);
   
   // UI State for Schedule Tabs
-  // We initialize active tab based on the saved mode. If DISABLED, default to CRON.
-  const [activeTab, setActiveTab] = useState<ScheduleMode>(
+  const [activeScheduleTab, setActiveScheduleTab] = useState<ScheduleMode>(
     savedSchedule.mode === ScheduleMode.DISABLED ? ScheduleMode.CRON : savedSchedule.mode
   );
 
@@ -123,32 +264,30 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
 
   // Initialize local state when prop updates
   useEffect(() => {
-    setLocalReplacements(JSON.parse(JSON.stringify(savedRegexReplacements)));
-    setIsRegexDirty(false);
-  }, [savedRegexReplacements]);
+    setLocalPathMapping(JSON.parse(JSON.stringify(savedPathMapping)));
+    setIsMappingDirty(false);
+  }, [savedPathMapping]);
 
   useEffect(() => {
     setLocalSchedule(JSON.parse(JSON.stringify(savedSchedule)));
-    // If the saved mode is not disabled, ensure we show that tab.
     if (savedSchedule.mode !== ScheduleMode.DISABLED) {
-      setActiveTab(savedSchedule.mode);
+      setActiveScheduleTab(savedSchedule.mode);
     }
     setIsScheduleDirty(false);
   }, [savedSchedule]);
 
-  // Check dirty state whenever local changes
+  // Check dirty state whenever local mapping changes
   useEffect(() => {
-    const isDifferent = JSON.stringify(localReplacements) !== JSON.stringify(savedRegexReplacements);
-    setIsRegexDirty(isDifferent);
-  }, [localReplacements, savedRegexReplacements]);
+    const isDifferent = JSON.stringify(localPathMapping) !== JSON.stringify(savedPathMapping);
+    setIsMappingDirty(isDifferent);
+  }, [localPathMapping, savedPathMapping]);
 
   // Check dirty state for Schedule (including Active Tab changes)
   useEffect(() => {
-    // We calculate what the "effective" schedule would be if we saved right now.
-    const effectiveLocal = deriveEffectiveSchedule(localSchedule, activeTab);
+    const effectiveLocal = deriveEffectiveSchedule(localSchedule, activeScheduleTab);
     const isDifferent = JSON.stringify(effectiveLocal) !== JSON.stringify(savedSchedule);
     setIsScheduleDirty(isDifferent);
-  }, [localSchedule, savedSchedule, activeTab]);
+  }, [localSchedule, savedSchedule, activeScheduleTab]);
 
   const selectedOption = STRATEGIES.find(s => s.value === currentStrategy) || STRATEGIES[0];
 
@@ -162,47 +301,70 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
     return () => document.removeEventListener('mousedown', handleClickOutside);
   }, []);
 
-  // Determine if tabs have changed from the saved state
-  const initialTab = savedSchedule.mode === ScheduleMode.DISABLED ? ScheduleMode.CRON : savedSchedule.mode;
-  const hasTabChanged = activeTab !== initialTab;
-  const isScheduleActionable = isScheduleDirty || hasTabChanged;
+  const isScheduleActionable = isScheduleDirty || (activeScheduleTab !== (savedSchedule.mode === ScheduleMode.DISABLED ? ScheduleMode.CRON : savedSchedule.mode));
 
   const handleSelect = (strategy: StrategyOption) => {
     if (isLocked) return;
     onSelect(strategy.value, strategy.label);
   };
 
-  // --- Regex Handlers ---
-  const handleAddRegex = () => {
+  // --- Path Mapping Handlers ---
+  const currentMappingMode = localPathMapping.mode;
+  
+  const updateRegexGroup = (section: keyof PathMappingRules, newRules: ReplacementRule[]) => {
     if (isLocked) return;
-    const newId = Date.now().toString();
-    setLocalReplacements(prev => [...prev, { id: newId, pattern: '', replacement: '' }]);
+    setLocalPathMapping(prev => ({
+      ...prev,
+      regex: {
+        ...prev.regex,
+        [section]: newRules
+      }
+    }));
   };
 
-  const handleDeleteRegex = (id: string) => {
+  const updateSimpleGroup = (newRules: ReplacementRule[]) => {
     if (isLocked) return;
-    setLocalReplacements(prev => prev.filter(r => r.id !== id));
+    setLocalPathMapping(prev => ({
+      ...prev,
+      simple: newRules
+    }));
   };
 
-  const handleUpdateRegex = (id: string, field: 'pattern' | 'replacement', value: string) => {
+  const setMappingMode = (mode: PathMappingMode) => {
     if (isLocked) return;
-    setLocalReplacements(prev => prev.map(r => 
-      r.id === id ? { ...r, [field]: value } : r
-    ));
+    setLocalPathMapping(prev => ({ ...prev, mode }));
   };
 
-  const handleResetRegex = () => {
+  const handleResetMapping = () => {
     if (isLocked) return;
-    setLocalReplacements(JSON.parse(JSON.stringify(savedRegexReplacements)));
+    setLocalPathMapping(JSON.parse(JSON.stringify(savedPathMapping)));
   };
 
-  const handleSaveRegex = () => {
+  const handleSaveMappingClick = () => {
     if (isLocked) return;
-    const validReplacements = localReplacements.filter(r => r.pattern.trim() !== '');
-    setLocalReplacements(validReplacements);
-    onSaveRegex(validReplacements);
+    const clean = (rules: ReplacementRule[]) => rules.filter(r => r.search.trim() !== '');
+    
+    // Clean regex rules
+    const cleanRegex = (rules: PathMappingRules): PathMappingRules => ({
+      localPre: clean(rules.localPre),
+      localPost: clean(rules.localPost),
+      remotePre: clean(rules.remotePre),
+      remotePost: clean(rules.remotePost),
+    });
+
+    const cleanedConfig: PathMappingConfig = {
+      mode: localPathMapping.mode,
+      simple: clean(localPathMapping.simple),
+      regex: cleanRegex(localPathMapping.regex),
+    };
+
+    setLocalPathMapping(cleanedConfig);
+    onSavePathMapping(cleanedConfig);
   };
 
+  const regexRules = localPathMapping.regex;
+  const simpleRules = localPathMapping.simple;
+
   // --- Schedule Handlers ---
   const handleUpdateSchedule = (field: keyof ScheduleSettings, value: any) => {
     if (isLocked) return;
@@ -222,24 +384,18 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
     if (isLocked) return;
     setLocalSchedule(JSON.parse(JSON.stringify(savedSchedule)));
     if (savedSchedule.mode !== ScheduleMode.DISABLED) {
-      setActiveTab(savedSchedule.mode);
+      setActiveScheduleTab(savedSchedule.mode);
     } else {
-      setActiveTab(ScheduleMode.CRON);
+      setActiveScheduleTab(ScheduleMode.CRON);
     }
   };
 
   const handleSaveScheduleClick = async () => {
     if (isLocked) return;
-    
-    // Determine the effective settings based on the current view (tab) and inputs
-    const settingsToSave = deriveEffectiveSchedule(localSchedule, activeTab);
-    
-    // Call API
+    const settingsToSave = deriveEffectiveSchedule(localSchedule, activeScheduleTab);
     const success = await onSaveSchedule(settingsToSave);
     if (success) {
       setLocalSchedule(settingsToSave);
-      // Dirty state is cleared by the useEffect prop update, or we can clear it optimistically here if needed,
-      // but useEffect [savedSchedule] handles it correctly.
     }
   };
 
@@ -248,7 +404,6 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
     onSync();
   };
 
-  // Helper to toggle enable/disable for current active tab (Daily/Weekly)
   const toggleScheduleEnable = (targetMode: ScheduleMode) => {
       if (isLocked) return;
       if (localSchedule.mode === targetMode) {
@@ -258,7 +413,6 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
       }
   };
 
-  // If syncing or locked, apply grayscale filter to content sections
   const contentClass = isLocked ? "opacity-50 pointer-events-none grayscale transition-all" : "transition-all";
 
   return (
@@ -279,12 +433,13 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
       <div 
         className={`absolute 
           top-14 
-          /* Mobile: Open to left */
-          right-0 origin-top-right
-          /* Desktop: Center alignment */
-          md:left-1/2 md:right-auto md:origin-top md:-translate-x-1/2 
+          /* Mobile: Open to left (max width of screen) */
+          right-0 w-[90vw] max-w-[90vw] origin-top-right
           
-          w-80 md:w-[32rem] bg-gray-800/95 border border-white/10 rounded-xl shadow-2xl z-50 overflow-hidden backdrop-blur-xl
+          /* Desktop: Center alignment, wider */
+          md:left-1/2 md:right-auto md:origin-top md:-translate-x-1/2 md:w-[60rem] md:max-w-[60rem]
+          
+          bg-gray-800/95 border border-white/10 rounded-xl shadow-2xl z-50 overflow-hidden backdrop-blur-xl
           transition-all duration-200 ease-out
           ${isOpen ? 'opacity-100 scale-100 visible translate-y-0' : 'opacity-0 scale-95 invisible pointer-events-none -translate-y-2'}`}
       >
@@ -328,96 +483,123 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
             </div>
             </div>
 
-            {/* Section 2: Regex Preprocessing */}
+            {/* Section 2: Path Mapping (Tabs + Grid) */}
             <div className="p-4 bg-gray-900/40 border-b border-white/5 flex-none">
                 <div className="flex items-center justify-between mb-3">
-                    <h3 className="text-[10px] font-bold text-gray-500 uppercase tracking-widest">Regex Rules</h3>
-                    {localReplacements.length === 0 && (
-                        <button 
-                        onClick={handleAddRegex}
-                        className="p-1 rounded bg-gray-700/50 hover:bg-gray-600 text-gray-400 hover:text-white transition-colors"
-                        title="Add Rule"
-                        >
-                        <Plus size={14} />
-                        </button>
+                    <h3 className="text-[10px] font-bold text-gray-500 uppercase tracking-widest">Path Mapping</h3>
+                </div>
+
+                {/* Tabs for Path Mapping Mode */}
+                <div className="flex space-x-1 bg-black/30 p-1 rounded-lg mb-4">
+                  {[
+                    { id: PathMappingMode.SIMPLE, label: 'Simple Mapping', icon: Type },
+                    { id: PathMappingMode.REGEX, label: 'Regex Rules', icon: Code2 },
+                  ].map((tab) => (
+                    <button
+                      key={tab.id}
+                      onClick={() => setMappingMode(tab.id)}
+                      className={`flex-1 flex items-center justify-center space-x-2 py-1.5 rounded-md text-xs font-medium transition-all
+                        ${currentMappingMode === tab.id 
+                          ? 'bg-gray-700 text-plex-orange shadow-sm' 
+                          : 'text-gray-400 hover:text-gray-200 hover:bg-white/5'
+                        }`}
+                    >
+                        <tab.icon size={12} />
+                        <span>{tab.label}</span>
+                    </button>
+                  ))}
+                </div>
+
+                {/* Content Area */}
+                <div className="mb-4">
+                    {currentMappingMode === PathMappingMode.SIMPLE ? (
+                       // Simple Mode: Single Editor
+                       <div className="animate-in fade-in duration-200">
+                          <MappingGroupEditor 
+                             title="Path Mapping"
+                             subtitle="Map Local paths to Cloud paths using simple string matching"
+                             rules={simpleRules}
+                             onChange={updateSimpleGroup}
+                             isLocked={isLocked}
+                             borderColor={MAPPING_THEME.simple.borderColor}
+                             bgColor={MAPPING_THEME.simple.bgColor}
+                             leftPlaceholder="Local Path"
+                             rightPlaceholder="Cloud Path"
+                             leftInputClass={MAPPING_THEME.inputs.local}
+                             rightInputClass={MAPPING_THEME.inputs.cloud}
+                          />
+                       </div>
+                    ) : (
+                       // Regex Mode: 2x2 Grid
+                       <div className="grid grid-cols-1 md:grid-cols-2 gap-4 animate-in fade-in duration-200">
+                          {/* Row 1: Pre-Processing */}
+                          <MappingGroupEditor 
+                             title="Local Playlist"
+                             subtitle="Pre-Processing (Before Sync)"
+                             rules={regexRules.localPre}
+                             onChange={(rules) => updateRegexGroup('localPre', rules)}
+                             isLocked={isLocked}
+                             borderColor={MAPPING_THEME.local.borderColor}
+                             bgColor={MAPPING_THEME.local.bgColor}
+                          />
+
+                          <MappingGroupEditor 
+                             title="Remote Playlist"
+                             subtitle="Pre-Processing (Before Sync)"
+                             rules={regexRules.remotePre}
+                             onChange={(rules) => updateRegexGroup('remotePre', rules)}
+                             isLocked={isLocked}
+                             borderColor={MAPPING_THEME.remote.borderColor}
+                             bgColor={MAPPING_THEME.remote.bgColor}
+                          />
+
+                          {/* Row 2: Post-Processing */}
+                          <MappingGroupEditor 
+                             title="Local Playlist"
+                             subtitle="Post-Processing (After Sync / Result)"
+                             rules={regexRules.localPost}
+                             onChange={(rules) => updateRegexGroup('localPost', rules)}
+                             isLocked={isLocked}
+                             borderColor={MAPPING_THEME.local.borderColor}
+                             bgColor={MAPPING_THEME.local.bgColor}
+                          />
+
+                          <MappingGroupEditor 
+                             title="Remote Playlist"
+                             subtitle="Post-Processing (After Sync / Result)"
+                             rules={regexRules.remotePost}
+                             onChange={(rules) => updateRegexGroup('remotePost', rules)}
+                             isLocked={isLocked}
+                             borderColor={MAPPING_THEME.remote.borderColor}
+                             bgColor={MAPPING_THEME.remote.bgColor}
+                          />
+                       </div>
                     )}
                 </div>
 
-                <div className="space-y-2 mb-4 max-h-40 overflow-y-auto pr-1 custom-scrollbar">
-                {localReplacements.length === 0 ? (
-                    <div className="text-xs text-gray-600 italic text-center py-2 border border-dashed border-gray-700/50 rounded-lg">
-                        No regex replacements configured.
-                    </div>
-                ) : (
-                    localReplacements.map((regex) => (
-                    <div key={regex.id} className="flex items-center space-x-2 animate-in slide-in-from-left-2 duration-200">
-                        <div className="flex-1 min-w-0">
-                            <input 
-                                type="text" 
-                                placeholder="Pattern" 
-                                value={regex.pattern}
-                                onChange={(e) => handleUpdateRegex(regex.id, 'pattern', e.target.value)}
-                                className={`w-full bg-gray-900/80 border rounded-md px-2 py-1.5 text-xs text-gray-200 focus:outline-none focus:ring-1 transition-all placeholder-gray-600
-                                ${!regex.pattern && isRegexDirty ? 'border-red-500/30 focus:border-red-500' : 'border-gray-700 focus:border-plex-orange'}`}
-                            />
-                        </div>
-                        <div className="flex-none text-gray-600">
-                            <ArrowRightCircle size={12} />
-                        </div>
-                        <div className="flex-1 min-w-0">
-                            <input 
-                                type="text" 
-                                placeholder="Replacement" 
-                                value={regex.replacement}
-                                onChange={(e) => handleUpdateRegex(regex.id, 'replacement', e.target.value)}
-                                className="w-full bg-gray-900/80 border border-gray-700 rounded-md px-2 py-1.5 text-xs text-gray-200 focus:outline-none focus:border-plex-orange focus:ring-1 focus:ring-plex-orange transition-all placeholder-gray-600"
-                            />
-                        </div>
-                        <button 
-                            onClick={() => handleDeleteRegex(regex.id)}
-                            className="text-gray-600 hover:text-red-400 p-1.5 hover:bg-red-500/10 rounded transition-colors"
-                            title="Delete Rule"
-                        >
-                            <Trash2 size={14} />
-                        </button>
-                    </div>
-                    ))
-                )}
-                </div>
-
-                <div className="flex justify-between items-center gap-2">
-                     <button 
-                            onClick={handleAddRegex}
-                            className={`flex items-center space-x-1 px-2 py-1 rounded text-[10px] font-bold uppercase tracking-wide transition-colors ${localReplacements.length > 0 ? 'text-plex-orange hover:bg-plex-orange/10' : 'hidden'}`}
-                        >
-                            <Plus size={10} />
-                            <span>Add</span>
+                <div className="flex justify-end items-center gap-2">
+                    <button
+                        onClick={handleResetMapping}
+                        disabled={!isMappingDirty}
+                        className={`flex items-center justify-center space-x-1.5 px-3 py-1.5 rounded-md text-xs font-medium border transition-all
+                        ${isMappingDirty 
+                            ? 'bg-gray-800 border-gray-600 text-gray-300 hover:bg-gray-700 hover:text-white' 
+                            : 'bg-transparent border-transparent text-gray-700 cursor-not-allowed'}`}
+                    >
+                        <RotateCcw size={12} />
+                        <span>Revert</span>
+                    </button>
+                    <button
+                        onClick={handleSaveMappingClick}
+                        disabled={!isMappingDirty}
+                        className={`flex items-center justify-center space-x-1.5 px-3 py-1.5 rounded-md text-xs font-bold border transition-all
+                        ${isMappingDirty 
+                            ? 'bg-plex-orange border-plex-orange text-gray-900 hover:bg-yellow-500 shadow-lg shadow-plex-orange/10' 
+                            : 'bg-gray-800/30 border-gray-800/50 text-gray-600 cursor-not-allowed'}`}
+                    >
+                        <Save size={12} />
+                        <span>Save Rules</span>
                     </button>
-
-                    <div className="flex items-center gap-2 ml-auto">
-                        <button
-                            onClick={handleResetRegex}
-                            disabled={!isRegexDirty}
-                            className={`flex items-center justify-center space-x-1.5 px-3 py-1.5 rounded-md text-xs font-medium border transition-all
-                            ${isRegexDirty 
-                                ? 'bg-gray-800 border-gray-600 text-gray-300 hover:bg-gray-700 hover:text-white' 
-                                : 'bg-transparent border-transparent text-gray-700 cursor-not-allowed'}`}
-                        >
-                            <RotateCcw size={12} />
-                            <span>Revert</span>
-                        </button>
-                        <button
-                            onClick={handleSaveRegex}
-                            disabled={!isRegexDirty}
-                            className={`flex items-center justify-center space-x-1.5 px-3 py-1.5 rounded-md text-xs font-bold border transition-all
-                            ${isRegexDirty 
-                                ? 'bg-plex-orange border-plex-orange text-gray-900 hover:bg-yellow-500 shadow-lg shadow-plex-orange/10' 
-                                : 'bg-gray-800/30 border-gray-800/50 text-gray-600 cursor-not-allowed'}`}
-                        >
-                            <Save size={12} />
-                            <span>Save</span>
-                        </button>
-                    </div>
                 </div>
             </div>
 
@@ -436,9 +618,9 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                     ].map((tab) => (
                       <button
                         key={tab.id}
-                        onClick={() => setActiveTab(tab.id)}
+                        onClick={() => setActiveScheduleTab(tab.id)}
                         className={`flex-1 flex items-center justify-center space-x-2 py-1.5 rounded-md text-xs font-medium transition-all
-                          ${activeTab === tab.id 
+                          ${activeScheduleTab === tab.id 
                             ? 'bg-gray-700 text-plex-orange shadow-sm' 
                             : 'text-gray-400 hover:text-gray-200 hover:bg-white/5'
                           }`}
@@ -451,7 +633,7 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
 
                  {/* Tab Content */}
                  <div className="mb-4 min-h-[50px]">
-                    {activeTab === ScheduleMode.CRON && (
+                    {activeScheduleTab === ScheduleMode.CRON && (
                       <div className="space-y-2 animate-in fade-in duration-200">
                          <div className="flex items-center space-x-2">
                            <span className="text-gray-500 font-mono text-xs">Cron:</span>
@@ -469,7 +651,7 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                       </div>
                     )}
 
-                    {activeTab === ScheduleMode.DAILY && (
+                    {activeScheduleTab === ScheduleMode.DAILY && (
                        <div className="flex flex-col animate-in fade-in duration-200">
                           {/* Top Row: Checkbox + Label */}
                           <div className="flex items-center justify-start space-x-2 mb-2">
@@ -496,7 +678,7 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                        </div>
                     )}
 
-                    {activeTab === ScheduleMode.WEEKLY && (
+                    {activeScheduleTab === ScheduleMode.WEEKLY && (
                        <div className="flex flex-col animate-in fade-in duration-200">
                           {/* Top Row: Checkbox + Label */}
                           <div className="flex items-center justify-start space-x-2 mb-2">
@@ -563,7 +745,7 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                     </button>
                  </div>
 
-                 {/* Action Buttons (Mirrored from Regex) */}
+                 {/* Action Buttons */}
                  <div className="flex items-center gap-2 justify-end pt-3 border-t border-white/5">
                         <button
                             onClick={handleResetSchedule}
@@ -599,7 +781,7 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                 className={`w-full py-3 rounded-lg text-sm font-bold flex items-center justify-center gap-2 transition-all shadow-lg
                 ${isLocked 
                     ? 'bg-gray-700/30 text-gray-500 cursor-not-allowed border border-gray-700/50' 
-                    : isRegexDirty
+                    : isMappingDirty
                         ? 'bg-gray-800 text-gray-500 cursor-not-allowed border border-gray-700'
                         : 'bg-green-600 hover:bg-green-500 text-white border border-green-500 shadow-green-900/20 active:scale-[0.98]'
                 }`}
@@ -616,9 +798,9 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                     </>
                 )}
             </button>
-            {(isRegexDirty) && (
+            {(isMappingDirty) && (
                 <p className="text-[10px] text-plex-orange text-center mt-2">
-                    Please save regex changes before syncing.
+                    Please save path mapping changes before syncing.
                 </p>
             )}
         </div>

frontend/services/api.ts

@@ -1,4 +1,4 @@
-import { Playlist, ServerType, ApiResponse, PlexServerConnection, PlexConnectionSettings, PlexLibrary, RegexReplacement, SyncStrategy, ScheduleSettings } from '../types';
+import { Playlist, ServerType, ApiResponse, PlexServerConnection, PlexConnectionSettings, PlexLibrary, ReplacementRule, PathMappingConfig, PathMappingMode, PathMappingRules, SyncStrategy, ScheduleSettings } from '../types';
 
 const API_BASE = import.meta.env.VITE_API_BASE_URL || '';
 
@@ -41,21 +41,69 @@ const mapLibrary = (item: any): PlexLibrary => ({
   type: item.type ?? 'artist',
 });
 
-const mapRegexRules = (rules: any[]): RegexReplacement[] =>
+// Helper function to map raw rules array to ReplacementRule[]
+const mapReplacementRules = (rules: any[]): ReplacementRule[] =>
   (rules || []).map((rule, index) => ({
-    id: rule.id || `${rule.pattern || 'rule'}-${index}`,
-    pattern: rule.pattern || '',
-    replacement: rule.replacement || '',
+    id: rule.id || `${rule.search || 'rule'}-${index}-${Date.now()}`,
+    search: rule.search || rule.pattern || '',
+    replace: rule.replace || rule.replacement || '',
   }));
 
+// Helper function to map API path_mapping response to PathMappingConfig
+const mapPathMappingConfig = (data: any): PathMappingConfig => {
+  const defaultConfig: PathMappingConfig = {
+    mode: PathMappingMode.SIMPLE,
+    simple: [],
+    regex: {
+      localPre: [],
+      localPost: [],
+      remotePre: [],
+      remotePost: []
+    }
+  };
+
+  if (!data || !data.path_mapping) {
+    return defaultConfig;
+  }
+
+  const pm = data.path_mapping;
+  return {
+    mode: pm.mode === 'REGEX' ? PathMappingMode.REGEX : PathMappingMode.SIMPLE,
+    simple: mapReplacementRules(pm.simple || []),
+    regex: {
+      localPre: mapReplacementRules(pm.regex?.localPre || pm.regex?.local_pre || []),
+      localPost: mapReplacementRules(pm.regex?.localPost || pm.regex?.local_post || []),
+      remotePre: mapReplacementRules(pm.regex?.remotePre || pm.regex?.remote_pre || []),
+      remotePost: mapReplacementRules(pm.regex?.remotePost || pm.regex?.remote_post || [])
+    }
+  };
+};
+
+// Helper function to convert PathMappingConfig to API format
+const pathMappingToApi = (config: PathMappingConfig) => {
+  const rulesToApi = (rules: ReplacementRule[]) =>
+    rules.map(({ id, search, replace }) => ({ id, search, replace }));
+
+  return {
+    mode: config.mode,
+    simple: rulesToApi(config.simple),
+    regex: {
+      local_pre: rulesToApi(config.regex.localPre),
+      local_post: rulesToApi(config.regex.localPost),
+      remote_pre: rulesToApi(config.regex.remotePre),
+      remote_post: rulesToApi(config.regex.remotePost)
+    }
+  };
+};
+
 export const apiService = {
-  async getSettings(): Promise<ApiResponse<{ strategy: SyncStrategy; regex: RegexReplacement[]; connection: PlexConnectionSettings; localPath: string }>> {
+  async getSettings(): Promise<ApiResponse<{ strategy: SyncStrategy; pathMapping: PathMappingConfig; connection: PlexConnectionSettings; localPath: string }>> {
     const response = await fetch(`${API_BASE}/api/settings`);
     const result = await handleResponse<any>(response);
     if (result.status === 'success') {
       const mode = result.data.sync_mode as string;
       const strategy = MODE_TO_STRATEGY[mode] || SyncStrategy.LOCAL_OVERWRITE;
-      const regex = mapRegexRules(result.data.path_rules || []);
+      const pathMapping = mapPathMappingConfig(result.data);
       const connection: PlexConnectionSettings = {
         protocol: (result.data.scheme as 'http' | 'https') || 'https',
         address: result.data.server_url || '',
@@ -63,9 +111,9 @@ export const apiService = {
         token: result.data.token || '',
         libraryName: result.data.library_name || '',
       };
-      return { status: 'success', data: { strategy, regex, connection, localPath: result.data.local_path || '' } };
+      return { status: 'success', data: { strategy, pathMapping, connection, localPath: result.data.local_path || '' } };
     }
-    return result as ApiResponse<any> as ApiResponse<{ strategy: SyncStrategy; regex: RegexReplacement[]; connection: PlexConnectionSettings; localPath: string }>;
+    return result as ApiResponse<any> as ApiResponse<{ strategy: SyncStrategy; pathMapping: PathMappingConfig; connection: PlexConnectionSettings; localPath: string }>;
   },
 
   async updateSyncStrategy(strategy: SyncStrategy): Promise<ApiResponse<{ sync_mode: string }>> {
@@ -78,9 +126,9 @@ export const apiService = {
     return handleResponse(response);
   },
 
-  async saveRegexRules(replacements: RegexReplacement[]): Promise<ApiResponse<{ rules: RegexReplacement[] }>> {
-    const payload = { rules: replacements.map(({ pattern, replacement }) => ({ pattern, replacement })) };
-    const response = await fetch(`${API_BASE}/api/settings/regex-rules`, {
+  async savePathMapping(config: PathMappingConfig): Promise<ApiResponse<null>> {
+    const payload = pathMappingToApi(config);
+    const response = await fetch(`${API_BASE}/api/settings/path-mapping`, {
       method: 'PUT',
       headers: { 'Content-Type': 'application/json' },
       body: JSON.stringify(payload),
@@ -170,7 +218,7 @@ export const apiService = {
     return result as ApiResponse<{ token: string; serverInfo: PlexServerConnection }>;
   },
 
-  async syncPlaylists(strategy: SyncStrategy, _regexRules: RegexReplacement[], localPath?: string): Promise<ApiResponse<null>> {
+  async syncPlaylists(strategy: SyncStrategy, _pathMapping: PathMappingConfig, localPath?: string): Promise<ApiResponse<null>> {
     const response = await fetch(`${API_BASE}/api/sync`, {
       method: 'POST',
       headers: { 'Content-Type': 'application/json' },

frontend/types.ts

@@ -34,6 +34,30 @@ export enum SyncState {
   ERROR = 'ERROR'
 }
 
+export interface ReplacementRule {
+  id: string;
+  search: string;
+  replace: string;
+}
+
+export interface PathMappingRules {
+  localPre: ReplacementRule[];
+  localPost: ReplacementRule[];
+  remotePre: ReplacementRule[];
+  remotePost: ReplacementRule[];
+}
+
+export enum PathMappingMode {
+  SIMPLE = 'SIMPLE',
+  REGEX = 'REGEX'
+}
+
+export interface PathMappingConfig {
+  mode: PathMappingMode;
+  simple: ReplacementRule[];
+  regex: PathMappingRules;
+}
+
 export interface RegexReplacement {
   id: string;
   pattern: string;

sample-front-end/App.tsx

@@ -1,5 +1,7 @@
+
+
 import React, { useEffect, useState, useCallback, useRef } from 'react';
-import { Playlist, ServerType, SyncStrategy, PlexServerConnection, PathMappingConfig, PathMappingMode, SyncState, ScheduleSettings, ScheduleMode } from './types';
+import { Playlist, ServerType, SyncStrategy, PlexServerConnection, PathMappingConfig, PathMappingMode, SyncState, ScheduleSettings, ScheduleMode, BackupSettings } from './types';
 import { apiService } from './services/api';
 import { 
   STRIPE_BASE_SPEED,
@@ -157,6 +159,12 @@ const App: React.FC = () => {
     autoWatch: false
   });
 
+  // Backup State
+  const [backupSettings, setBackupSettings] = useState<BackupSettings>({
+    enabled: false,
+    retentionCount: 5
+  });
+
   // Toast Notification System
   const [toasts, setToasts] = useState<Toast[]>([]);
   const timeoutsRef = useRef<{[key: number]: ReturnType<typeof setTimeout>}>({});
@@ -305,6 +313,17 @@ const App: React.FC = () => {
     addToast('Path mapping rules have been saved.');
   };
 
+  // Handle Backup Settings Save
+  const handleSaveBackupSettings = async (settings: BackupSettings) => {
+    const result = await apiService.saveBackupSettings(settings);
+    if (result.status === 'success') {
+      setBackupSettings(settings);
+      addToast('Backup settings have been saved.');
+    } else {
+      addToast('Failed to save backup settings.');
+    }
+  };
+
   // Handle Schedule Save
   const handleSaveSchedule = async (settings: ScheduleSettings): Promise<boolean> => {
     // Call API (validation happens in Mock)
@@ -719,6 +738,8 @@ const App: React.FC = () => {
                 onSelect={handleStrategyChange}
                 savedPathMapping={pathMappingConfig}
                 onSavePathMapping={handleSavePathMapping}
+                savedBackup={backupSettings}
+                onSaveBackup={handleSaveBackupSettings}
                 savedSchedule={scheduleSettings}
                 onSaveSchedule={handleSaveSchedule}
                 syncState={syncState}

sample-front-end/components/ConnectionModal.tsx

@@ -141,8 +141,14 @@ const ConnectionModal: React.FC<ConnectionModalProps> = ({ isOpen, onClose, onCo
   const isConnected = !!connectedServerInfo;
 
   return (
-    <div className="fixed inset-0 z-50 flex items-center justify-center p-4 bg-black/60 backdrop-blur-sm">
-      <div className="bg-gray-900 border border-gray-700 rounded-xl shadow-2xl w-full max-w-md overflow-hidden animate-in fade-in zoom-in duration-200 flex flex-col max-h-[90vh]">
+    <div 
+      className="fixed inset-0 z-50 flex items-center justify-center p-4 bg-black/60 backdrop-blur-sm"
+      onClick={onClose}
+    >
+      <div 
+        className="bg-gray-900 border border-gray-700 rounded-xl shadow-2xl w-full max-w-md overflow-hidden animate-in fade-in zoom-in duration-200 flex flex-col max-h-[90vh]"
+        onClick={(e) => e.stopPropagation()}
+      >
         
         {/* Header */}
         <div className="px-6 py-4 bg-gray-800 border-b border-gray-700 flex items-center justify-between flex-none">

sample-front-end/components/StrategySelector.tsx

@@ -1,5 +1,5 @@
 import React, { useState, useRef, useEffect } from 'react';
-import { SyncStrategy, ReplacementRule, PathMappingConfig, PathMappingRules, PathMappingMode, SyncState, ScheduleSettings, ScheduleMode } from '../types';
+import { SyncStrategy, ReplacementRule, PathMappingConfig, PathMappingRules, PathMappingMode, SyncState, ScheduleSettings, ScheduleMode, BackupSettings } from '../types';
 import { 
   ArrowRightCircle, 
   ArrowLeftCircle, 
@@ -16,10 +16,12 @@ import {
   Calendar,
   Clock,
   Repeat,
-  CheckSquare,
-  Square,
   Type,
-  Code2
+  Code2,
+  Link,
+  Archive,
+  History,
+  Eye
 } from 'lucide-react';
 
 interface StrategyOption {
@@ -90,17 +92,12 @@ const MAPPING_THEME = {
 const deriveEffectiveSchedule = (schedule: ScheduleSettings, tab: ScheduleMode): ScheduleSettings => {
   const derived = { ...schedule };
   
-  if (tab === ScheduleMode.CRON) {
-     derived.mode = derived.cronExpression.trim() !== '' ? ScheduleMode.CRON : ScheduleMode.DISABLED;
+  // Unified logic: If the mode matches the tab, we keep it (Enabled).
+  // If the mode doesn't match (e.g. it was DISABLED), then in the context of this tab, it remains Disabled until the user toggles the switch.
+  if (derived.mode === tab) {
+    derived.mode = tab;
   } else {
-    // For Daily/Weekly
-    // If the mode matches the tab, we keep it (Enabled).
-    // If the mode doesn't match (e.g. it was CRON or DISABLED), then in the context of this tab, it is effectively Disabled until the user checks the box.
-    if (derived.mode === tab) {
-      derived.mode = tab;
-    } else {
-      derived.mode = ScheduleMode.DISABLED;
-    }
+    derived.mode = ScheduleMode.DISABLED;
   }
   return derived;
 };
@@ -186,7 +183,7 @@ const MappingGroupEditor: React.FC<MappingGroupEditorProps> = ({
                   onChange={(e) => handleUpdate(rule.id, 'search', e.target.value)}
                   className={`flex-1 min-w-0 border rounded px-1.5 py-1 text-xs focus:outline-none transition-colors ${leftInputClass || defaultInputStyle}`}
                 />
-                <ArrowRightCircle size={10} className="text-gray-600 flex-none opacity-50" />
+                <Link size={12} className="text-gray-600 flex-none opacity-50" />
                 <input 
                   type="text" 
                   placeholder={rightPlaceholder}
@@ -213,6 +210,8 @@ interface StrategySelectorProps {
   onSelect: (strategy: SyncStrategy, label: string) => void;
   savedPathMapping: PathMappingConfig;
   onSavePathMapping: (config: PathMappingConfig) => void;
+  savedBackup: BackupSettings;
+  onSaveBackup: (settings: BackupSettings) => void;
   savedSchedule: ScheduleSettings;
   onSaveSchedule: (settings: ScheduleSettings) => Promise<boolean>;
   syncState: SyncState;
@@ -224,6 +223,8 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
   onSelect, 
   savedPathMapping, 
   onSavePathMapping,
+  savedBackup,
+  onSaveBackup,
   savedSchedule,
   onSaveSchedule,
   syncState,
@@ -236,6 +237,10 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
   const [localPathMapping, setLocalPathMapping] = useState<PathMappingConfig>(savedPathMapping);
   const [isMappingDirty, setIsMappingDirty] = useState(false);
 
+  // Local state for Backup Settings
+  const [localBackup, setLocalBackup] = useState<BackupSettings>(savedBackup);
+  const [isBackupDirty, setIsBackupDirty] = useState(false);
+
   // Local state for Schedule editing
   const [localSchedule, setLocalSchedule] = useState<ScheduleSettings>(savedSchedule);
   const [isScheduleDirty, setIsScheduleDirty] = useState(false);
@@ -254,6 +259,11 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
     setIsMappingDirty(false);
   }, [savedPathMapping]);
 
+  useEffect(() => {
+    setLocalBackup(JSON.parse(JSON.stringify(savedBackup)));
+    setIsBackupDirty(false);
+  }, [savedBackup]);
+
   useEffect(() => {
     setLocalSchedule(JSON.parse(JSON.stringify(savedSchedule)));
     if (savedSchedule.mode !== ScheduleMode.DISABLED) {
@@ -268,6 +278,12 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
     setIsMappingDirty(isDifferent);
   }, [localPathMapping, savedPathMapping]);
 
+  // Check dirty state for backup
+  useEffect(() => {
+    const isDifferent = JSON.stringify(localBackup) !== JSON.stringify(savedBackup);
+    setIsBackupDirty(isDifferent);
+  }, [localBackup, savedBackup]);
+
   // Check dirty state for Schedule (including Active Tab changes)
   useEffect(() => {
     const effectiveLocal = deriveEffectiveSchedule(localSchedule, activeScheduleTab);
@@ -351,6 +367,22 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
   const regexRules = localPathMapping.regex;
   const simpleRules = localPathMapping.simple;
 
+  // --- Backup Handlers ---
+  const handleUpdateBackup = (field: keyof BackupSettings, value: any) => {
+    if (isLocked) return;
+    setLocalBackup(prev => ({ ...prev, [field]: value }));
+  };
+
+  const handleResetBackup = () => {
+    if (isLocked) return;
+    setLocalBackup(JSON.parse(JSON.stringify(savedBackup)));
+  };
+
+  const handleSaveBackupClick = () => {
+    if (isLocked) return;
+    onSaveBackup(localBackup);
+  };
+
   // --- Schedule Handlers ---
   const handleUpdateSchedule = (field: keyof ScheduleSettings, value: any) => {
     if (isLocked) return;
@@ -469,6 +501,80 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
             </div>
             </div>
 
+            {/* Section 1.5: Backup Retention */}
+            <div className="px-4 py-3 bg-gray-900/40 border-b border-white/5 flex-none">
+              <div className="flex items-center justify-between mb-3">
+                 <h3 className="text-[10px] font-bold text-gray-500 uppercase tracking-widest">Backup Retention</h3>
+              </div>
+              
+              <div className="flex flex-col space-y-3">
+                 <div className="flex items-center justify-between">
+                    <div className="flex items-center space-x-2">
+                       <div className="p-1.5 rounded-lg bg-indigo-500/10 border border-indigo-500/20 text-indigo-400">
+                          <Archive size={16} />
+                       </div>
+                       <div className="flex flex-col">
+                          <span className="text-sm font-medium text-gray-200">Enable Backups</span>
+                          <span className="text-[10px] text-gray-500">Create a copy before changes</span>
+                       </div>
+                    </div>
+
+                    <button 
+                      onClick={() => handleUpdateBackup('enabled', !localBackup.enabled)}
+                      className={`relative inline-flex h-6 w-11 items-center rounded-full transition-colors focus:outline-none focus:ring-2 focus:ring-plex-orange focus:ring-offset-2 focus:ring-offset-gray-900 ${localBackup.enabled ? 'bg-plex-orange' : 'bg-gray-700'}`}
+                    >
+                      <span className={`inline-block h-4 w-4 transform rounded-full bg-white transition-transform ${localBackup.enabled ? 'translate-x-6' : 'translate-x-1'}`} />
+                    </button>
+                 </div>
+                 
+                 {/* Expanded Config */}
+                 <div className={`overflow-hidden transition-all duration-300 ${localBackup.enabled ? 'max-h-20 opacity-100' : 'max-h-0 opacity-50'}`}>
+                    <div className="flex items-center justify-between p-2.5 rounded-lg bg-black/20 border border-white/5">
+                        <div className="flex items-center space-x-2">
+                           <History size={14} className="text-gray-500" />
+                           <span className="text-xs text-gray-400">Max versions to keep:</span>
+                        </div>
+                        <div className="flex items-center space-x-2">
+                            <input 
+                               type="number" 
+                               min="1" 
+                               max="100" 
+                               value={localBackup.retentionCount}
+                               onChange={(e) => handleUpdateBackup('retentionCount', parseInt(e.target.value) || 1)}
+                               className="w-16 bg-gray-800 border border-gray-700 text-center text-sm rounded py-1 text-white focus:border-plex-orange focus:outline-none"
+                            />
+                            <span className="text-[10px] text-gray-600 italic">Oldest deleted automatically</span>
+                        </div>
+                    </div>
+                 </div>
+
+                 <div className="flex justify-end items-center gap-2 pt-1">
+                    <button
+                        onClick={handleResetBackup}
+                        disabled={!isBackupDirty}
+                        className={`flex items-center justify-center space-x-1.5 px-3 py-1.5 rounded-md text-xs font-medium border transition-all
+                        ${isBackupDirty 
+                            ? 'bg-gray-800 border-gray-600 text-gray-300 hover:bg-gray-700 hover:text-white' 
+                            : 'bg-transparent border-transparent text-gray-700 cursor-not-allowed'}`}
+                    >
+                        <RotateCcw size={12} />
+                        <span>Revert</span>
+                    </button>
+                    <button
+                        onClick={handleSaveBackupClick}
+                        disabled={!isBackupDirty}
+                        className={`flex items-center justify-center space-x-1.5 px-3 py-1.5 rounded-md text-xs font-bold border transition-all
+                        ${isBackupDirty 
+                            ? 'bg-plex-orange border-plex-orange text-gray-900 hover:bg-yellow-500 shadow-lg shadow-plex-orange/10' 
+                            : 'bg-gray-800/30 border-gray-800/50 text-gray-600 cursor-not-allowed'}`}
+                    >
+                        <Save size={12} />
+                        <span>Save</span>
+                    </button>
+                 </div>
+              </div>
+            </div>
+
             {/* Section 2: Path Mapping (Tabs + Grid) */}
             <div className="p-4 bg-gray-900/40 border-b border-white/5 flex-none">
                 <div className="flex items-center justify-between mb-3">
@@ -620,35 +726,49 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                  {/* Tab Content */}
                  <div className="mb-4 min-h-[50px]">
                     {activeScheduleTab === ScheduleMode.CRON && (
-                      <div className="space-y-2 animate-in fade-in duration-200">
-                         <div className="flex items-center space-x-2">
-                           <span className="text-gray-500 font-mono text-xs">Cron:</span>
-                           <input 
-                             type="text" 
-                             value={localSchedule.cronExpression}
-                             onChange={(e) => handleUpdateSchedule('cronExpression', e.target.value)}
-                             placeholder="0 0 * * *"
-                             className="flex-1 bg-gray-800 border border-gray-700 rounded-md px-2.5 py-1.5 text-xs text-gray-200 font-mono focus:border-plex-orange focus:outline-none focus:ring-1 focus:ring-plex-orange placeholder-gray-600"
-                           />
+                      <div className="flex flex-col animate-in fade-in duration-200">
+                         {/* Top Row: Label + Switch */}
+                         <div className="flex items-center justify-between mb-3 px-1">
+                           <span className="text-xs text-gray-400 font-medium">Enable Cron Schedule</span>
+                           <button 
+                               onClick={() => toggleScheduleEnable(ScheduleMode.CRON)}
+                               className={`relative inline-flex h-6 w-11 items-center rounded-full transition-colors focus:outline-none focus:ring-2 focus:ring-plex-orange focus:ring-offset-2 focus:ring-offset-gray-900 ${localSchedule.mode === ScheduleMode.CRON ? 'bg-plex-orange' : 'bg-gray-700'}`}
+                           >
+                               <span className={`inline-block h-4 w-4 transform rounded-full bg-white transition-transform ${localSchedule.mode === ScheduleMode.CRON ? 'translate-x-6' : 'translate-x-1'}`} />
+                           </button>
+                         </div>
+
+                         {/* Content */}
+                         <div className={`space-y-2 transition-opacity duration-200 ${localSchedule.mode !== ScheduleMode.CRON ? 'opacity-50 pointer-events-none' : ''}`}>
+                             <div className="flex items-center space-x-2">
+                               <span className="text-gray-500 font-mono text-xs">Cron:</span>
+                               <input 
+                                 type="text" 
+                                 value={localSchedule.cronExpression}
+                                 onChange={(e) => handleUpdateSchedule('cronExpression', e.target.value)}
+                                 placeholder="0 0 * * *"
+                                 disabled={localSchedule.mode !== ScheduleMode.CRON}
+                                 className="flex-1 bg-gray-800 border border-gray-700 rounded-md px-2.5 py-1.5 text-xs text-gray-200 font-mono focus:border-plex-orange focus:outline-none focus:ring-1 focus:ring-plex-orange placeholder-gray-600"
+                               />
+                             </div>
+                             <p className="text-[10px] text-gray-500">
+                               Unix-cron format.
+                             </p>
                          </div>
-                         <p className="text-[10px] text-gray-500">
-                           Unix-cron format. Leave empty to disable schedule.
-                         </p>
                       </div>
                     )}
 
                     {activeScheduleTab === ScheduleMode.DAILY && (
                        <div className="flex flex-col animate-in fade-in duration-200">
-                          {/* Top Row: Checkbox + Label */}
-                          <div className="flex items-center justify-start space-x-2 mb-2">
+                          {/* Top Row: Label + Switch */}
+                          <div className="flex items-center justify-between mb-3 px-1">
+                            <span className="text-xs text-gray-400 font-medium">Enable Daily Run</span>
                             <button 
                                 onClick={() => toggleScheduleEnable(ScheduleMode.DAILY)}
-                                className={`transition-colors flex-none ${localSchedule.mode === ScheduleMode.DAILY ? 'text-plex-orange' : 'text-gray-500 hover:text-gray-400'}`}
-                                title={localSchedule.mode === ScheduleMode.DAILY ? "Schedule Enabled" : "Schedule Disabled"}
+                                className={`relative inline-flex h-6 w-11 items-center rounded-full transition-colors focus:outline-none focus:ring-2 focus:ring-plex-orange focus:ring-offset-2 focus:ring-offset-gray-900 ${localSchedule.mode === ScheduleMode.DAILY ? 'bg-plex-orange' : 'bg-gray-700'}`}
                             >
-                                {localSchedule.mode === ScheduleMode.DAILY ? <CheckSquare size={16} /> : <Square size={16} />}
+                                <span className={`inline-block h-4 w-4 transform rounded-full bg-white transition-transform ${localSchedule.mode === ScheduleMode.DAILY ? 'translate-x-6' : 'translate-x-1'}`} />
                             </button>
-                            <label className="text-xs text-gray-400 font-medium">Run daily at:</label>
                           </div>
                           
                           {/* Bottom Row: Centered Native Time Input */}
@@ -666,16 +786,15 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
 
                     {activeScheduleTab === ScheduleMode.WEEKLY && (
                        <div className="flex flex-col animate-in fade-in duration-200">
-                          {/* Top Row: Checkbox + Label */}
-                          <div className="flex items-center justify-start space-x-2 mb-2">
-                              <button 
+                          {/* Top Row: Label + Switch */}
+                          <div className="flex items-center justify-between mb-3 px-1">
+                            <span className="text-xs text-gray-400 font-medium">Enable Weekly Run</span>
+                            <button 
                                 onClick={() => toggleScheduleEnable(ScheduleMode.WEEKLY)}
-                                className={`transition-colors flex-none ${localSchedule.mode === ScheduleMode.WEEKLY ? 'text-plex-orange' : 'text-gray-500 hover:text-gray-400'}`}
-                                title={localSchedule.mode === ScheduleMode.WEEKLY ? "Schedule Enabled" : "Schedule Disabled"}
-                              >
-                                  {localSchedule.mode === ScheduleMode.WEEKLY ? <CheckSquare size={16} /> : <Square size={16} />}
-                              </button>
-                              <label className="text-xs text-gray-400 font-medium">Run on days:</label>
+                                className={`relative inline-flex h-6 w-11 items-center rounded-full transition-colors focus:outline-none focus:ring-2 focus:ring-plex-orange focus:ring-offset-2 focus:ring-offset-gray-900 ${localSchedule.mode === ScheduleMode.WEEKLY ? 'bg-plex-orange' : 'bg-gray-700'}`}
+                            >
+                                <span className={`inline-block h-4 w-4 transform rounded-full bg-white transition-transform ${localSchedule.mode === ScheduleMode.WEEKLY ? 'translate-x-6' : 'translate-x-1'}`} />
+                            </button>
                           </div>
 
                           {/* Middle Row: Full Width Capsules */}
@@ -714,20 +833,22 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                     )}
                  </div>
 
-                 {/* Auto Watch Checkbox */}
-                 <div className="flex items-center mb-4 px-1">
+                 {/* Auto Watch Switch */}
+                 <div className="flex items-center justify-between mb-4 mt-2 px-1">
+                    <div className="flex items-center space-x-2">
+                        <div className="p-1.5 rounded-lg bg-orange-500/10 border border-orange-500/20 text-orange-400">
+                             <Eye size={16} />
+                        </div>
+                        <div className="flex flex-col">
+                             <span className="text-sm font-medium text-gray-200">Watch Local Changes</span>
+                             <span className="text-[10px] text-gray-500">Auto-sync when local playlist updates</span>
+                        </div>
+                    </div>
                     <button 
-                      onClick={() => handleUpdateSchedule('autoWatch', !localSchedule.autoWatch)}
-                      className="flex items-center space-x-2 group"
+                        onClick={() => handleUpdateSchedule('autoWatch', !localSchedule.autoWatch)}
+                        className={`relative inline-flex h-6 w-11 items-center rounded-full transition-colors focus:outline-none focus:ring-2 focus:ring-plex-orange focus:ring-offset-2 focus:ring-offset-gray-900 ${localSchedule.autoWatch ? 'bg-plex-orange' : 'bg-gray-700'}`}
                     >
-                       {localSchedule.autoWatch ? (
-                         <CheckSquare size={16} className="text-plex-orange" />
-                       ) : (
-                         <Square size={16} className="text-gray-600 group-hover:text-gray-400" />
-                       )}
-                       <span className={`text-xs ${localSchedule.autoWatch ? 'text-gray-200' : 'text-gray-500 group-hover:text-gray-400'}`}>
-                         Watch for local playlist changes
-                       </span>
+                        <span className={`inline-block h-4 w-4 transform rounded-full bg-white transition-transform ${localSchedule.autoWatch ? 'translate-x-6' : 'translate-x-1'}`} />
                     </button>
                  </div>
 
@@ -767,7 +888,7 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                 className={`w-full py-3 rounded-lg text-sm font-bold flex items-center justify-center gap-2 transition-all shadow-lg
                 ${isLocked 
                     ? 'bg-gray-700/30 text-gray-500 cursor-not-allowed border border-gray-700/50' 
-                    : isMappingDirty
+                    : isMappingDirty || isBackupDirty
                         ? 'bg-gray-800 text-gray-500 cursor-not-allowed border border-gray-700'
                         : 'bg-green-600 hover:bg-green-500 text-white border border-green-500 shadow-green-900/20 active:scale-[0.98]'
                 }`}
@@ -784,9 +905,9 @@ const StrategySelector: React.FC<StrategySelectorProps> = ({
                     </>
                 )}
             </button>
-            {(isMappingDirty) && (
+            {(isMappingDirty || isBackupDirty) && (
                 <p className="text-[10px] text-plex-orange text-center mt-2">
-                    Please save path mapping changes before syncing.
+                    Please save pending changes (Backups/Path Mapping) before syncing.
                 </p>
             )}
         </div>

sample-front-end/services/api.ts

@@ -2,7 +2,8 @@
 
 
 
-import { Playlist, ServerType, ApiResponse, PlexServerConnection, PlexConnectionSettings, PlexLibrary, SyncStrategy, PathMappingConfig, ScheduleSettings, ScheduleMode } from '../types';
+
+import { Playlist, ServerType, ApiResponse, PlexServerConnection, PlexConnectionSettings, PlexLibrary, SyncStrategy, PathMappingConfig, ScheduleSettings, ScheduleMode, BackupSettings } from '../types';
 import { MOCK_LOCAL_PLAYLISTS, MOCK_CLOUD_PLAYLISTS } from './mockData';
 
 const SIMULATE_DELAY_MS = 800;
@@ -220,5 +221,13 @@ export const apiService = {
         resolve({ data: null, status: 'success', message: 'Schedule updated successfully' });
       }, 500);
     });
+  },
+
+  saveBackupSettings: async (settings: BackupSettings): Promise<ApiResponse<null>> => {
+    return new Promise((resolve) => {
+      setTimeout(() => {
+        resolve({ data: null, status: 'success', message: 'Backup settings saved' });
+      }, 500);
+    });
   }
 };

sample-front-end/types.ts

@@ -59,6 +59,11 @@ export interface PathMappingConfig {
   regex: PathMappingRules;
 }
 
+export interface BackupSettings {
+  enabled: boolean;
+  retentionCount: number;
+}
+
 export enum ScheduleMode {
   DISABLED = 'DISABLED',
   CRON = 'CRON',