diff --git a/web/backend/src/MediaPlayer.ts b/web/backend/src/MediaPlayer.ts
index 5b560ec..5018d61 100644
--- a/web/backend/src/MediaPlayer.ts
+++ b/web/backend/src/MediaPlayer.ts
@@ -37,6 +37,7 @@ enum UserEvent {
     FavoritesUpdate     = "favorites_update",
     MetadataUpdate      = "metadata_update",
     MPDUpdate           = "mpd_update",
+    PlaybackError       = "playback_error",
 }
 
 export interface Features {
@@ -57,6 +58,9 @@ export class MediaPlayer {
     private dataBuffer: string = '';
     private metadata: Map<string, LinkMetadata> = new Map();
     private bonjourInstance: Bonjour | null = null;
+    private playbackErrors: Map<string, string> = new Map();
+    private currentFile: string | null = null;
+    private lastLoadCandidate: string | null = null;
 
     constructor() {
         this.socket = this.tryRespawnPlayerProcess();
@@ -152,7 +156,8 @@ export class MediaPlayer {
                 const playlist = response.data as PlaylistItem[];
                 return playlist.map((item: PlaylistItem) => ({
                     ...item,
-                    metadata: this.metadata.get(item.filename) || {}
+                    metadata: this.metadata.get(item.filename) || {},
+                    playbackError: this.playbackErrors.get(item.filename)
                 }));
             });
     }
@@ -352,6 +357,8 @@ export class MediaPlayer {
     }
 
     private async loadFile(url: string, mode: string, fetchMetadata: boolean = true, options: string[] = []) {
+        this.lastLoadCandidate = url;
+        this.playbackErrors.delete(url);
         this.modify(UserEvent.PlaylistUpdate, () => this.writeCommand("loadfile", [url, mode, "-1", options.join(',')]));
 
         if (fetchMetadata) {
@@ -470,6 +477,24 @@ export class MediaPlayer {
                             this.pendingCommands.delete(response.request_id);
                         }
                     } else if (response.event) {
+                        if (response.event === "start-file") {
+                            // Clear any previous error for the file that is starting
+                            const file = response.file || this.lastLoadCandidate;
+                            if (file) {
+                                this.currentFile = file;
+                                this.playbackErrors.delete(file);
+                            }
+                        } else if (response.event === "end-file" && response.reason === "error") {
+                            const file = response.file || this.currentFile || this.lastLoadCandidate || "Unknown file";
+                            const errorMessage = response.error || response["file-error"] || "Unknown playback error";
+
+                            this.playbackErrors.set(file, errorMessage);
+                            this.handleEvent(UserEvent.PlaybackError, {
+                                filename: file,
+                                error: errorMessage
+                            });
+                        }
+
                         this.handleEvent(UserEvent.MPDUpdate, response);
                     } else {
                         console.log(response);
diff --git a/web/backend/src/types.ts b/web/backend/src/types.ts
index c88aee0..3630cdd 100644
--- a/web/backend/src/types.ts
+++ b/web/backend/src/types.ts
@@ -29,4 +29,5 @@ export interface PlaylistItem {
     playing?: boolean;
     current?: boolean;
     metadata?: LinkMetadata;
-} 
+    playbackError?: string;
+}
diff --git a/web/frontend/src/api/player.tsx b/web/frontend/src/api/player.tsx
index f417904..7740df9 100644
--- a/web/frontend/src/api/player.tsx
+++ b/web/frontend/src/api/player.tsx
@@ -28,6 +28,7 @@ export interface PlaylistItem {
   id: number;
   playing: boolean | null;
   metadata?: Metadata;
+  playbackError?: string;
 }
 
 export const getDisplayTitle = (item: PlaylistItem): string => {
@@ -62,6 +63,7 @@ export enum ServerEvent {
   FavoritesUpdate     = "favorites_update",
   MetadataUpdate      = "metadata_update",
   MPDUpdate           = "mpd_update",
+  PlaybackError       = "playback_error",
   ScreenShare         = "screen_share",
 }
 
diff --git a/web/frontend/src/components/App.tsx b/web/frontend/src/components/App.tsx
index 5e56f69..5ef1e23 100644
--- a/web/frontend/src/components/App.tsx
+++ b/web/frontend/src/components/App.tsx
@@ -199,6 +199,7 @@ const App: React.FC = () => {
       case ServerEvent.NowPlayingUpdate:
       case ServerEvent.MetadataUpdate:
       case ServerEvent.MPDUpdate:
+      case ServerEvent.PlaybackError:
         fetchPlaylist();
         fetchNowPlaying();
         break;
diff --git a/web/frontend/src/components/SongRow.tsx b/web/frontend/src/components/SongRow.tsx
index 462336b..d2c29c8 100644
--- a/web/frontend/src/components/SongRow.tsx
+++ b/web/frontend/src/components/SongRow.tsx
@@ -1,6 +1,6 @@
 import classNames from 'classnames';
 import React, { useState, useRef, useEffect, ReactNode } from 'react';
-import { FaPlay, FaVolumeUp, FaVolumeOff } from 'react-icons/fa';
+import { FaPlay, FaVolumeUp, FaVolumeOff, FaExclamationTriangle } from 'react-icons/fa';
 import { getDisplayTitle, PlaylistItem } from '../api/player';
 
 export enum PlayState {
@@ -19,6 +19,7 @@ export interface SongRowProps {
 
 const SongRow: React.FC<SongRowProps> = ({ song, auxControl, playState, onDelete, onPlay }) => {
   const [showDeleteConfirm, setShowDeleteConfirm] = useState(false);
+  const [showErrorDetails, setShowErrorDetails] = useState(false);
   const buttonRef = useRef<HTMLButtonElement>(null);
   
   useEffect(() => {
@@ -38,6 +39,7 @@ const SongRow: React.FC<SongRowProps> = ({ song, auxControl, playState, onDelete
   }, [showDeleteConfirm]);
   
   const displayTitle = getDisplayTitle(song);
+  const hasError = !!song.playbackError;
   
   return (
     <div className={classNames(
@@ -46,16 +48,46 @@ const SongRow: React.FC<SongRowProps> = ({ song, auxControl, playState, onDelete
       "bg-black/30": playState === PlayState.NotPlaying,
     })}>
       <div className="flex flex-row gap-2">
-        <button 
-          className="text-white/40 hover:text-white transition-colors px-3 py-1 rounded"
-          onClick={onPlay}
-        >
-          {
-            playState === PlayState.Playing ? <FaVolumeUp size={12} /> 
-            : playState === PlayState.Paused ? <FaVolumeOff size={12} /> 
-            : <FaPlay size={12} />
-          }
-        </button>
+        <div className="relative">
+          <button 
+            className={classNames(
+              "transition-colors px-3 py-1 rounded", 
+              hasError ? "text-amber-300 hover:text-amber-100" : "text-white/40 hover:text-white"
+            )}
+            onClick={() => {
+              if (hasError) {
+                setShowErrorDetails((prev) => !prev);
+              } else {
+                onPlay();
+              }
+            }}
+            onMouseEnter={() => {
+              if (hasError) {
+                setShowErrorDetails(true);
+              }
+            }}
+            onMouseLeave={() => {
+              if (hasError) {
+                setShowErrorDetails(false);
+              }
+            }}
+            title={hasError ? song.playbackError : undefined}
+          >
+            {
+              hasError ? <FaExclamationTriangle size={12} /> : 
+              playState === PlayState.Playing ? <FaVolumeUp size={12} /> 
+              : playState === PlayState.Paused ? <FaVolumeOff size={12} /> 
+              : <FaPlay size={12} />
+            }
+          </button>
+
+          {hasError && showErrorDetails && (
+            <div className="absolute z-10 top-full left-0 mt-1 w-64 p-2 text-xs text-white bg-red-600/90 rounded shadow-lg">
+              <div className="font-semibold mb-1">Playback error</div>
+              <div className="break-words">{song.playbackError}</div>
+            </div>
+          )}
+        </div>
       </div>
       
       <div className="flex-grow min-w-0">