diff --git a/toju-app/src/app/domains/chat/README.md b/toju-app/src/app/domains/chat/README.md
index c8f7d9c..e8d7c3e 100644
--- a/toju-app/src/app/domains/chat/README.md
+++ b/toju-app/src/app/domains/chat/README.md
@@ -109,7 +109,7 @@ sequenceDiagram
 
 ## GIF integration
 
-`KlipyService` checks availability on the active server, then proxies search requests through the server API. Images are rendered via an image proxy endpoint to avoid mixed-content issues.
+`KlipyService` checks availability on the active server, then proxies search requests through the server API. Rendered remote images now attempt a direct load first and only fall back to the image proxy after the browser reports a load failure, which is the practical approximation of a CORS or mixed-content fallback path in the renderer.
 
 ```mermaid
 graph LR
diff --git a/toju-app/src/app/domains/chat/application/klipy.service.ts b/toju-app/src/app/domains/chat/application/klipy.service.ts
index 4dfcfc5..e789d53 100644
--- a/toju-app/src/app/domains/chat/application/klipy.service.ts
+++ b/toju-app/src/app/domains/chat/application/klipy.service.ts
@@ -135,6 +135,10 @@ export class KlipyService {
   }
 
   buildRenderableImageUrl(url: string): string {
+    return this.normalizeMediaUrl(url);
+  }
+
+  buildImageProxyUrl(url: string): string {
     const trimmed = this.normalizeMediaUrl(url);
 
     if (!trimmed)
diff --git a/toju-app/src/app/domains/chat/feature/chat-image-proxy-fallback.directive.ts b/toju-app/src/app/domains/chat/feature/chat-image-proxy-fallback.directive.ts
new file mode 100644
index 0000000..d73a818
--- /dev/null
+++ b/toju-app/src/app/domains/chat/feature/chat-image-proxy-fallback.directive.ts
@@ -0,0 +1,50 @@
+import {
+  Directive,
+  HostBinding,
+  HostListener,
+  effect,
+  inject,
+  input,
+  signal
+} from '@angular/core';
+import { KlipyService } from '../application/klipy.service';
+
+@Directive({
+  selector: 'img[appChatImageProxyFallback]',
+  standalone: true
+})
+export class ChatImageProxyFallbackDirective {
+  readonly sourceUrl = input('', { alias: 'appChatImageProxyFallback' });
+
+  private readonly klipy = inject(KlipyService);
+  private readonly renderedSource = signal('');
+  private hasAppliedProxyFallback = false;
+
+  constructor() {
+    effect(() => {
+      this.hasAppliedProxyFallback = false;
+      this.renderedSource.set(this.klipy.buildRenderableImageUrl(this.sourceUrl()));
+    });
+  }
+
+  @HostBinding('src')
+  get src(): string {
+    return this.renderedSource();
+  }
+
+  @HostListener('error')
+  handleError(): void {
+    if (this.hasAppliedProxyFallback) {
+      return;
+    }
+
+    const proxyUrl = this.klipy.buildImageProxyUrl(this.sourceUrl());
+
+    if (!proxyUrl || proxyUrl === this.renderedSource()) {
+      return;
+    }
+
+    this.hasAppliedProxyFallback = true;
+    this.renderedSource.set(proxyUrl);
+  }
+}
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.html b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.html
index e298628..ce800e2 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.html
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.html
@@ -206,7 +206,7 @@
           <div class="group flex max-w-sm items-center gap-3 rounded-xl border border-border bg-secondary/60 px-2.5 py-2">
             <div class="relative h-12 w-12 overflow-hidden rounded-lg bg-secondary/80">
               <img
-                [src]="getPendingKlipyGifPreviewUrl()"
+                [appChatImageProxyFallback]="pendingKlipyGif()!.previewUrl || pendingKlipyGif()!.url"
                 [alt]="pendingKlipyGif()!.title || 'KLIPY GIF'"
                 class="h-full w-full object-cover"
                 loading="lazy"
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.ts b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.ts
index 6ce6069..008e334 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.ts
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-composer/chat-message-composer.component.ts
@@ -23,6 +23,7 @@ import type { ClipboardFilePayload } from '../../../../../../core/platform/elect
 import { ElectronBridgeService } from '../../../../../../core/platform/electron/electron-bridge.service';
 import { KlipyGif, KlipyService } from '../../../../application/klipy.service';
 import { Message } from '../../../../../../shared-kernel';
+import { ChatImageProxyFallbackDirective } from '../../../chat-image-proxy-fallback.directive';
 import { TypingIndicatorComponent } from '../../../typing-indicator/typing-indicator.component';
 import { ChatMarkdownService } from '../../services/chat-markdown.service';
 import { ChatMessageComposerSubmitEvent } from '../../models/chat-messages.models';
@@ -40,6 +41,7 @@ const DEFAULT_TEXTAREA_HEIGHT = 62;
     CommonModule,
     FormsModule,
     NgIcon,
+    ChatImageProxyFallbackDirective,
     TypingIndicatorComponent
   ],
   viewProviders: [
@@ -231,12 +233,6 @@ export class ChatMessageComposerComponent implements AfterViewInit, OnDestroy {
     requestAnimationFrame(() => this.messageInputRef?.nativeElement.focus());
   }
 
-  getPendingKlipyGifPreviewUrl(): string {
-    const gif = this.pendingKlipyGif();
-
-    return gif ? this.klipy.buildRenderableImageUrl(gif.previewUrl || gif.url) : '';
-  }
-
   formatBytes(bytes: number): string {
     const units = [
       'B',
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.html b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.html
index 67f24ef..e1cd57a 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.html
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.html
@@ -98,7 +98,7 @@
             >
               <div class="relative mt-2 inline-block overflow-hidden rounded-md border border-border/60 bg-secondary/20">
                 <img
-                  [src]="getMarkdownImageSource(node.url)"
+                  [appChatImageProxyFallback]="node.url"
                   [alt]="node.alt || 'Shared image'"
                   class="block max-h-80 max-w-full w-auto"
                   loading="lazy"
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.ts b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.ts
index a02c42b..429858c 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.ts
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-item/chat-message-item.component.ts
@@ -41,6 +41,7 @@ import {
   ChatVideoPlayerComponent,
   UserAvatarComponent
 } from '../../../../../../shared';
+import { ChatImageProxyFallbackDirective } from '../../../chat-image-proxy-fallback.directive';
 import {
   ChatMessageDeleteEvent,
   ChatMessageEditEvent,
@@ -102,6 +103,7 @@ interface ChatMessageAttachmentViewModel extends Attachment {
     ChatVideoPlayerComponent,
     RemarkModule,
     MermaidComponent,
+    ChatImageProxyFallbackDirective,
     UserAvatarComponent
   ],
   viewProviders: [
@@ -318,10 +320,6 @@ export class ChatMessageItemComponent {
     );
   }
 
-  getMarkdownImageSource(url?: string): string {
-    return url ? this.klipy.buildRenderableImageUrl(url) : '';
-  }
-
   getMermaidCode(code?: string): string {
     return (code ?? '').replace(MERMAID_LINE_BREAK_PATTERN, '\n').trim();
   }
diff --git a/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.html b/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.html
index 977be48..918ed17 100644
--- a/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.html
+++ b/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.html
@@ -93,7 +93,7 @@
               [style.aspect-ratio]="gifAspectRatio(gif)"
             >
               <img
-                [src]="gifPreviewUrl(gif)"
+                [appChatImageProxyFallback]="gif.previewUrl || gif.url"
                 [alt]="gif.title || 'KLIPY GIF'"
                 class="h-full w-full object-cover transition-transform duration-200 group-hover:scale-[1.03]"
                 loading="lazy"
diff --git a/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.ts b/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.ts
index cec42a2..06d7b99 100644
--- a/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.ts
+++ b/toju-app/src/app/domains/chat/feature/klipy-gif-picker/klipy-gif-picker.component.ts
@@ -21,6 +21,7 @@ import {
   lucideX
 } from '@ng-icons/lucide';
 import { KlipyGif, KlipyService } from '../../application/klipy.service';
+import { ChatImageProxyFallbackDirective } from '../chat-image-proxy-fallback.directive';
 
 @Component({
   selector: 'app-klipy-gif-picker',
@@ -28,7 +29,8 @@ import { KlipyGif, KlipyService } from '../../application/klipy.service';
   imports: [
     CommonModule,
     FormsModule,
-    NgIcon
+    NgIcon,
+    ChatImageProxyFallbackDirective
   ],
   viewProviders: [
     provideIcons({
@@ -112,10 +114,6 @@ export class KlipyGifPickerComponent implements OnInit, AfterViewInit, OnDestroy
     return '1 / 1';
   }
 
-  gifPreviewUrl(gif: KlipyGif): string {
-    return this.klipy.buildRenderableImageUrl(gif.previewUrl || gif.url);
-  }
-
   private async loadResults(reset: boolean): Promise<void> {
     if (reset) {
       this.currentPage = 1;