diff --git a/toju-app/src/app/domains/chat/README.md b/toju-app/src/app/domains/chat/README.md
index 1d1d413..0f1f7e4 100644
--- a/toju-app/src/app/domains/chat/README.md
+++ b/toju-app/src/app/domains/chat/README.md
@@ -7,11 +7,14 @@ Text messaging, reactions, GIF search, typing indicators, and the user list. All
 ```
 chat/
 ├── application/
-│   └── klipy.service.ts                     GIF search via the KLIPY API (proxied through the server)
+│   └── services/
+│       ├── klipy.service.ts                     GIF search via the KLIPY API (proxied through the server)
+│       └── link-metadata.service.ts             Link preview metadata fetching
 │
 ├── domain/
-│   ├── message.rules.ts                     canEditMessage, normaliseDeletedMessage, getMessageTimestamp
-│   └── message-sync.rules.ts               Inventory-based sync: chunkArray, findMissingIds, limits
+│   └── rules/
+│       ├── message.rules.ts                     canEditMessage, normaliseDeletedMessage, getMessageTimestamp
+│       └── message-sync.rules.ts               Inventory-based sync: chunkArray, findMissingIds, limits
 │
 ├── feature/
 │   ├── chat-messages/                       Main chat view (orchestrates composer, list, overlays)
@@ -25,6 +28,7 @@ chat/
 │   │   └── services/
 │   │       └── chat-markdown.service.ts           Markdown-to-HTML rendering
 │   │
+│   ├── chat-image-proxy-fallback.directive.ts  Image proxy fallback for broken URLs
 │   ├── klipy-gif-picker/                    GIF search/browse picker panel
 │   ├── typing-indicator/                    "X is typing..." display (3 s TTL, max 4 names)
 │   └── user-list/                           Online user sidebar
@@ -129,7 +133,7 @@ graph LR
     Klipy --> API
 
     click Picker "feature/klipy-gif-picker/" "GIF search panel" _blank
-    click Klipy "application/klipy.service.ts" "GIF search via KLIPY API" _blank
+    click Klipy "application/services/klipy.service.ts" "GIF search via KLIPY API" _blank
     click SD "../server-directory/application/server-directory.facade.ts" "Resolves API base URL" _blank
 ```
 
diff --git a/toju-app/src/app/domains/chat/application/klipy.service.ts b/toju-app/src/app/domains/chat/application/services/klipy.service.ts
similarity index 98%
rename from toju-app/src/app/domains/chat/application/klipy.service.ts
rename to toju-app/src/app/domains/chat/application/services/klipy.service.ts
index e789d53..bca817f 100644
--- a/toju-app/src/app/domains/chat/application/klipy.service.ts
+++ b/toju-app/src/app/domains/chat/application/services/klipy.service.ts
@@ -13,7 +13,7 @@ import {
   throwError
 } from 'rxjs';
 import { catchError, map } from 'rxjs/operators';
-import { ServerDirectoryFacade } from '../../server-directory';
+import { ServerDirectoryFacade } from '../../../server-directory';
 
 export interface KlipyGif {
   id: string;
diff --git a/toju-app/src/app/domains/chat/application/link-metadata.service.ts b/toju-app/src/app/domains/chat/application/services/link-metadata.service.ts
similarity index 89%
rename from toju-app/src/app/domains/chat/application/link-metadata.service.ts
rename to toju-app/src/app/domains/chat/application/services/link-metadata.service.ts
index f8fab23..4970373 100644
--- a/toju-app/src/app/domains/chat/application/link-metadata.service.ts
+++ b/toju-app/src/app/domains/chat/application/services/link-metadata.service.ts
@@ -1,8 +1,8 @@
 import { Injectable, inject } from '@angular/core';
 import { HttpClient } from '@angular/common/http';
 import { firstValueFrom } from 'rxjs';
-import { ServerDirectoryFacade } from '../../server-directory';
-import { LinkMetadata } from '../../../shared-kernel';
+import { ServerDirectoryFacade } from '../../../server-directory';
+import { LinkMetadata } from '../../../../shared-kernel';
 
 const URL_PATTERN = /https?:\/\/[^\s<>)"']+/g;
 
diff --git a/toju-app/src/app/domains/chat/domain/message-sync.rules.ts b/toju-app/src/app/domains/chat/domain/rules/message-sync.rules.ts
similarity index 100%
rename from toju-app/src/app/domains/chat/domain/message-sync.rules.ts
rename to toju-app/src/app/domains/chat/domain/rules/message-sync.rules.ts
diff --git a/toju-app/src/app/domains/chat/domain/message.rules.ts b/toju-app/src/app/domains/chat/domain/rules/message.rules.ts
similarity index 98%
rename from toju-app/src/app/domains/chat/domain/message.rules.ts
rename to toju-app/src/app/domains/chat/domain/rules/message.rules.ts
index f85b811..feeb5ca 100644
--- a/toju-app/src/app/domains/chat/domain/message.rules.ts
+++ b/toju-app/src/app/domains/chat/domain/rules/message.rules.ts
@@ -1,4 +1,4 @@
-import { DELETED_MESSAGE_CONTENT, type Message } from '../../../shared-kernel';
+import { DELETED_MESSAGE_CONTENT, type Message } from '../../../../shared-kernel';
 
 /** Extracts the effective timestamp from a message (editedAt takes priority). */
 export function getMessageTimestamp(msg: Message): number {
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
index d73a818..8793ce8 100644
--- 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
@@ -7,7 +7,7 @@ import {
   input,
   signal
 } from '@angular/core';
-import { KlipyService } from '../application/klipy.service';
+import { KlipyService } from '../application/services/klipy.service';
 
 @Directive({
   selector: 'img[appChatImageProxyFallback]',
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/chat-messages.component.ts b/toju-app/src/app/domains/chat/feature/chat-messages/chat-messages.component.ts
index 462f515..ec369b1 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/chat-messages.component.ts
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/chat-messages.component.ts
@@ -11,7 +11,7 @@ import { Store } from '@ngrx/store';
 import { ElectronBridgeService } from '../../../../core/platform/electron/electron-bridge.service';
 import { RealtimeSessionFacade } from '../../../../core/realtime';
 import { Attachment, AttachmentFacade } from '../../../attachment';
-import { KlipyGif } from '../../application/klipy.service';
+import { KlipyGif } from '../../application/services/klipy.service';
 import { MessagesActions } from '../../../../store/messages/messages.actions';
 import {
   selectAllMessages,
@@ -33,7 +33,7 @@ import {
   ChatMessageImageContextMenuEvent,
   ChatMessageReactionEvent,
   ChatMessageReplyEvent
-} from './models/chat-messages.models';
+} from './models/chat-messages.model';
 
 @Component({
   selector: 'app-chat-messages',
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 008e334..fab1f8a 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
@@ -21,12 +21,12 @@ import {
 } from '@ng-icons/lucide';
 import type { ClipboardFilePayload } from '../../../../../../core/platform/electron/electron-api.models';
 import { ElectronBridgeService } from '../../../../../../core/platform/electron/electron-bridge.service';
-import { KlipyGif, KlipyService } from '../../../../application/klipy.service';
+import { KlipyGif, KlipyService } from '../../../../application/services/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';
+import { ChatMessageComposerSubmitEvent } from '../../models/chat-messages.model';
 
 type LocalFileWithPath = File & {
   path?: string;
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 846382d..d6296ec 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
@@ -29,7 +29,7 @@ import {
   AttachmentFacade,
   MAX_AUTO_SAVE_SIZE_BYTES
 } from '../../../../../attachment';
-import { KlipyService } from '../../../../application/klipy.service';
+import { KlipyService } from '../../../../application/services/klipy.service';
 import { DELETED_MESSAGE_CONTENT, Message } from '../../../../../../shared-kernel';
 import {
   ChatAudioPlayerComponent,
@@ -45,7 +45,7 @@ import {
   ChatMessageImageContextMenuEvent,
   ChatMessageReactionEvent,
   ChatMessageReplyEvent
-} from '../../models/chat-messages.models';
+} from '../../models/chat-messages.model';
 
 const COMMON_EMOJIS = [
   '👍',
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-list/chat-message-list.component.ts b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-list/chat-message-list.component.ts
index cfd7368..bc0b614 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-list/chat-message-list.component.ts
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-list/chat-message-list.component.ts
@@ -13,7 +13,7 @@ import {
   signal
 } from '@angular/core';
 import { Attachment } from '../../../../../attachment';
-import { getMessageTimestamp } from '../../../../domain/message.rules';
+import { getMessageTimestamp } from '../../../../domain/rules/message.rules';
 import { Message } from '../../../../../../shared-kernel';
 import {
   ChatMessageDeleteEvent,
@@ -22,7 +22,7 @@ import {
   ChatMessageImageContextMenuEvent,
   ChatMessageReactionEvent,
   ChatMessageReplyEvent
-} from '../../models/chat-messages.models';
+} from '../../models/chat-messages.model';
 import { ChatMessageItemComponent } from '../message-item/chat-message-item.component';
 
 interface PrismGlobal {
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-overlays/chat-message-overlays.component.ts b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-overlays/chat-message-overlays.component.ts
index 70e1d41..1563ed6 100644
--- a/toju-app/src/app/domains/chat/feature/chat-messages/components/message-overlays/chat-message-overlays.component.ts
+++ b/toju-app/src/app/domains/chat/feature/chat-messages/components/message-overlays/chat-message-overlays.component.ts
@@ -12,7 +12,7 @@ import {
 } from '@ng-icons/lucide';
 import { Attachment } from '../../../../../attachment';
 import { ContextMenuComponent } from '../../../../../../shared';
-import { ChatMessageImageContextMenuEvent } from '../../models/chat-messages.models';
+import { ChatMessageImageContextMenuEvent } from '../../models/chat-messages.model';
 
 @Component({
   selector: 'app-chat-message-overlays',
diff --git a/toju-app/src/app/domains/chat/feature/chat-messages/models/chat-messages.models.ts b/toju-app/src/app/domains/chat/feature/chat-messages/models/chat-messages.model.ts
similarity index 100%
rename from toju-app/src/app/domains/chat/feature/chat-messages/models/chat-messages.models.ts
rename to toju-app/src/app/domains/chat/feature/chat-messages/models/chat-messages.model.ts
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 3529d80..67a7bab 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
@@ -20,7 +20,7 @@ import {
   lucideSearch,
   lucideX
 } from '@ng-icons/lucide';
-import { KlipyGif, KlipyService } from '../../application/klipy.service';
+import { KlipyGif, KlipyService } from '../../application/services/klipy.service';
 import { ChatImageProxyFallbackDirective } from '../chat-image-proxy-fallback.directive';
 
 const KLIPY_CARD_MIN_WIDTH = 140;
diff --git a/toju-app/src/app/domains/chat/index.ts b/toju-app/src/app/domains/chat/index.ts
index 804330b..7f6d8e6 100644
--- a/toju-app/src/app/domains/chat/index.ts
+++ b/toju-app/src/app/domains/chat/index.ts
@@ -1,6 +1,7 @@
-export * from './application/klipy.service';
-export * from './domain/message.rules';
-export * from './domain/message-sync.rules';
+export * from './application/services/klipy.service';
+export * from './application/services/link-metadata.service';
+export * from './domain/rules/message.rules';
+export * from './domain/rules/message-sync.rules';
 export { ChatMessagesComponent } from './feature/chat-messages/chat-messages.component';
 export { TypingIndicatorComponent } from './feature/typing-indicator/typing-indicator.component';
 export { KlipyGifPickerComponent } from './feature/klipy-gif-picker/klipy-gif-picker.component';
diff --git a/toju-app/src/app/store/messages/messages.effects.ts b/toju-app/src/app/store/messages/messages.effects.ts
index d3a7318..785e480 100644
--- a/toju-app/src/app/store/messages/messages.effects.ts
+++ b/toju-app/src/app/store/messages/messages.effects.ts
@@ -37,7 +37,7 @@ import { DatabaseService } from '../../infrastructure/persistence';
 import { reportDebuggingError, trackDebuggingTaskFailure } from '../../core/helpers/debugging-helpers';
 import { DebuggingService } from '../../core/services';
 import { AttachmentFacade } from '../../domains/attachment';
-import { LinkMetadataService } from '../../domains/chat/application/link-metadata.service';
+import { LinkMetadataService } from '../../domains/chat/application/services/link-metadata.service';
 import { TimeSyncService } from '../../core/services/time-sync.service';
 import {
   DELETED_MESSAGE_CONTENT,
@@ -45,7 +45,7 @@ import {
   Reaction
 } from '../../shared-kernel';
 import { hydrateMessages } from './messages.helpers';
-import { canEditMessage } from '../../domains/chat/domain/message.rules';
+import { canEditMessage } from '../../domains/chat/domain/rules/message.rules';
 import { resolveRoomPermission } from '../../domains/access-control';
 import { dispatchIncomingMessage, IncomingMessageContext } from './messages-incoming.handlers';
 
diff --git a/toju-app/src/app/store/messages/messages.helpers.ts b/toju-app/src/app/store/messages/messages.helpers.ts
index 68747dc..4a3fc2b 100644
--- a/toju-app/src/app/store/messages/messages.helpers.ts
+++ b/toju-app/src/app/store/messages/messages.helpers.ts
@@ -4,8 +4,8 @@
  */
 import { Message } from '../../shared-kernel';
 import { DatabaseService } from '../../infrastructure/persistence';
-import { getMessageTimestamp, normaliseDeletedMessage } from '../../domains/chat/domain/message.rules';
-import type { InventoryItem } from '../../domains/chat/domain/message-sync.rules';
+import { getMessageTimestamp, normaliseDeletedMessage } from '../../domains/chat/domain/rules/message.rules';
+import type { InventoryItem } from '../../domains/chat/domain/rules/message-sync.rules';
 
 // Re-export domain logic so existing callers keep working
 export {
@@ -13,7 +13,7 @@ export {
   getLatestTimestamp,
   normaliseDeletedMessage,
   canEditMessage
-} from '../../domains/chat/domain/message.rules';
+} from '../../domains/chat/domain/rules/message.rules';
 export {
   INVENTORY_LIMIT,
   CHUNK_SIZE,
@@ -23,8 +23,8 @@ export {
   FULL_SYNC_LIMIT,
   chunkArray,
   findMissingIds
-} from '../../domains/chat/domain/message-sync.rules';
-export type { InventoryItem } from '../../domains/chat/domain/message-sync.rules';
+} from '../../domains/chat/domain/rules/message-sync.rules';
+export type { InventoryItem } from '../../domains/chat/domain/rules/message-sync.rules';
 
 /** Hydrates a single message with its reactions from the database. */
 export async function hydrateMessage(