diff --git a/tools/server/public/index.html.gz b/tools/server/public/index.html.gz
index d0c44534efcb6..f1a7568d7c674 100644
Binary files a/tools/server/public/index.html.gz and b/tools/server/public/index.html.gz differ
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte b/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
index 666febf0d28d6..374eb05ab0f46 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
@@ -7,6 +7,7 @@
 		ChatMessages,
 		ChatProcessingInfo,
 		EmptyFileAlertDialog,
+		ChatErrorDialog,
 		ServerErrorSplash,
 		ServerInfo,
 		ServerLoadingSplash,
@@ -22,10 +23,11 @@
 		activeMessages,
 		activeConversation,
 		deleteConversation,
+		dismissErrorDialog,
+		errorDialog,
 		isLoading,
 		sendMessage,
-		stopGeneration,
-		setMaxContextError
+		stopGeneration
 	} from '$lib/stores/chat.svelte';
 	import {
 		supportsVision,
@@ -34,7 +36,6 @@
 		serverWarning,
 		serverStore
 	} from '$lib/stores/server.svelte';
-	import { contextService } from '$lib/services';
 	import { parseFilesToMessageExtras } from '$lib/utils/convert-files-to-extra';
 	import { isFileTypeSupported } from '$lib/utils/file-type';
 	import { filterFilesByModalities } from '$lib/utils/modality-file-validation';
@@ -79,6 +80,7 @@
 		showCenteredEmpty && !activeConversation() && activeMessages().length === 0 && !isLoading()
 	);
 
+	let activeErrorDialog = $derived(errorDialog());
 	let isServerLoading = $derived(serverLoading());
 
 	async function handleDeleteConfirm() {
@@ -105,6 +107,12 @@
 		}
 	}
 
+	function handleErrorDialogOpenChange(open: boolean) {
+		if (!open) {
+			dismissErrorDialog();
+		}
+	}
+
 	function handleDragOver(event: DragEvent) {
 		event.preventDefault();
 	}
@@ -183,21 +191,6 @@
 
 		const extras = result?.extras;
 
-		// Check context limit using real-time slots data
-		const contextCheck = await contextService.checkContextLimit();
-
-		if (contextCheck && contextCheck.wouldExceed) {
-			const errorMessage = contextService.getContextErrorMessage(contextCheck);
-
-			setMaxContextError({
-				message: errorMessage,
-				estimatedTokens: contextCheck.currentUsage,
-				maxContext: contextCheck.maxContext
-			});
-
-			return false;
-		}
-
 		// Enable autoscroll for user-initiated message sending
 		userScrolledUp = false;
 		autoScrollEnabled = true;
@@ -461,6 +454,13 @@
 	}}
 />
 
+<ChatErrorDialog
+	message={activeErrorDialog?.message ?? ''}
+	onOpenChange={handleErrorDialogOpenChange}
+	open={Boolean(activeErrorDialog)}
+	type={activeErrorDialog?.type ?? 'server'}
+/>
+
 <style>
 	.conversation-chat-form {
 		position: relative;
diff --git a/tools/server/webui/src/lib/components/app/dialogs/ChatErrorDialog.svelte b/tools/server/webui/src/lib/components/app/dialogs/ChatErrorDialog.svelte
new file mode 100644
index 0000000000000..8ecb58905a638
--- /dev/null
+++ b/tools/server/webui/src/lib/components/app/dialogs/ChatErrorDialog.svelte
@@ -0,0 +1,60 @@
+<script lang="ts">
+	import * as AlertDialog from '$lib/components/ui/alert-dialog';
+	import { AlertTriangle, TimerOff } from '@lucide/svelte';
+
+	interface Props {
+		open: boolean;
+		type: 'timeout' | 'server';
+		message: string;
+		onOpenChange?: (open: boolean) => void;
+	}
+
+	let { open = $bindable(), type, message, onOpenChange }: Props = $props();
+
+	const isTimeout = $derived(type === 'timeout');
+	const title = $derived(isTimeout ? 'TCP Timeout' : 'Server Error');
+	const description = $derived(
+		isTimeout
+			? 'The request did not receive a response from the server before timing out.'
+			: 'The server responded with an error message. Review the details below.'
+	);
+	const iconClass = $derived(isTimeout ? 'text-destructive' : 'text-amber-500');
+	const badgeClass = $derived(
+		isTimeout
+			? 'border-destructive/40 bg-destructive/10 text-destructive'
+			: 'border-amber-500/40 bg-amber-500/10 text-amber-600 dark:text-amber-400'
+	);
+
+	function handleOpenChange(newOpen: boolean) {
+		open = newOpen;
+		onOpenChange?.(newOpen);
+	}
+</script>
+
+<AlertDialog.Root {open} onOpenChange={handleOpenChange}>
+	<AlertDialog.Content>
+		<AlertDialog.Header>
+			<AlertDialog.Title class="flex items-center gap-2">
+				{#if isTimeout}
+					<TimerOff class={`h-5 w-5 ${iconClass}`} />
+				{:else}
+					<AlertTriangle class={`h-5 w-5 ${iconClass}`} />
+				{/if}
+
+				{title}
+			</AlertDialog.Title>
+
+			<AlertDialog.Description>
+				{description}
+			</AlertDialog.Description>
+		</AlertDialog.Header>
+
+		<div class={`rounded-lg border px-4 py-3 text-sm ${badgeClass}`}>
+			<p class="font-medium">{message}</p>
+		</div>
+
+		<AlertDialog.Footer>
+			<AlertDialog.Action onclick={() => handleOpenChange(false)}>Close</AlertDialog.Action>
+		</AlertDialog.Footer>
+	</AlertDialog.Content>
+</AlertDialog.Root>
diff --git a/tools/server/webui/src/lib/components/app/dialogs/MaximumContextAlertDialog.svelte b/tools/server/webui/src/lib/components/app/dialogs/MaximumContextAlertDialog.svelte
deleted file mode 100644
index cea0f631a2b98..0000000000000
--- a/tools/server/webui/src/lib/components/app/dialogs/MaximumContextAlertDialog.svelte
+++ /dev/null
@@ -1,66 +0,0 @@
-<script lang="ts">
-	import { AlertTriangle } from '@lucide/svelte';
-	import * as AlertDialog from '$lib/components/ui/alert-dialog';
-	import { maxContextError, clearMaxContextError } from '$lib/stores/chat.svelte';
-</script>
-
-<AlertDialog.Root
-	open={maxContextError() !== null}
-	onOpenChange={(open) => !open && clearMaxContextError()}
->
-	<AlertDialog.Content>
-		<AlertDialog.Header>
-			<AlertDialog.Title class="flex items-center gap-2">
-				<AlertTriangle class="h-5 w-5 text-destructive" />
-
-				Message Too Long
-			</AlertDialog.Title>
-
-			<AlertDialog.Description>
-				Your message exceeds the model's context window and cannot be processed.
-			</AlertDialog.Description>
-		</AlertDialog.Header>
-
-		{#if maxContextError()}
-			<div class="space-y-3 text-sm">
-				<div class="rounded-lg bg-muted p-3">
-					<div class="mb-2 font-medium">Token Usage:</div>
-
-					<div class="space-y-1 text-muted-foreground">
-						<div>
-							Estimated tokens:
-
-							<span class="font-mono">
-								{maxContextError()?.estimatedTokens.toLocaleString()}
-							</span>
-						</div>
-
-						<div>
-							Context window:
-
-							<span class="font-mono">
-								{maxContextError()?.maxContext.toLocaleString()}
-							</span>
-						</div>
-					</div>
-				</div>
-
-				<div>
-					<div class="mb-2 font-medium">Suggestions:</div>
-
-					<ul class="list-inside list-disc space-y-1 text-muted-foreground">
-						<li>Shorten your message</li>
-
-						<li>Remove some file attachments</li>
-
-						<li>Start a new conversation</li>
-					</ul>
-				</div>
-			</div>
-		{/if}
-
-		<AlertDialog.Footer>
-			<AlertDialog.Action onclick={() => clearMaxContextError()}>Got it</AlertDialog.Action>
-		</AlertDialog.Footer>
-	</AlertDialog.Content>
-</AlertDialog.Root>
diff --git a/tools/server/webui/src/lib/components/app/index.ts b/tools/server/webui/src/lib/components/app/index.ts
index 7c1af27ecd3fd..63a99f4343320 100644
--- a/tools/server/webui/src/lib/components/app/index.ts
+++ b/tools/server/webui/src/lib/components/app/index.ts
@@ -30,12 +30,11 @@ export { default as ChatSidebar } from './chat/ChatSidebar/ChatSidebar.svelte';
 export { default as ChatSidebarConversationItem } from './chat/ChatSidebar/ChatSidebarConversationItem.svelte';
 export { default as ChatSidebarSearch } from './chat/ChatSidebar/ChatSidebarSearch.svelte';
 
+export { default as ChatErrorDialog } from './dialogs/ChatErrorDialog.svelte';
 export { default as EmptyFileAlertDialog } from './dialogs/EmptyFileAlertDialog.svelte';
 
 export { default as ConversationTitleUpdateDialog } from './dialogs/ConversationTitleUpdateDialog.svelte';
 
-export { default as MaximumContextAlertDialog } from './dialogs/MaximumContextAlertDialog.svelte';
-
 export { default as KeyboardShortcutInfo } from './misc/KeyboardShortcutInfo.svelte';
 
 export { default as MarkdownContent } from './misc/MarkdownContent.svelte';
diff --git a/tools/server/webui/src/lib/services/chat.ts b/tools/server/webui/src/lib/services/chat.ts
index 8d9dcf75801c6..37e60b85b5a6a 100644
--- a/tools/server/webui/src/lib/services/chat.ts
+++ b/tools/server/webui/src/lib/services/chat.ts
@@ -13,7 +13,7 @@ import { slotsService } from './slots';
  *   - Manages streaming and non-streaming response parsing
  *   - Provides request abortion capabilities
  *   - Converts database messages to API format
- *   - Handles error translation and context detection
+ *   - Handles error translation for server responses
  *
  * - **ChatStore**: Stateful orchestration and UI state management
  *   - Uses ChatService for all AI model communication
@@ -26,7 +26,6 @@ import { slotsService } from './slots';
  * - Streaming response handling with real-time callbacks
  * - Reasoning content extraction and processing
  * - File attachment processing (images, PDFs, audio, text)
- * - Context error detection and reporting
  * - Request lifecycle management (abort, cleanup)
  */
 export class ChatService {
@@ -209,10 +208,13 @@ export class ChatService {
 					userFriendlyError = new Error(
 						'Unable to connect to server - please check if the server is running'
 					);
+					userFriendlyError.name = 'NetworkError';
 				} else if (error.message.includes('ECONNREFUSED')) {
 					userFriendlyError = new Error('Connection refused - server may be offline');
+					userFriendlyError.name = 'NetworkError';
 				} else if (error.message.includes('ETIMEDOUT')) {
-					userFriendlyError = new Error('Request timeout - server may be overloaded');
+					userFriendlyError = new Error('Request timed out - the server took too long to respond');
+					userFriendlyError.name = 'TimeoutError';
 				} else {
 					userFriendlyError = error;
 				}
@@ -262,6 +264,7 @@ export class ChatService {
 		let fullReasoningContent = '';
 		let hasReceivedData = false;
 		let lastTimings: ChatMessageTimings | undefined;
+		let streamFinished = false;
 
 		try {
 			let chunk = '';
@@ -277,18 +280,8 @@ export class ChatService {
 					if (line.startsWith('data: ')) {
 						const data = line.slice(6);
 						if (data === '[DONE]') {
-							if (!hasReceivedData && aggregatedContent.length === 0) {
-								const contextError = new Error(
-									'The request exceeds the available context size. Try increasing the context size or enable context shift.'
-								);
-								contextError.name = 'ContextError';
-								onError?.(contextError);
-								return;
-							}
-
-							onComplete?.(aggregatedContent, fullReasoningContent || undefined, lastTimings);
-
-							return;
+							streamFinished = true;
+							continue;
 						}
 
 						try {
@@ -326,13 +319,13 @@ export class ChatService {
 				}
 			}
 
-			if (!hasReceivedData && aggregatedContent.length === 0) {
-				const contextError = new Error(
-					'The request exceeds the available context size. Try increasing the context size or enable context shift.'
-				);
-				contextError.name = 'ContextError';
-				onError?.(contextError);
-				return;
+			if (streamFinished) {
+				if (!hasReceivedData && aggregatedContent.length === 0) {
+					const noResponseError = new Error('No response received from server. Please try again.');
+					throw noResponseError;
+				}
+
+				onComplete?.(aggregatedContent, fullReasoningContent || undefined, lastTimings);
 			}
 		} catch (error) {
 			const err = error instanceof Error ? error : new Error('Stream error');
@@ -368,12 +361,8 @@ export class ChatService {
 			const responseText = await response.text();
 
 			if (!responseText.trim()) {
-				const contextError = new Error(
-					'The request exceeds the available context size. Try increasing the context size or enable context shift.'
-				);
-				contextError.name = 'ContextError';
-				onError?.(contextError);
-				throw contextError;
+				const noResponseError = new Error('No response received from server. Please try again.');
+				throw noResponseError;
 			}
 
 			const data: ApiChatCompletionResponse = JSON.parse(responseText);
@@ -385,22 +374,14 @@ export class ChatService {
 			}
 
 			if (!content.trim()) {
-				const contextError = new Error(
-					'The request exceeds the available context size. Try increasing the context size or enable context shift.'
-				);
-				contextError.name = 'ContextError';
-				onError?.(contextError);
-				throw contextError;
+				const noResponseError = new Error('No response received from server. Please try again.');
+				throw noResponseError;
 			}
 
 			onComplete?.(content, reasoningContent);
 
 			return content;
 		} catch (error) {
-			if (error instanceof Error && error.name === 'ContextError') {
-				throw error;
-			}
-
 			const err = error instanceof Error ? error : new Error('Parse error');
 
 			onError?.(err);
@@ -594,37 +575,19 @@ export class ChatService {
 			const errorText = await response.text();
 			const errorData: ApiErrorResponse = JSON.parse(errorText);
 
-			if (errorData.error?.type === 'exceed_context_size_error') {
-				const contextError = errorData.error as ApiContextSizeError;
-				const error = new Error(contextError.message);
-				error.name = 'ContextError';
-				// Attach structured context information
-				(
-					error as Error & {
-						contextInfo?: { promptTokens: number; maxContext: number; estimatedTokens: number };
-					}
-				).contextInfo = {
-					promptTokens: contextError.n_prompt_tokens,
-					maxContext: contextError.n_ctx,
-					estimatedTokens: contextError.n_prompt_tokens
-				};
-				return error;
-			}
-
-			// Fallback for other error types
 			const message = errorData.error?.message || 'Unknown server error';
-			return new Error(message);
+			const error = new Error(message);
+			error.name = response.status === 400 ? 'ServerError' : 'HttpError';
+
+			return error;
 		} catch {
 			// If we can't parse the error response, return a generic error
-			return new Error(`Server error (${response.status}): ${response.statusText}`);
+			const fallback = new Error(`Server error (${response.status}): ${response.statusText}`);
+			fallback.name = 'HttpError';
+			return fallback;
 		}
 	}
 
-	/**
-	 * Updates the processing state with timing information from the server response
-	 * @param timings - Timing data from the API response
-	 * @param promptProgress - Progress data from the API response
-	 */
 	private updateProcessingState(
 		timings?: ChatMessageTimings,
 		promptProgress?: ChatMessagePromptProgress
diff --git a/tools/server/webui/src/lib/services/context.ts b/tools/server/webui/src/lib/services/context.ts
deleted file mode 100644
index d4af7508e7c75..0000000000000
--- a/tools/server/webui/src/lib/services/context.ts
+++ /dev/null
@@ -1,102 +0,0 @@
-import { slotsService } from './slots';
-
-export interface ContextCheckResult {
-	wouldExceed: boolean;
-	currentUsage: number;
-	maxContext: number;
-	availableTokens: number;
-	reservedTokens: number;
-}
-
-/**
- * ContextService - Context window management and limit checking
- *
- * This service provides context window monitoring and limit checking using real-time
- * server data from the slots service. It helps prevent context overflow by tracking
- * current usage and calculating available space for new content.
- *
- * **Architecture & Relationships:**
- * - **ContextService** (this class): Context limit monitoring
- *   - Uses SlotsService for real-time context usage data
- *   - Calculates available tokens with configurable reserves
- *   - Provides context limit checking and error messaging
- *   - Helps prevent context window overflow
- *
- * - **SlotsService**: Provides current context usage from server slots
- * - **ChatStore**: Uses context checking before sending messages
- * - **UI Components**: Display context usage warnings and limits
- *
- * **Key Features:**
- * - **Real-time Context Checking**: Uses live server data for accuracy
- * - **Token Reservation**: Reserves tokens for response generation
- * - **Limit Detection**: Prevents context window overflow
- * - **Usage Reporting**: Detailed context usage statistics
- * - **Error Messaging**: User-friendly context limit messages
- * - **Configurable Reserves**: Adjustable token reservation for responses
- *
- * **Context Management:**
- * - Monitors current context usage from active slots
- * - Calculates available space considering reserved tokens
- * - Provides early warning before context limits are reached
- * - Helps optimize conversation length and content
- */
-export class ContextService {
-	private reserveTokens: number;
-
-	constructor(reserveTokens = 512) {
-		this.reserveTokens = reserveTokens;
-	}
-
-	/**
-	 * Checks if the context limit would be exceeded
-	 *
-	 * @returns {Promise<ContextCheckResult | null>} Promise that resolves to the context check result or null if an error occurs
-	 */
-	async checkContextLimit(): Promise<ContextCheckResult | null> {
-		try {
-			const currentState = await slotsService.getCurrentState();
-
-			if (!currentState) {
-				return null;
-			}
-
-			const maxContext = currentState.contextTotal;
-			const currentUsage = currentState.contextUsed;
-			const availableTokens = maxContext - currentUsage - this.reserveTokens;
-			const wouldExceed = availableTokens <= 0;
-
-			return {
-				wouldExceed,
-				currentUsage,
-				maxContext,
-				availableTokens: Math.max(0, availableTokens),
-				reservedTokens: this.reserveTokens
-			};
-		} catch (error) {
-			console.warn('Error checking context limit:', error);
-			return null;
-		}
-	}
-
-	/**
-	 * Returns a formatted error message for context limit exceeded
-	 *
-	 * @param {ContextCheckResult} result - Context check result
-	 * @returns {string} Formatted error message
-	 */
-	getContextErrorMessage(result: ContextCheckResult): string {
-		const usagePercent = Math.round((result.currentUsage / result.maxContext) * 100);
-		return `Context window is nearly full. Current usage: ${result.currentUsage.toLocaleString()}/${result.maxContext.toLocaleString()} tokens (${usagePercent}%). Available space: ${result.availableTokens.toLocaleString()} tokens (${result.reservedTokens} reserved for response).`;
-	}
-
-	/**
-	 * Sets the number of tokens to reserve for response generation
-	 *
-	 * @param {number} tokens - Number of tokens to reserve
-	 */
-	setReserveTokens(tokens: number): void {
-		this.reserveTokens = tokens;
-	}
-}
-
-export const contextService = new ContextService();
diff --git a/tools/server/webui/src/lib/services/index.ts b/tools/server/webui/src/lib/services/index.ts
index e5a1173ff76d8..9a9774bd56cfe 100644
--- a/tools/server/webui/src/lib/services/index.ts
+++ b/tools/server/webui/src/lib/services/index.ts
@@ -1,3 +1,2 @@
 export { chatService } from './chat';
-export { contextService } from './context';
 export { slotsService } from './slots';
diff --git a/tools/server/webui/src/lib/stores/chat.svelte.ts b/tools/server/webui/src/lib/stores/chat.svelte.ts
index 9bac1b9d36f9b..5b77abb4cb21c 100644
--- a/tools/server/webui/src/lib/stores/chat.svelte.ts
+++ b/tools/server/webui/src/lib/stores/chat.svelte.ts
@@ -39,7 +39,6 @@ import type { ExportedConversations } from '$lib/types/database';
  * - Conversation branching for exploring different response paths
  * - Streaming AI responses with real-time content updates
  * - File attachment support (images, PDFs, text files, audio)
- * - Context window management with error recovery
  * - Partial response saving when generation is interrupted
  * - Message editing with automatic response regeneration
  */
@@ -48,11 +47,9 @@ class ChatStore {
 	activeMessages = $state<DatabaseMessage[]>([]);
 	conversations = $state<DatabaseConversation[]>([]);
 	currentResponse = $state('');
+	errorDialogState = $state<{ type: 'timeout' | 'server'; message: string } | null>(null);
 	isInitialized = $state(false);
 	isLoading = $state(false);
-	maxContextError = $state<{ message: string; estimatedTokens: number; maxContext: number } | null>(
-		null
-	);
 	titleUpdateConfirmationCallback?: (currentTitle: string, newTitle: string) => Promise<boolean>;
 
 	constructor() {
@@ -69,8 +66,6 @@ class ChatStore {
 		try {
 			await this.loadConversations();
 
-			this.maxContextError = null;
-
 			this.isInitialized = true;
 		} catch (error) {
 			console.error('Failed to initialize chat store:', error);
@@ -99,8 +94,6 @@ class ChatStore {
 		this.activeConversation = conversation;
 		this.activeMessages = [];
 
-		this.maxContextError = null;
-
 		await goto(`#/chat/${conversation.id}`);
 
 		return conversation.id;
@@ -133,8 +126,6 @@ class ChatStore {
 				this.activeMessages = await DatabaseStore.getConversationMessages(convId);
 			}
 
-			this.maxContextError = null;
-
 			return true;
 		} catch (error) {
 			console.error('Failed to load conversation:', error);
@@ -418,56 +409,6 @@ class ChatStore {
 					return;
 				}
 
-				if (error.name === 'ContextError') {
-					console.warn('Context error detected:', error.message);
-					this.isLoading = false;
-					this.currentResponse = '';
-
-					const messageIndex = this.activeMessages.findIndex(
-						(m: DatabaseMessage) => m.id === assistantMessage.id
-					);
-
-					if (messageIndex !== -1) {
-						this.activeMessages.splice(messageIndex, 1);
-						DatabaseStore.deleteMessage(assistantMessage.id).catch(console.error);
-					}
-
-					// Use structured context info from new exceed_context_size_error format if available
-					const contextInfo = (
-						error as Error & {
-							contextInfo?: { promptTokens: number; maxContext: number; estimatedTokens: number };
-						}
-					).contextInfo;
-					let estimatedTokens = 0;
-					let maxContext = serverStore.serverProps?.default_generation_settings.n_ctx || 8192;
-
-					if (contextInfo) {
-						// Use precise token counts from server response
-						estimatedTokens = contextInfo.promptTokens;
-						maxContext = contextInfo.maxContext;
-					} else {
-						// Fallback to estimation for older error format
-						try {
-							// Rough estimation: ~4 characters per token
-							const messageContent = JSON.stringify(messages);
-							estimatedTokens = Math.ceil(messageContent.length / 4);
-						} catch {
-							estimatedTokens = 0;
-						}
-					}
-
-					this.maxContextError = {
-						message: error.message,
-						estimatedTokens,
-						maxContext
-					};
-
-					if (onError) {
-						onError(error);
-					}
-					return;
-				}
-
 				console.error('Streaming error:', error);
 				this.isLoading = false;
 				this.currentResponse = '';
@@ -477,9 +418,19 @@ class ChatStore {
 				);
 
 				if (messageIndex !== -1) {
-					this.activeMessages[messageIndex].content = `Error: ${error.message}`;
+					const [failedMessage] = this.activeMessages.splice(messageIndex, 1);
+
+					if (failedMessage) {
+						DatabaseStore.deleteMessage(failedMessage.id).catch((cleanupError) => {
+							console.error('Failed to remove assistant message after error:', cleanupError);
+						});
+					}
 				}
 
+				const dialogType = error.name === 'TimeoutError' ? 'timeout' : 'server';
+
+				this.showErrorDialog(dialogType, error.message);
+
 				if (onError) {
 					onError(error);
 				}
@@ -487,6 +438,14 @@ class ChatStore {
 		});
 	}
 
+	private showErrorDialog(type: 'timeout' | 'server', message: string): void {
+		this.errorDialogState = { type, message };
+	}
+
+	dismissErrorDialog(): void {
+		this.errorDialogState = null;
+	}
+
 	/**
 	 * Checks if an error is an abort error (user cancelled operation)
 	 * @param error - The error to check
@@ -574,6 +533,7 @@ class ChatStore {
 			return;
 		}
 
+		this.errorDialogState = null;
 		this.isLoading = true;
 		this.currentResponse = '';
 
@@ -603,37 +563,23 @@ class ChatStore {
 
 			const conversationContext = this.activeMessages.slice(0, -1);
 
-			await this.streamChatCompletion(
-				conversationContext,
-				assistantMessage,
-				undefined,
-				(error: Error) => {
-					if (error.name === 'ContextError' && userMessage) {
-						const userMessageIndex = this.findMessageIndex(userMessage.id);
-
-						if (userMessageIndex !== -1) {
-							this.activeMessages.splice(userMessageIndex, 1);
-							DatabaseStore.deleteMessage(userMessage.id).catch(console.error);
-						}
-					}
-				}
-			);
+			await this.streamChatCompletion(conversationContext, assistantMessage);
 		} catch (error) {
 			if (this.isAbortError(error)) {
 				this.isLoading = false;
 				return;
 			}
 
-			if (error instanceof Error && error.name === 'ContextError' && userMessage) {
-				const userMessageIndex = this.findMessageIndex(userMessage.id);
-				if (userMessageIndex !== -1) {
-					this.activeMessages.splice(userMessageIndex, 1);
-					DatabaseStore.deleteMessage(userMessage.id).catch(console.error);
-				}
-			}
-
 			console.error('Failed to send message:', error);
 			this.isLoading = false;
+			if (!this.errorDialogState) {
+				if (error instanceof Error) {
+					const dialogType = error.name === 'TimeoutError' ? 'timeout' : 'server';
+					this.showErrorDialog(dialogType, error.message);
+				} else {
+					this.showErrorDialog('server', 'Unknown error occurred while sending message');
+				}
+			}
 		}
 	}
 
@@ -662,24 +608,6 @@ class ChatStore {
 		this.currentResponse = '';
 	}
 
-	/**
-	 * Clears the max context error state
-	 * Removes any displayed context limit warnings
-	 */
-	clearMaxContextError(): void {
-		this.maxContextError = null;
-	}
-
-	/**
-	 * Sets the max context error state
-	 * @param error - The context error details or null to clear
-	 */
-	setMaxContextError(
-		error: { message: string; estimatedTokens: number; maxContext: number } | null
-	): void {
-		this.maxContextError = error;
-	}
-
 	/**
 	 * Saves partial response if generation was interrupted
 	 * Preserves user's partial content and timing data when generation is stopped early
@@ -1250,7 +1178,6 @@ class ChatStore {
 		this.activeMessages = [];
 		this.currentResponse = '';
 		this.isLoading = false;
-		this.maxContextError = null;
 	}
 
 	/** Refreshes active messages based on currNode after branch navigation */
@@ -1538,6 +1465,7 @@ class ChatStore {
 	private async generateResponseForMessage(userMessageId: string): Promise<void> {
 		if (!this.activeConversation) return;
 
+		this.errorDialogState = null;
 		this.isLoading = true;
 		this.currentResponse = '';
 
@@ -1584,7 +1512,7 @@ export const activeMessages = () => chatStore.activeMessages;
 export const isLoading = () => chatStore.isLoading;
 export const currentResponse = () => chatStore.currentResponse;
 export const isInitialized = () => chatStore.isInitialized;
-export const maxContextError = () => chatStore.maxContextError;
+export const errorDialog = () => chatStore.errorDialogState;
 
 export const createConversation = chatStore.createConversation.bind(chatStore);
 export const downloadConversation = chatStore.downloadConversation.bind(chatStore);
@@ -1592,9 +1520,9 @@ export const exportAllConversations = chatStore.exportAllConversations.bind(chat
 export const importConversations = chatStore.importConversations.bind(chatStore);
 export const deleteConversation = chatStore.deleteConversation.bind(chatStore);
 export const sendMessage = chatStore.sendMessage.bind(chatStore);
+export const dismissErrorDialog = chatStore.dismissErrorDialog.bind(chatStore);
+
 export const gracefulStop = chatStore.gracefulStop.bind(chatStore);
-export const clearMaxContextError = chatStore.clearMaxContextError.bind(chatStore);
-export const setMaxContextError = chatStore.setMaxContextError.bind(chatStore);
 
 // Branching operations
 export const refreshActiveMessages = chatStore.refreshActiveMessages.bind(chatStore);
diff --git a/tools/server/webui/src/lib/stores/server.svelte.ts b/tools/server/webui/src/lib/stores/server.svelte.ts
index a8624562d1c5f..0b6855404c7db 100644
--- a/tools/server/webui/src/lib/stores/server.svelte.ts
+++ b/tools/server/webui/src/lib/stores/server.svelte.ts
@@ -197,7 +197,7 @@ class ServerStore {
 					errorMessage = 'Server not found - check server address';
 					isOfflineLikeError = true;
 				} else if (error.message.includes('ETIMEDOUT')) {
-					errorMessage = 'Connection timeout - server may be overloaded';
+					errorMessage = 'Request timed out - the server took too long to respond';
 					isOfflineLikeError = true;
 				} else if (error.message.includes('503')) {
 					errorMessage = 'Server temporarily unavailable - try again shortly';
diff --git a/tools/server/webui/src/routes/+layout.svelte b/tools/server/webui/src/routes/+layout.svelte
index bc204291960ce..0245cf3abcef4 100644
--- a/tools/server/webui/src/routes/+layout.svelte
+++ b/tools/server/webui/src/routes/+layout.svelte
@@ -1,11 +1,7 @@
 <script lang="ts">
 	import '../app.css';
 	import { page } from '$app/state';
-	import {
-		ChatSidebar,
-		ConversationTitleUpdateDialog,
-		MaximumContextAlertDialog
-	} from '$lib/components/app';
+	import { ChatSidebar, ConversationTitleUpdateDialog } from '$lib/components/app';
 	import {
 		activeMessages,
 		isLoading,
@@ -145,8 +141,6 @@
 
 <Toaster richColors />
 
-<MaximumContextAlertDialog />
-
 <ConversationTitleUpdateDialog
 	bind:open={titleUpdateDialogOpen}
 	currentTitle={titleUpdateCurrentTitle}