diff --git a/apps/server/src/routes/context/routes/describe-file.ts b/apps/server/src/routes/context/routes/describe-file.ts
index e6b58a83..3b30347c 100644
--- a/apps/server/src/routes/context/routes/describe-file.ts
+++ b/apps/server/src/routes/context/routes/describe-file.ts
@@ -13,10 +13,11 @@
 import type { Request, Response } from 'express';
 import { query } from '@anthropic-ai/claude-agent-sdk';
 import { createLogger } from '@automaker/utils';
-import { DEFAULT_PHASE_MODELS } from '@automaker/types';
+import { DEFAULT_PHASE_MODELS, isCursorModel } from '@automaker/types';
 import { PathNotAllowedError } from '@automaker/platform';
 import { resolveModelString } from '@automaker/model-resolver';
 import { createCustomOptions } from '../../../lib/sdk-options.js';
+import { ProviderFactory } from '../../../providers/provider-factory.js';
 import * as secureFs from '../../../lib/secure-fs.js';
 import * as path from 'path';
 import type { SettingsService } from '../../../services/settings-service.js';
@@ -187,30 +188,64 @@ File: ${fileName}${truncated ? ' (truncated)' : ''}`;
 
       logger.debug(`[DescribeFile] Using model: ${model}`);
 
-      // Use centralized SDK options with proper cwd validation
-      // No tools needed since we're passing file content directly
-      const sdkOptions = createCustomOptions({
-        cwd,
-        model,
-        maxTurns: 1,
-        allowedTools: [],
-        autoLoadClaudeMd,
-        sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
-      });
+      let description: string;
 
-      const promptGenerator = (async function* () {
-        yield {
-          type: 'user' as const,
-          session_id: '',
-          message: { role: 'user' as const, content: promptContent },
-          parent_tool_use_id: null,
-        };
-      })();
+      // Route to appropriate provider based on model type
+      if (isCursorModel(model)) {
+        // Use Cursor provider for Cursor models
+        logger.info(`[DescribeFile] Using Cursor provider for model: ${model}`);
 
-      const stream = query({ prompt: promptGenerator, options: sdkOptions });
+        const provider = ProviderFactory.getProviderForModel(model);
 
-      // Extract the description from the response
-      const description = await extractTextFromStream(stream);
+        // Build a simple text prompt for Cursor (no multi-part content blocks)
+        const cursorPrompt = `${instructionText}\n\n--- FILE CONTENT ---\n${contentToAnalyze}`;
+
+        let responseText = '';
+        for await (const msg of provider.executeQuery({
+          prompt: cursorPrompt,
+          model,
+          cwd,
+          maxTurns: 1,
+          allowedTools: [],
+        })) {
+          if (msg.type === 'assistant' && msg.message?.content) {
+            for (const block of msg.message.content) {
+              if (block.type === 'text' && block.text) {
+                responseText += block.text;
+              }
+            }
+          }
+        }
+        description = responseText;
+      } else {
+        // Use Claude SDK for Claude models
+        logger.info(`[DescribeFile] Using Claude SDK for model: ${model}`);
+
+        // Use centralized SDK options with proper cwd validation
+        // No tools needed since we're passing file content directly
+        const sdkOptions = createCustomOptions({
+          cwd,
+          model,
+          maxTurns: 1,
+          allowedTools: [],
+          autoLoadClaudeMd,
+          sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
+        });
+
+        const promptGenerator = (async function* () {
+          yield {
+            type: 'user' as const,
+            session_id: '',
+            message: { role: 'user' as const, content: promptContent },
+            parent_tool_use_id: null,
+          };
+        })();
+
+        const stream = query({ prompt: promptGenerator, options: sdkOptions });
+
+        // Extract the description from the response
+        description = await extractTextFromStream(stream);
+      }
 
       if (!description || description.trim().length === 0) {
         logger.warn('Received empty response from Claude');
diff --git a/apps/server/src/routes/context/routes/describe-image.ts b/apps/server/src/routes/context/routes/describe-image.ts
index 4424aeb9..3b87bd7b 100644
--- a/apps/server/src/routes/context/routes/describe-image.ts
+++ b/apps/server/src/routes/context/routes/describe-image.ts
@@ -14,9 +14,10 @@
 import type { Request, Response } from 'express';
 import { query } from '@anthropic-ai/claude-agent-sdk';
 import { createLogger, readImageAsBase64 } from '@automaker/utils';
-import { DEFAULT_PHASE_MODELS } from '@automaker/types';
+import { DEFAULT_PHASE_MODELS, isCursorModel } from '@automaker/types';
 import { resolveModelString } from '@automaker/model-resolver';
 import { createCustomOptions } from '../../../lib/sdk-options.js';
+import { ProviderFactory } from '../../../providers/provider-factory.js';
 import * as fs from 'fs';
 import * as path from 'path';
 import type { SettingsService } from '../../../services/settings-service.js';
@@ -347,40 +348,79 @@ export function createDescribeImageHandler(
 
       logger.info(`[${requestId}] Using model: ${model}`);
 
-      // Use the same centralized option builder used across the server (validates cwd)
-      const sdkOptions = createCustomOptions({
-        cwd,
-        model,
-        maxTurns: 1,
-        allowedTools: [],
-        autoLoadClaudeMd,
-        sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
-      });
+      let description: string;
 
-      logger.info(
-        `[${requestId}] SDK options model=${sdkOptions.model} maxTurns=${sdkOptions.maxTurns} allowedTools=${JSON.stringify(
-          sdkOptions.allowedTools
-        )} sandbox=${JSON.stringify(sdkOptions.sandbox)}`
-      );
+      // Route to appropriate provider based on model type
+      if (isCursorModel(model)) {
+        // Use Cursor provider for Cursor models
+        // Note: Cursor may have limited support for image content blocks
+        logger.info(`[${requestId}] Using Cursor provider for model: ${model}`);
 
-      const promptGenerator = (async function* () {
-        yield {
-          type: 'user' as const,
-          session_id: '',
-          message: { role: 'user' as const, content: promptContent },
-          parent_tool_use_id: null,
-        };
-      })();
+        const provider = ProviderFactory.getProviderForModel(model);
 
-      logger.info(`[${requestId}] Calling query()...`);
-      const queryStart = Date.now();
-      const stream = query({ prompt: promptGenerator, options: sdkOptions });
-      logger.info(`[${requestId}] query() returned stream in ${Date.now() - queryStart}ms`);
+        // Build prompt with image reference for Cursor
+        // Note: Cursor CLI may not support base64 image blocks directly,
+        // so we include the image path as context
+        const cursorPrompt = `${instructionText}\n\nImage file: ${actualPath}\nMIME type: ${imageData.mimeType}`;
 
-      // Extract the description from the response
-      const extractStart = Date.now();
-      const description = await extractTextFromStream(stream, requestId);
-      logger.info(`[${requestId}] extractMs=${Date.now() - extractStart}`);
+        let responseText = '';
+        const queryStart = Date.now();
+        for await (const msg of provider.executeQuery({
+          prompt: cursorPrompt,
+          model,
+          cwd,
+          maxTurns: 1,
+          allowedTools: ['Read'], // Allow Read tool so Cursor can read the image if needed
+        })) {
+          if (msg.type === 'assistant' && msg.message?.content) {
+            for (const block of msg.message.content) {
+              if (block.type === 'text' && block.text) {
+                responseText += block.text;
+              }
+            }
+          }
+        }
+        logger.info(`[${requestId}] Cursor query completed in ${Date.now() - queryStart}ms`);
+        description = responseText;
+      } else {
+        // Use Claude SDK for Claude models (supports image content blocks)
+        logger.info(`[${requestId}] Using Claude SDK for model: ${model}`);
+
+        // Use the same centralized option builder used across the server (validates cwd)
+        const sdkOptions = createCustomOptions({
+          cwd,
+          model,
+          maxTurns: 1,
+          allowedTools: [],
+          autoLoadClaudeMd,
+          sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
+        });
+
+        logger.info(
+          `[${requestId}] SDK options model=${sdkOptions.model} maxTurns=${sdkOptions.maxTurns} allowedTools=${JSON.stringify(
+            sdkOptions.allowedTools
+          )} sandbox=${JSON.stringify(sdkOptions.sandbox)}`
+        );
+
+        const promptGenerator = (async function* () {
+          yield {
+            type: 'user' as const,
+            session_id: '',
+            message: { role: 'user' as const, content: promptContent },
+            parent_tool_use_id: null,
+          };
+        })();
+
+        logger.info(`[${requestId}] Calling query()...`);
+        const queryStart = Date.now();
+        const stream = query({ prompt: promptGenerator, options: sdkOptions });
+        logger.info(`[${requestId}] query() returned stream in ${Date.now() - queryStart}ms`);
+
+        // Extract the description from the response
+        const extractStart = Date.now();
+        description = await extractTextFromStream(stream, requestId);
+        logger.info(`[${requestId}] extractMs=${Date.now() - extractStart}`);
+      }
 
       if (!description || description.trim().length === 0) {
         logger.warn(`[${requestId}] Received empty response from Claude`);
diff --git a/apps/server/src/services/auto-mode-service.ts b/apps/server/src/services/auto-mode-service.ts
index f6281382..98231c36 100644
--- a/apps/server/src/services/auto-mode-service.ts
+++ b/apps/server/src/services/auto-mode-service.ts
@@ -1146,7 +1146,7 @@ Format your response as a structured markdown document.`;
       const projectAnalysisModel =
         settings?.phaseModels?.projectAnalysisModel || DEFAULT_PHASE_MODELS.projectAnalysisModel;
       const analysisModel = resolveModelString(projectAnalysisModel, DEFAULT_MODELS.claude);
-      this.logger.info('[AutoMode] Using model for project analysis:', analysisModel);
+      console.log('[AutoMode] Using model for project analysis:', analysisModel);
 
       const provider = ProviderFactory.getProviderForModel(analysisModel);