diff --git a/src/agents/clawdbot-tools.ts b/src/agents/clawdbot-tools.ts
index 5ae4891dc..98717cd3b 100644
--- a/src/agents/clawdbot-tools.ts
+++ b/src/agents/clawdbot-tools.ts
@@ -41,12 +41,15 @@ export function createClawdbotTools(options?: {
   replyToMode?: "off" | "first" | "all";
   /** Mutable ref to track if a reply was sent (for "first" mode). */
   hasRepliedRef?: { value: boolean };
+  /** If true, the model has native vision capability */
+  modelHasVision?: boolean;
 }): AnyAgentTool[] {
   const imageTool = options?.agentDir?.trim()
     ? createImageTool({
         config: options?.config,
         agentDir: options.agentDir,
         sandboxRoot: options?.sandboxRoot,
+        modelHasVision: options?.modelHasVision,
       })
     : null;
   const webSearchTool = createWebSearchTool({
diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index 407a25246..94a80dcb5 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -2,7 +2,7 @@ import fs from "node:fs/promises";
 import os from "node:os";
 
 import type { AgentMessage } from "@mariozechner/pi-agent-core";
-import type { AssistantMessage } from "@mariozechner/pi-ai";
+import type { AssistantMessage, ImageContent } from "@mariozechner/pi-ai";
 import { streamSimple } from "@mariozechner/pi-ai";
 import { createAgentSession, SessionManager, SettingsManager } from "@mariozechner/pi-coding-agent";
 
@@ -69,7 +69,9 @@ import { resolveSandboxRuntimeStatus } from "../../sandbox/runtime-status.js";
 import { isTimeoutError } from "../../failover-error.js";
 import { getGlobalHookRunner } from "../../../plugins/hook-runner-global.js";
 
+import { MAX_IMAGE_BYTES } from "../../../media/constants.js";
 import type { EmbeddedRunAttemptParams, EmbeddedRunAttemptResult } from "./types.js";
+import { detectAndLoadPromptImages } from "./images.js";
 
 export async function runEmbeddedAttempt(
   params: EmbeddedRunAttemptParams,
@@ -133,6 +135,9 @@ export async function runEmbeddedAttempt(
 
     const agentDir = params.agentDir ?? resolveClawdbotAgentDir();
 
+    // Check if the model supports native image input
+    const modelHasVision = params.model.input?.includes("image") ?? false;
+
     const toolsRaw = createClawdbotCodingTools({
       exec: {
         ...params.execOverrides,
@@ -153,6 +158,7 @@ export async function runEmbeddedAttempt(
       currentThreadTs: params.currentThreadTs,
       replyToMode: params.replyToMode,
       hasRepliedRef: params.hasRepliedRef,
+      modelHasVision,
     });
     const tools = sanitizeToolsForGoogle({ tools: toolsRaw, provider: params.provider });
     logToolSchemasForGoogle({ tools, provider: params.provider });
@@ -530,7 +536,60 @@ export async function runEmbeddedAttempt(
         }
 
         try {
-          await abortable(activeSession.prompt(effectivePrompt, { images: params.images }));
+          // Detect and load images referenced in the prompt for vision-capable models.
+          // This eliminates the need for an explicit "view" tool call by injecting
+          // images directly into the prompt when the model supports it.
+          // Also scans conversation history to enable follow-up questions about earlier images.
+          const imageResult = await detectAndLoadPromptImages({
+            prompt: effectivePrompt,
+            workspaceDir: effectiveWorkspace,
+            model: params.model,
+            existingImages: params.images,
+            historyMessages: activeSession.messages,
+            maxBytes: MAX_IMAGE_BYTES,
+            // Enforce sandbox path restrictions when sandbox is enabled
+            sandboxRoot: sandbox?.enabled ? sandbox.workspaceDir : undefined,
+          });
+
+          // Inject history images into their original message positions.
+          // This ensures the model sees images in context (e.g., "compare to the first image").
+          if (imageResult.historyImagesByIndex.size > 0) {
+            for (const [msgIndex, images] of imageResult.historyImagesByIndex) {
+              // Bounds check: ensure index is valid before accessing
+              if (msgIndex < 0 || msgIndex >= activeSession.messages.length) continue;
+              const msg = activeSession.messages[msgIndex];
+              if (msg && msg.role === "user") {
+                // Convert string content to array format if needed
+                if (typeof msg.content === "string") {
+                  msg.content = [{ type: "text", text: msg.content }];
+                }
+                if (Array.isArray(msg.content)) {
+                  // Check for existing image content to avoid duplicates across turns
+                  const existingImageData = new Set(
+                    msg.content
+                      .filter((c): c is ImageContent =>
+                        c != null && typeof c === "object" && c.type === "image" && typeof c.data === "string",
+                      )
+                      .map((c) => c.data),
+                  );
+                  for (const img of images) {
+                    // Only add if this image isn't already in the message
+                    if (!existingImageData.has(img.data)) {
+                      msg.content.push(img);
+                    }
+                  }
+                }
+              }
+            }
+          }
+
+          // Only pass images option if there are actually images to pass
+          // This avoids potential issues with models that don't expect the images parameter
+          if (imageResult.images.length > 0) {
+            await abortable(activeSession.prompt(effectivePrompt, { images: imageResult.images }));
+          } else {
+            await abortable(activeSession.prompt(effectivePrompt));
+          }
         } catch (err) {
           promptError = err;
         } finally {
diff --git a/src/agents/pi-embedded-runner/run/images.test.ts b/src/agents/pi-embedded-runner/run/images.test.ts
new file mode 100644
index 000000000..918f2027c
--- /dev/null
+++ b/src/agents/pi-embedded-runner/run/images.test.ts
@@ -0,0 +1,218 @@
+import { describe, expect, it } from "vitest";
+
+import { detectImageReferences, modelSupportsImages } from "./images.js";
+
+describe("detectImageReferences", () => {
+  it("detects absolute file paths with common extensions", () => {
+    const prompt = "Check this image /path/to/screenshot.png and tell me what you see";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]).toEqual({
+      raw: "/path/to/screenshot.png",
+      type: "path",
+      resolved: "/path/to/screenshot.png",
+    });
+  });
+
+  it("detects relative paths starting with ./", () => {
+    const prompt = "Look at ./images/photo.jpg";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("./images/photo.jpg");
+    expect(refs[0]?.type).toBe("path");
+  });
+
+  it("detects relative paths starting with ../", () => {
+    const prompt = "The file is at ../screenshots/test.jpeg";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("../screenshots/test.jpeg");
+    expect(refs[0]?.type).toBe("path");
+  });
+
+  it("detects home directory paths starting with ~/", () => {
+    const prompt = "My photo is at ~/Pictures/vacation.png";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("~/Pictures/vacation.png");
+    expect(refs[0]?.type).toBe("path");
+    // Resolved path should expand ~
+    expect(refs[0]?.resolved).not.toContain("~");
+  });
+
+  it("detects HTTP URLs with image extensions", () => {
+    const prompt = "Check this URL: https://mysite.com/images/logo.png";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]).toEqual({
+      raw: "https://mysite.com/images/logo.png",
+      type: "url",
+      resolved: "https://mysite.com/images/logo.png",
+    });
+  });
+
+  it("detects HTTPS URLs with query parameters", () => {
+    const prompt = "Image from https://cdn.mysite.com/img.jpg?size=large&v=2";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.type).toBe("url");
+    expect(refs[0]?.raw).toContain("https://cdn.mysite.com/img.jpg");
+  });
+
+  it("detects multiple image references in a prompt", () => {
+    const prompt = `
+      Compare these two images:
+      1. /home/user/photo1.png
+      2. https://mysite.com/photo2.jpg
+    `;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(2);
+    expect(refs.some((r) => r.type === "path")).toBe(true);
+    expect(refs.some((r) => r.type === "url")).toBe(true);
+  });
+
+  it("handles various image extensions", () => {
+    const extensions = ["png", "jpg", "jpeg", "gif", "webp", "bmp", "tiff", "heic"];
+    for (const ext of extensions) {
+      const prompt = `Image: /test/image.${ext}`;
+      const refs = detectImageReferences(prompt);
+      expect(refs.length).toBeGreaterThanOrEqual(1);
+      expect(refs[0]?.raw).toContain(`.${ext}`);
+    }
+  });
+
+  it("deduplicates repeated image references", () => {
+    const prompt = "Look at /path/image.png and also /path/image.png again";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+  });
+
+  it("returns empty array when no images found", () => {
+    const prompt = "Just some text without any image references";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(0);
+  });
+
+  it("ignores non-image file extensions", () => {
+    const prompt = "Check /path/to/document.pdf and /code/file.ts";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(0);
+  });
+
+  it("handles paths inside quotes (without spaces)", () => {
+    const prompt = 'The file is at "/path/to/image.png"';
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("/path/to/image.png");
+  });
+
+  it("handles paths in parentheses", () => {
+    const prompt = "See the image (./screenshot.png) for details";
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("./screenshot.png");
+  });
+
+  it("detects [Image: source: ...] format from messaging systems", () => {
+    const prompt = `What does this image show?
+[Image: source: /Users/tyleryust/Library/Messages/Attachments/IMG_0043.jpeg]`;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("/Users/tyleryust/Library/Messages/Attachments/IMG_0043.jpeg");
+    expect(refs[0]?.type).toBe("path");
+  });
+
+  it("handles complex message attachment paths", () => {
+    const prompt = `[Image: source: /Users/tyleryust/Library/Messages/Attachments/23/03/AA4726EA-DB27-4269-BA56-1436936CC134/5E3E286A-F585-4E5E-9043-5BC2AFAFD81BIMG_0043.jpeg]`;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.resolved).toContain("IMG_0043.jpeg");
+  });
+
+  it("detects multiple images in [media attached: ...] format", () => {
+    // Multi-file format uses separate brackets on separate lines
+    const prompt = `[media attached: 2 files]
+[media attached 1/2: /Users/tyleryust/.clawdbot/media/IMG_6430.jpeg (image/jpeg)]
+[media attached 2/2: /Users/tyleryust/.clawdbot/media/IMG_6431.jpeg (image/jpeg)]
+what about these images?`;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(2);
+    expect(refs[0]?.resolved).toContain("IMG_6430.jpeg");
+    expect(refs[1]?.resolved).toContain("IMG_6431.jpeg");
+  });
+
+  it("does not double-count path and url in same bracket", () => {
+    // Single file with URL (| separates path from url, not multiple files)
+    const prompt = `[media attached: /cache/IMG_6430.jpeg (image/jpeg) | /cache/IMG_6430.jpeg]`;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.resolved).toContain("IMG_6430.jpeg");
+  });
+
+  it("skips example.com URLs as they are documentation examples", () => {
+    const prompt = `To send an image: MEDIA:https://example.com/image.jpg
+Here is my actual image: /path/to/real.png`;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.raw).toBe("/path/to/real.png");
+  });
+
+  it("handles single file format with URL (no index)", () => {
+    const prompt = `[media attached: /cache/photo.jpeg (image/jpeg) | https://example.com/url]
+what is this?`;
+    const refs = detectImageReferences(prompt);
+
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.resolved).toContain("photo.jpeg");
+  });
+
+  it("handles paths with spaces in filename", () => {
+    // URL after | is https, not a local path, so only the local path should be detected
+    const prompt = `[media attached: /Users/test/.clawdbot/media/ChatGPT Image Apr 21, 2025.png (image/png) | https://example.com/same.png]
+what is this?`;
+    const refs = detectImageReferences(prompt);
+
+    // Only 1 ref - the local path (example.com URLs are skipped)
+    expect(refs).toHaveLength(1);
+    expect(refs[0]?.resolved).toContain("ChatGPT Image Apr 21, 2025.png");
+  });
+});
+
+describe("modelSupportsImages", () => {
+  it("returns true when model input includes image", () => {
+    const model = { input: ["text", "image"] };
+    expect(modelSupportsImages(model)).toBe(true);
+  });
+
+  it("returns false when model input does not include image", () => {
+    const model = { input: ["text"] };
+    expect(modelSupportsImages(model)).toBe(false);
+  });
+
+  it("returns false when model input is undefined", () => {
+    const model = {};
+    expect(modelSupportsImages(model)).toBe(false);
+  });
+
+  it("returns false when model input is empty", () => {
+    const model = { input: [] };
+    expect(modelSupportsImages(model)).toBe(false);
+  });
+});
diff --git a/src/agents/pi-embedded-runner/run/images.ts b/src/agents/pi-embedded-runner/run/images.ts
new file mode 100644
index 000000000..f7de8b734
--- /dev/null
+++ b/src/agents/pi-embedded-runner/run/images.ts
@@ -0,0 +1,379 @@
+import fs from "node:fs/promises";
+import path from "node:path";
+
+import type { ImageContent } from "@mariozechner/pi-ai";
+
+import { assertSandboxPath } from "../../sandbox-paths.js";
+import { extractTextFromMessage } from "../../../tui/tui-formatters.js";
+import { loadWebMedia } from "../../../web/media.js";
+import { resolveUserPath } from "../../../utils.js";
+import { log } from "../logger.js";
+
+/**
+ * Common image file extensions for detection.
+ */
+const IMAGE_EXTENSIONS = new Set([
+  ".png",
+  ".jpg",
+  ".jpeg",
+  ".gif",
+  ".webp",
+  ".bmp",
+  ".tiff",
+  ".tif",
+  ".heic",
+  ".heif",
+]);
+
+/**
+ * Result of detecting an image reference in text.
+ */
+export interface DetectedImageRef {
+  /** The raw matched string from the prompt */
+  raw: string;
+  /** The type of reference (path or url) */
+  type: "path" | "url";
+  /** The resolved/normalized path or URL */
+  resolved: string;
+  /** Index of the message this ref was found in (for history images) */
+  messageIndex?: number;
+}
+
+/**
+ * Checks if a file extension indicates an image file.
+ */
+function isImageExtension(filePath: string): boolean {
+  const ext = path.extname(filePath).toLowerCase();
+  return IMAGE_EXTENSIONS.has(ext);
+}
+
+/**
+ * Detects image references in a user prompt.
+ *
+ * Patterns detected:
+ * - Absolute paths: /path/to/image.png
+ * - Relative paths: ./image.png, ../images/photo.jpg
+ * - Home paths: ~/Pictures/screenshot.png
+ * - HTTP(S) URLs: https://example.com/image.png
+ * - Message attachments: [Image: source: /path/to/image.jpg]
+ *
+ * @param prompt The user prompt text to scan
+ * @returns Array of detected image references
+ */
+export function detectImageReferences(prompt: string): DetectedImageRef[] {
+  const refs: DetectedImageRef[] = [];
+  const seen = new Set<string>();
+
+  // Helper to add a path ref
+  const addPathRef = (raw: string) => {
+    const trimmed = raw.trim();
+    if (!trimmed || seen.has(trimmed.toLowerCase())) return;
+    if (!isImageExtension(trimmed)) return;
+    seen.add(trimmed.toLowerCase());
+    const resolved = trimmed.startsWith("~") ? resolveUserPath(trimmed) : trimmed;
+    refs.push({ raw: trimmed, type: "path", resolved });
+  };
+
+  // Pattern for [media attached: path (type) | url] or [media attached N/M: path (type) | url] format
+  // Each bracket = ONE file. The | separates path from URL, not multiple files.
+  // Multi-file format uses separate brackets on separate lines.
+  const mediaAttachedPattern = /\[media attached(?:\s+\d+\/\d+)?:\s*([^\]]+)\]/gi;
+  let match: RegExpExecArray | null;
+  while ((match = mediaAttachedPattern.exec(prompt)) !== null) {
+    const content = match[1];
+
+    // Skip "[media attached: N files]" header lines
+    if (/^\d+\s+files?$/i.test(content.trim())) {
+      continue;
+    }
+
+    // Extract path before the (mime/type) or | delimiter
+    // Format is: path (type) | url  OR  just: path (type)
+    // Path may contain spaces (e.g., "ChatGPT Image Apr 21.png")
+    // Use non-greedy .+? to stop at first image extension
+    const pathMatch = content.match(
+      /^\s*(.+?\.(?:png|jpe?g|gif|webp|bmp|tiff?|heic|heif))\s*(?:\(|$|\|)/i,
+    );
+    if (pathMatch?.[1]) {
+      addPathRef(pathMatch[1].trim());
+    }
+  }
+
+  // Pattern for [Image: source: /path/...] format from messaging systems
+  const messageImagePattern = /\[Image:\s*source:\s*([^\]]+\.(?:png|jpe?g|gif|webp|bmp|tiff?|heic|heif))\]/gi;
+  while ((match = messageImagePattern.exec(prompt)) !== null) {
+    const raw = match[1]?.trim();
+    if (raw) addPathRef(raw);
+  }
+
+  // Pattern for HTTP(S) URLs ending in image extensions
+  // Skip example.com URLs as they're often just documentation examples
+  const urlPattern =
+    /https?:\/\/[^\s<>"'`\]]+\.(?:png|jpe?g|gif|webp|bmp|tiff?|heic|heif)(?:\?[^\s<>"'`\]]*)?/gi;
+  while ((match = urlPattern.exec(prompt)) !== null) {
+    const raw = match[0];
+    // Skip example.com URLs - they're documentation, not real images
+    if (raw.includes("example.com")) continue;
+    if (seen.has(raw.toLowerCase())) continue;
+    seen.add(raw.toLowerCase());
+    refs.push({ raw, type: "url", resolved: raw });
+  }
+
+  // Pattern for file paths (absolute, relative, or home)
+  // Matches:
+  // - /absolute/path/to/file.ext (including paths with special chars like Messages/Attachments)
+  // - ./relative/path.ext
+  // - ../parent/path.ext
+  // - ~/home/path.ext
+  const pathPattern = /(?:^|\s|["'`(])((\.\.?\/|[~/])[^\s"'`()[\]]*\.(?:png|jpe?g|gif|webp|bmp|tiff?|heic|heif))/gi;
+  while ((match = pathPattern.exec(prompt)) !== null) {
+    const raw = match[1] || match[0];
+    addPathRef(raw);
+  }
+
+  return refs;
+}
+
+/**
+ * Loads an image from a file path or URL and returns it as ImageContent.
+ *
+ * @param ref The detected image reference
+ * @param workspaceDir The current workspace directory for resolving relative paths
+ * @param options Optional settings for sandbox and size limits
+ * @returns The loaded image content, or null if loading failed
+ */
+export async function loadImageFromRef(
+  ref: DetectedImageRef,
+  workspaceDir: string,
+  options?: {
+    maxBytes?: number;
+    /** If set, enforce that file paths are within this sandbox root */
+    sandboxRoot?: string;
+  },
+): Promise<ImageContent | null> {
+  try {
+    let targetPath = ref.resolved;
+
+    // When sandbox is enabled, block remote URL loading to maintain network boundary
+    if (ref.type === "url" && options?.sandboxRoot) {
+      log.debug(`Native image: rejecting remote URL in sandboxed session: ${ref.resolved}`);
+      return null;
+    }
+
+    // For file paths, resolve relative to the appropriate root:
+    // - When sandbox is enabled, resolve relative to sandboxRoot for security
+    // - Otherwise, resolve relative to workspaceDir
+    if (ref.type === "path" && !path.isAbsolute(targetPath)) {
+      const resolveRoot = options?.sandboxRoot ?? workspaceDir;
+      targetPath = path.resolve(resolveRoot, targetPath);
+    }
+
+    // Enforce sandbox restrictions if sandboxRoot is set
+    if (ref.type === "path" && options?.sandboxRoot) {
+      try {
+        const validated = await assertSandboxPath({
+          filePath: targetPath,
+          cwd: options.sandboxRoot,
+          root: options.sandboxRoot,
+        });
+        targetPath = validated.resolved;
+      } catch (err) {
+        // Log the actual error for debugging (sandbox violation or other path error)
+        log.debug(`Native image: sandbox validation failed for ${ref.resolved}: ${err instanceof Error ? err.message : String(err)}`);
+        return null;
+      }
+    }
+
+    // Check file exists for local paths
+    if (ref.type === "path") {
+      try {
+        await fs.stat(targetPath);
+      } catch {
+        log.debug(`Native image: file not found: ${targetPath}`);
+        return null;
+      }
+    }
+
+    // loadWebMedia handles both file paths and HTTP(S) URLs
+    const media = await loadWebMedia(targetPath, options?.maxBytes);
+
+    if (media.kind !== "image") {
+      log.debug(`Native image: not an image file: ${targetPath} (got ${media.kind})`);
+      return null;
+    }
+
+    // EXIF orientation is already normalized by loadWebMedia -> resizeToJpeg
+    const mimeType = media.contentType ?? "image/png";
+    const data = media.buffer.toString("base64");
+
+    return { type: "image", data, mimeType };
+  } catch (err) {
+    // Log the actual error for debugging (size limits, network failures, etc.)
+    log.debug(`Native image: failed to load ${ref.resolved}: ${err instanceof Error ? err.message : String(err)}`);
+    return null;
+  }
+}
+
+/**
+ * Checks if a model supports image input based on its input capabilities.
+ *
+ * @param model The model object with input capability array
+ * @returns True if the model supports image input
+ */
+export function modelSupportsImages(model: { input?: string[] }): boolean {
+  return model.input?.includes("image") ?? false;
+}
+
+/**
+ * Extracts image references from conversation history messages.
+ * Scans user messages for image paths/URLs that can be loaded.
+ * Each ref includes the messageIndex so images can be injected at their original location.
+ *
+ * Note: Global deduplication is intentional - if the same image appears in multiple
+ * messages, we only inject it at the FIRST occurrence. This is sufficient because:
+ * 1. The model sees all message content including the image
+ * 2. Later references to "the image" or "that picture" will work since it's in context
+ * 3. Injecting duplicates would waste tokens and potentially hit size limits
+ */
+function detectImagesFromHistory(messages: unknown[]): DetectedImageRef[] {
+  const allRefs: DetectedImageRef[] = [];
+  const seen = new Set<string>();
+
+  for (let i = 0; i < messages.length; i++) {
+    const msg = messages[i];
+    if (!msg || typeof msg !== "object") continue;
+    const message = msg as { role?: string };
+    // Only scan user messages for image references
+    if (message.role !== "user") continue;
+
+    const text = extractTextFromMessage(msg);
+    if (!text) continue;
+
+    const refs = detectImageReferences(text);
+    for (const ref of refs) {
+      const key = ref.resolved.toLowerCase();
+      if (seen.has(key)) continue;
+      seen.add(key);
+      allRefs.push({ ...ref, messageIndex: i });
+    }
+  }
+
+  return allRefs;
+}
+
+/**
+ * Detects and loads images referenced in a prompt for models with vision capability.
+ *
+ * This function scans the prompt for image references (file paths and URLs),
+ * loads them, and returns them as ImageContent array ready to be passed to
+ * the model's prompt method.
+ *
+ * Also scans conversation history for images from previous turns and returns
+ * them mapped by message index so they can be injected at their original location.
+ *
+ * @param params Configuration for image detection and loading
+ * @returns Object with loaded images for current prompt and history images by message index
+ */
+export async function detectAndLoadPromptImages(params: {
+  prompt: string;
+  workspaceDir: string;
+  model: { input?: string[] };
+  existingImages?: ImageContent[];
+  historyMessages?: unknown[];
+  maxBytes?: number;
+  /** If set, enforce that file paths are within this sandbox root */
+  sandboxRoot?: string;
+}): Promise<{
+  /** Images for the current prompt (existingImages + detected in current prompt) */
+  images: ImageContent[];
+  /** Images from history messages, keyed by message index */
+  historyImagesByIndex: Map<number, ImageContent[]>;
+  detectedRefs: DetectedImageRef[];
+  loadedCount: number;
+  skippedCount: number;
+}> {
+  // If model doesn't support images, return empty results
+  if (!modelSupportsImages(params.model)) {
+    return {
+      images: params.existingImages ?? [],
+      historyImagesByIndex: new Map(),
+      detectedRefs: [],
+      loadedCount: 0,
+      skippedCount: 0,
+    };
+  }
+
+  // Detect images from current prompt
+  const promptRefs = detectImageReferences(params.prompt);
+
+  // Detect images from conversation history (with message indices)
+  const historyRefs = params.historyMessages
+    ? detectImagesFromHistory(params.historyMessages)
+    : [];
+
+  // Deduplicate: if an image is in the current prompt, don't also load it from history.
+  // Current prompt images are passed via the `images` parameter to prompt(), while history
+  // images are injected into their original message positions. We don't want the same
+  // image loaded and sent twice (wasting tokens and potentially causing confusion).
+  const seenPaths = new Set(promptRefs.map((r) => r.resolved.toLowerCase()));
+  const uniqueHistoryRefs = historyRefs.filter(
+    (r) => !seenPaths.has(r.resolved.toLowerCase()),
+  );
+
+  const allRefs = [...promptRefs, ...uniqueHistoryRefs];
+
+  if (allRefs.length === 0) {
+    return {
+      images: params.existingImages ?? [],
+      historyImagesByIndex: new Map(),
+      detectedRefs: [],
+      loadedCount: 0,
+      skippedCount: 0,
+    };
+  }
+
+  log.debug(
+    `Native image: detected ${allRefs.length} image refs (${promptRefs.length} in prompt, ${uniqueHistoryRefs.length} in history)`,
+  );
+
+  // Load images for current prompt
+  const promptImages: ImageContent[] = [...(params.existingImages ?? [])];
+  // Load images for history, grouped by message index
+  const historyImagesByIndex = new Map<number, ImageContent[]>();
+
+  let loadedCount = 0;
+  let skippedCount = 0;
+
+  for (const ref of allRefs) {
+    const image = await loadImageFromRef(ref, params.workspaceDir, {
+      maxBytes: params.maxBytes,
+      sandboxRoot: params.sandboxRoot,
+    });
+    if (image) {
+      if (ref.messageIndex !== undefined) {
+        // History image - add to the appropriate message index
+        const existing = historyImagesByIndex.get(ref.messageIndex);
+        if (existing) {
+          existing.push(image);
+        } else {
+          historyImagesByIndex.set(ref.messageIndex, [image]);
+        }
+      } else {
+        // Current prompt image
+        promptImages.push(image);
+      }
+      loadedCount++;
+      log.debug(`Native image: loaded ${ref.type} ${ref.resolved}`);
+    } else {
+      skippedCount++;
+    }
+  }
+
+  return {
+    images: promptImages,
+    historyImagesByIndex,
+    detectedRefs: allRefs,
+    loadedCount,
+    skippedCount,
+  };
+}
diff --git a/src/agents/pi-tools.ts b/src/agents/pi-tools.ts
index 33c4c27ad..d7d0a0c11 100644
--- a/src/agents/pi-tools.ts
+++ b/src/agents/pi-tools.ts
@@ -127,6 +127,8 @@ export function createClawdbotCodingTools(options?: {
   replyToMode?: "off" | "first" | "all";
   /** Mutable ref to track if a reply was sent (for "first" mode). */
   hasRepliedRef?: { value: boolean };
+  /** If true, the model has native vision capability */
+  modelHasVision?: boolean;
 }): AnyAgentTool[] {
   const execToolName = "exec";
   const sandbox = options?.sandbox?.enabled ? options.sandbox : undefined;
@@ -280,6 +282,7 @@ export function createClawdbotCodingTools(options?: {
       currentThreadTs: options?.currentThreadTs,
       replyToMode: options?.replyToMode,
       hasRepliedRef: options?.hasRepliedRef,
+      modelHasVision: options?.modelHasVision,
     }),
   ];
   const pluginGroups = buildPluginToolGroups({
diff --git a/src/agents/tools/image-tool.test.ts b/src/agents/tools/image-tool.test.ts
index 255e20183..9dcd94004 100644
--- a/src/agents/tools/image-tool.test.ts
+++ b/src/agents/tools/image-tool.test.ts
@@ -102,7 +102,11 @@ describe("image tool implicit imageModel config", () => {
     });
   });
 
-  it("disables image tool when primary model already supports images", async () => {
+  it("keeps image tool available when primary model supports images (for explicit requests)", async () => {
+    // When the primary model supports images, we still keep the tool available
+    // because images are auto-injected into prompts. The tool description is
+    // adjusted via modelHasVision to discourage redundant usage.
+    vi.stubEnv("OPENAI_API_KEY", "test-key");
     const agentDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-image-"));
     const cfg: ClawdbotConfig = {
       agents: {
@@ -119,8 +123,13 @@ describe("image tool implicit imageModel config", () => {
         },
       },
     };
-    expect(resolveImageModelConfigForTool({ cfg, agentDir })).toBeNull();
-    expect(createImageTool({ config: cfg, agentDir })).toBeNull();
+    // Tool should still be available for explicit image analysis requests
+    expect(resolveImageModelConfigForTool({ cfg, agentDir })).toEqual({
+      primary: "openai/gpt-5-mini",
+    });
+    const tool = createImageTool({ config: cfg, agentDir, modelHasVision: true });
+    expect(tool).not.toBeNull();
+    expect(tool?.description).toContain("Only use this tool when the image was NOT already provided");
   });
 
   it("sandboxes image paths like the read tool", async () => {
diff --git a/src/agents/tools/image-tool.ts b/src/agents/tools/image-tool.ts
index 52627e547..119423353 100644
--- a/src/agents/tools/image-tool.ts
+++ b/src/agents/tools/image-tool.ts
@@ -145,11 +145,10 @@ export function resolveImageModelConfigForTool(params: {
   cfg?: ClawdbotConfig;
   agentDir: string;
 }): ImageModelConfig | null {
-  const primarySupportsImages = resolvePrimaryModelSupportsImages({
-    cfg: params.cfg,
-    agentDir: params.agentDir,
-  });
-  if (primarySupportsImages === true) return null;
+  // Note: We intentionally do NOT gate based on primarySupportsImages here.
+  // Even when the primary model supports images, we keep the tool available
+  // because images are auto-injected into prompts (see attempt.ts detectAndLoadPromptImages).
+  // The tool description is adjusted via modelHasVision to discourage redundant usage.
   const explicit = coerceImageModelConfig(params.cfg);
   if (explicit.primary?.trim() || (explicit.fallbacks?.length ?? 0) > 0) {
     return explicit;
@@ -368,6 +367,8 @@ export function createImageTool(options?: {
   config?: ClawdbotConfig;
   agentDir?: string;
   sandboxRoot?: string;
+  /** If true, the model has native vision capability and images in the prompt are auto-injected */
+  modelHasVision?: boolean;
 }): AnyAgentTool | null {
   const agentDir = options?.agentDir?.trim();
   if (!agentDir) {
@@ -382,11 +383,17 @@ export function createImageTool(options?: {
     agentDir,
   });
   if (!imageModelConfig) return null;
+
+  // If model has native vision, images in the prompt are auto-injected
+  // so this tool is only needed when image wasn't provided in the prompt
+  const description = options?.modelHasVision
+    ? "Analyze an image with a vision model. Only use this tool when the image was NOT already provided in the user's message. Images mentioned in the prompt are automatically visible to you."
+    : "Analyze an image with the configured image model (agents.defaults.imageModel). Provide a prompt and image path or URL.";
+
   return {
     label: "Image",
     name: "image",
-    description:
-      "Analyze an image with the configured image model (agents.defaults.imageModel). Provide a prompt and image path or URL.",
+    description,
     parameters: Type.Object({
       prompt: Type.Optional(Type.String()),
       image: Type.String(),
diff --git a/src/imessage/monitor/monitor-provider.ts b/src/imessage/monitor/monitor-provider.ts
index 4a388d8cb..e94c53a3b 100644
--- a/src/imessage/monitor/monitor-provider.ts
+++ b/src/imessage/monitor/monitor-provider.ts
@@ -307,9 +307,16 @@ export async function monitorIMessageProvider(opts: MonitorIMessageOpts = {}): P
     const mentionRegexes = buildMentionRegexes(cfg, route.agentId);
     const messageText = (message.text ?? "").trim();
     const attachments = includeAttachments ? (message.attachments ?? []) : [];
-    const firstAttachment = attachments?.find((entry) => entry?.original_path && !entry?.missing);
+    // Filter to valid attachments with paths
+    const validAttachments = attachments.filter(
+      (entry) => entry?.original_path && !entry?.missing,
+    );
+    const firstAttachment = validAttachments[0];
     const mediaPath = firstAttachment?.original_path ?? undefined;
     const mediaType = firstAttachment?.mime_type ?? undefined;
+    // Build arrays for all attachments (for multi-image support)
+    const mediaPaths = validAttachments.map((a) => a.original_path).filter(Boolean) as string[];
+    const mediaTypes = validAttachments.map((a) => a.mime_type ?? undefined);
     const kind = mediaKindFromMime(mediaType ?? undefined);
     const placeholder = kind ? `<media:${kind}>` : attachments?.length ? "<media:attachment>" : "";
     const bodyText = messageText || placeholder;
@@ -445,6 +452,9 @@ export async function monitorIMessageProvider(opts: MonitorIMessageOpts = {}): P
       MediaPath: mediaPath,
       MediaType: mediaType,
       MediaUrl: mediaPath,
+      MediaPaths: mediaPaths.length > 0 ? mediaPaths : undefined,
+      MediaTypes: mediaTypes.length > 0 ? mediaTypes : undefined,
+      MediaUrls: mediaPaths.length > 0 ? mediaPaths : undefined,
       MediaRemoteHost: remoteHost,
       WasMentioned: effectiveWasMentioned,
       CommandAuthorized: commandAuthorized,
diff --git a/src/media/image-ops.ts b/src/media/image-ops.ts
index 904b87a6d..e97e14b1c 100644
--- a/src/media/image-ops.ts
+++ b/src/media/image-ops.ts
@@ -28,6 +28,98 @@ async function loadSharp(): Promise<(buffer: Buffer) => ReturnType<Sharp>> {
   return (buffer) => sharp(buffer, { failOnError: false });
 }
 
+/**
+ * Reads EXIF orientation from JPEG buffer.
+ * Returns orientation value 1-8, or null if not found/not JPEG.
+ *
+ * EXIF orientation values:
+ * 1 = Normal, 2 = Flip H, 3 = Rotate 180, 4 = Flip V,
+ * 5 = Rotate 270 CW + Flip H, 6 = Rotate 90 CW, 7 = Rotate 90 CW + Flip H, 8 = Rotate 270 CW
+ */
+function readJpegExifOrientation(buffer: Buffer): number | null {
+  // Check JPEG magic bytes
+  if (buffer.length < 2 || buffer[0] !== 0xff || buffer[1] !== 0xd8) {
+    return null;
+  }
+
+  let offset = 2;
+  while (offset < buffer.length - 4) {
+    // Look for marker
+    if (buffer[offset] !== 0xff) {
+      offset++;
+      continue;
+    }
+
+    const marker = buffer[offset + 1];
+    // Skip padding FF bytes
+    if (marker === 0xff) {
+      offset++;
+      continue;
+    }
+
+    // APP1 marker (EXIF)
+    if (marker === 0xe1) {
+      const segmentLength = buffer.readUInt16BE(offset + 2);
+      const exifStart = offset + 4;
+
+      // Check for "Exif\0\0" header
+      if (
+        buffer.length > exifStart + 6 &&
+        buffer.toString("ascii", exifStart, exifStart + 4) === "Exif" &&
+        buffer[exifStart + 4] === 0 &&
+        buffer[exifStart + 5] === 0
+      ) {
+        const tiffStart = exifStart + 6;
+        if (buffer.length < tiffStart + 8) return null;
+
+        // Check byte order (II = little-endian, MM = big-endian)
+        const byteOrder = buffer.toString("ascii", tiffStart, tiffStart + 2);
+        const isLittleEndian = byteOrder === "II";
+
+        const readU16 = (pos: number) =>
+          isLittleEndian ? buffer.readUInt16LE(pos) : buffer.readUInt16BE(pos);
+        const readU32 = (pos: number) =>
+          isLittleEndian ? buffer.readUInt32LE(pos) : buffer.readUInt32BE(pos);
+
+        // Read IFD0 offset
+        const ifd0Offset = readU32(tiffStart + 4);
+        const ifd0Start = tiffStart + ifd0Offset;
+        if (buffer.length < ifd0Start + 2) return null;
+
+        const numEntries = readU16(ifd0Start);
+        for (let i = 0; i < numEntries; i++) {
+          const entryOffset = ifd0Start + 2 + i * 12;
+          if (buffer.length < entryOffset + 12) break;
+
+          const tag = readU16(entryOffset);
+          // Orientation tag = 0x0112
+          if (tag === 0x0112) {
+            const value = readU16(entryOffset + 8);
+            return value >= 1 && value <= 8 ? value : null;
+          }
+        }
+      }
+      return null;
+    }
+
+    // Skip other segments
+    if (marker >= 0xe0 && marker <= 0xef) {
+      const segmentLength = buffer.readUInt16BE(offset + 2);
+      offset += 2 + segmentLength;
+      continue;
+    }
+
+    // SOF, SOS, or other marker - stop searching
+    if (marker === 0xc0 || marker === 0xda) {
+      break;
+    }
+
+    offset++;
+  }
+
+  return null;
+}
+
 async function withTempDir<T>(fn: (dir: string) => Promise<T>): Promise<T> {
   const dir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-img-"));
   try {
@@ -108,6 +200,81 @@ export async function getImageMetadata(buffer: Buffer): Promise<ImageMetadata |
   }
 }
 
+/**
+ * Applies rotation/flip to image buffer using sips based on EXIF orientation.
+ */
+async function sipsApplyOrientation(buffer: Buffer, orientation: number): Promise<Buffer> {
+  // Map EXIF orientation to sips operations
+  // sips -r rotates clockwise, -f flips (horizontal/vertical)
+  const ops: string[] = [];
+  switch (orientation) {
+    case 2: // Flip horizontal
+      ops.push("-f", "horizontal");
+      break;
+    case 3: // Rotate 180
+      ops.push("-r", "180");
+      break;
+    case 4: // Flip vertical
+      ops.push("-f", "vertical");
+      break;
+    case 5: // Rotate 270 CW + flip horizontal
+      ops.push("-r", "270", "-f", "horizontal");
+      break;
+    case 6: // Rotate 90 CW
+      ops.push("-r", "90");
+      break;
+    case 7: // Rotate 90 CW + flip horizontal
+      ops.push("-r", "90", "-f", "horizontal");
+      break;
+    case 8: // Rotate 270 CW
+      ops.push("-r", "270");
+      break;
+    default:
+      // Orientation 1 or unknown - no change needed
+      return buffer;
+  }
+
+  return await withTempDir(async (dir) => {
+    const input = path.join(dir, "in.jpg");
+    const output = path.join(dir, "out.jpg");
+    await fs.writeFile(input, buffer);
+    await runExec(
+      "/usr/bin/sips",
+      [...ops, input, "--out", output],
+      { timeoutMs: 20_000, maxBuffer: 1024 * 1024 },
+    );
+    return await fs.readFile(output);
+  });
+}
+
+/**
+ * Normalizes EXIF orientation in an image buffer.
+ * Returns the buffer with correct pixel orientation (rotated if needed).
+ * Falls back to original buffer if normalization fails.
+ */
+export async function normalizeExifOrientation(buffer: Buffer): Promise<Buffer> {
+  if (prefersSips()) {
+    try {
+      const orientation = readJpegExifOrientation(buffer);
+      if (!orientation || orientation === 1) {
+        return buffer; // No rotation needed
+      }
+      return await sipsApplyOrientation(buffer, orientation);
+    } catch {
+      return buffer;
+    }
+  }
+
+  try {
+    const sharp = await loadSharp();
+    // .rotate() with no args auto-rotates based on EXIF orientation
+    return await sharp(buffer).rotate().toBuffer();
+  } catch {
+    // Sharp not available or failed - return original buffer
+    return buffer;
+  }
+}
+
 export async function resizeToJpeg(params: {
   buffer: Buffer;
   maxSide: number;
@@ -115,14 +282,17 @@ export async function resizeToJpeg(params: {
   withoutEnlargement?: boolean;
 }): Promise<Buffer> {
   if (prefersSips()) {
+    // Normalize EXIF orientation BEFORE resizing (sips resize doesn't auto-rotate)
+    const normalized = await normalizeExifOrientationSips(params.buffer);
+
     // Avoid enlarging by checking dimensions first (sips has no withoutEnlargement flag).
     if (params.withoutEnlargement !== false) {
-      const meta = await getImageMetadata(params.buffer);
+      const meta = await getImageMetadata(normalized);
       if (meta) {
         const maxDim = Math.max(meta.width, meta.height);
         if (maxDim > 0 && maxDim <= params.maxSide) {
           return await sipsResizeToJpeg({
-            buffer: params.buffer,
+            buffer: normalized,
             maxSide: maxDim,
             quality: params.quality,
           });
@@ -130,14 +300,16 @@ export async function resizeToJpeg(params: {
       }
     }
     return await sipsResizeToJpeg({
-      buffer: params.buffer,
+      buffer: normalized,
       maxSide: params.maxSide,
       quality: params.quality,
     });
   }
 
   const sharp = await loadSharp();
+  // Use .rotate() BEFORE .resize() to auto-rotate based on EXIF orientation
   return await sharp(params.buffer)
+    .rotate() // Auto-rotate based on EXIF before resizing
     .resize({
       width: params.maxSide,
       height: params.maxSide,
@@ -147,3 +319,19 @@ export async function resizeToJpeg(params: {
     .jpeg({ quality: params.quality, mozjpeg: true })
     .toBuffer();
 }
+
+/**
+ * Internal sips-only EXIF normalization (no sharp fallback).
+ * Used by resizeToJpeg to normalize before sips resize.
+ */
+async function normalizeExifOrientationSips(buffer: Buffer): Promise<Buffer> {
+  try {
+    const orientation = readJpegExifOrientation(buffer);
+    if (!orientation || orientation === 1) {
+      return buffer;
+    }
+    return await sipsApplyOrientation(buffer, orientation);
+  } catch {
+    return buffer;
+  }
+}