diff --git a/cli/src/commands/__tests__/image.test.ts b/cli/src/commands/__tests__/image.test.ts
index 2f5e2b985d..e2050e575e 100644
--- a/cli/src/commands/__tests__/image.test.ts
+++ b/cli/src/commands/__tests__/image.test.ts
@@ -1,26 +1,6 @@
 import { describe, test, expect } from 'bun:test'
 
-/**
- * Tests for the handleImageCommand argument parsing behavior.
- *
- * These tests verify the parsing logic independently of the actual
- * validateAndAddImage implementation by testing the parsing function directly.
- */
-
-// Extract the parsing logic that handleImageCommand uses
-// New simplified implementation: split on whitespace
-function parseImageCommandArgs(args: string): {
-  imagePath: string | null
-  message: string
-} {
-  const [imagePath, ...rest] = args.trim().split(/\s+/)
-
-  if (!imagePath) {
-    return { imagePath: null, message: '' }
-  }
-
-  return { imagePath, message: rest.join(' ') }
-}
+import { parseImageCommandArgs } from '../parse-image-args'
 
 describe('handleImageCommand parsing', () => {
   describe('argument parsing', () => {
@@ -61,9 +41,38 @@ describe('handleImageCommand parsing', () => {
     test('handles multiple spaces between path and message', () => {
       const result = parseImageCommandArgs('./image.png    hello world')
       expect(result.imagePath).toBe('./image.png')
-      // The regex only captures content after the first whitespace group
       expect(result.message).toBe('hello world')
     })
+
+    test('handles double-quoted path with spaces and message', () => {
+      const result = parseImageCommandArgs(
+        '"Screenshot 2026-09-02 at 10.00.00.png" please analyze this',
+      )
+      expect(result.imagePath).toBe('Screenshot 2026-09-02 at 10.00.00.png')
+      expect(result.message).toBe('please analyze this')
+    })
+
+    test('handles single-quoted path with spaces and message', () => {
+      const result = parseImageCommandArgs(
+        "'./Screenshots/My Capture.png' what is in this picture?",
+      )
+      expect(result.imagePath).toBe('./Screenshots/My Capture.png')
+      expect(result.message).toBe('what is in this picture?')
+    })
+
+    test('handles quoted path only without message', () => {
+      const result = parseImageCommandArgs('"my screenshot.png"')
+      expect(result.imagePath).toBe('my screenshot.png')
+      expect(result.message).toBe('')
+    })
+
+    test('handles backslash-escaped spaces in path', () => {
+      const result = parseImageCommandArgs(
+        './My\\ Screenshot.png check this out',
+      )
+      expect(result.imagePath).toBe('./My Screenshot.png')
+      expect(result.message).toBe('check this out')
+    })
   })
 
   describe('invalid input handling', () => {
@@ -95,5 +104,11 @@ describe('handleImageCommand parsing', () => {
       const result = parseImageCommandArgs('~/Downloads/image.png')
       expect(result.imagePath).toBe('~/Downloads/image.png')
     })
+
+    test('handles empty quotes gracefully', () => {
+      const result = parseImageCommandArgs('"" please analyze this')
+      expect(result.imagePath).toBeNull()
+      expect(result.message).toBe('please analyze this')
+    })
   })
 })
diff --git a/cli/src/commands/command-registry.ts b/cli/src/commands/command-registry.ts
index 820df1deca..75ac90d488 100644
--- a/cli/src/commands/command-registry.ts
+++ b/cli/src/commands/command-registry.ts
@@ -453,9 +453,17 @@ const ALL_COMMANDS: CommandDefinition[] = [
 
       // If user provided a path directly, process it immediately
       if (trimmedArgs) {
-        await handleImageCommand(trimmedArgs)
+        const remainingMessage = await handleImageCommand(trimmedArgs)
         params.saveToHistory(params.inputValue.trim())
-        clearInput(params)
+        if (remainingMessage) {
+          params.setInputValue({
+            text: remainingMessage,
+            cursorPosition: remainingMessage.length,
+            lastEditDueToNav: false,
+          })
+        } else {
+          clearInput(params)
+        }
         return
       }
 
diff --git a/cli/src/commands/image.ts b/cli/src/commands/image.ts
index f9a27fd041..86139ca490 100644
--- a/cli/src/commands/image.ts
+++ b/cli/src/commands/image.ts
@@ -1,6 +1,9 @@
+import { parseImageCommandArgs } from './parse-image-args'
 import { getProjectRoot } from '../project-files'
 import { validateAndAddImage } from '../utils/pending-attachments'
 
+export { parseImageCommandArgs }
+
 /**
  * Handle the /image command to attach an image file.
  * Usage: /image <path> [message]
@@ -10,11 +13,11 @@ import { validateAndAddImage } from '../utils/pending-attachments'
  * Errors are shown in the pending images banner with auto-remove.
  */
 export async function handleImageCommand(args: string): Promise<string> {
-  const [imagePath, ...rest] = args.trim().split(/\s+/)
-  
+  const { imagePath, message } = parseImageCommandArgs(args)
+
   if (imagePath) {
     await validateAndAddImage(imagePath, getProjectRoot())
   }
-  
-  return rest.join(' ')
+
+  return message
 }
diff --git a/cli/src/commands/parse-image-args.ts b/cli/src/commands/parse-image-args.ts
new file mode 100644
index 0000000000..cad2ce1c6c
--- /dev/null
+++ b/cli/src/commands/parse-image-args.ts
@@ -0,0 +1,54 @@
+/**
+ * Parse image command arguments into image path and optional accompanying message.
+ * Supports quoted paths ("path with spaces" or 'path with spaces') and backslash-escaped spaces.
+ */
+export function parseImageCommandArgs(args: string): {
+  imagePath: string | null
+  message: string
+} {
+  const trimmed = args.trim()
+  if (!trimmed) {
+    return { imagePath: null, message: '' }
+  }
+
+  const firstChar = trimmed[0]
+  if (firstChar === '"' || firstChar === "'") {
+    const closingQuoteIndex = trimmed.indexOf(firstChar, 1)
+    if (closingQuoteIndex !== -1) {
+      const imagePath = trimmed.slice(1, closingQuoteIndex)
+      const message = trimmed.slice(closingQuoteIndex + 1).trim()
+      return { imagePath: imagePath || null, message }
+    }
+  }
+
+  let i = 0
+  let inEscape = false
+  let pathEnd = -1
+
+  for (; i < trimmed.length; i++) {
+    const char = trimmed[i]
+    if (inEscape) {
+      inEscape = false
+      continue
+    }
+    if (char === '\\') {
+      inEscape = true
+      continue
+    }
+    if (/\s/.test(char)) {
+      pathEnd = i
+      break
+    }
+  }
+
+  if (pathEnd === -1) {
+    const imagePath = trimmed.replace(/\\(\s)/g, '$1')
+    return { imagePath: imagePath || null, message: '' }
+  }
+
+  const rawPath = trimmed.slice(0, pathEnd)
+  const imagePath = rawPath.replace(/\\(\s)/g, '$1')
+  const message = trimmed.slice(pathEnd).trim()
+
+  return { imagePath: imagePath || null, message }
+}