diff --git a/internal/executor/executor.go b/internal/executor/executor.go
index 3d6c4487..c516b22f 100644
--- a/internal/executor/executor.go
+++ b/internal/executor/executor.go
@@ -915,7 +915,7 @@ func (e *Executor) executeTask(ctx context.Context, task *db.Task) {
 		// This is important when attachments are added after the initial run or when resuming
 		feedbackWithAttachments := retryFeedback
 		if len(attachmentPaths) > 0 {
-			feedbackWithAttachments = retryFeedback + "\n" + e.getAttachmentsSection(task.ID, attachmentPaths)
+			feedbackWithAttachments = retryFeedback + "\n" + e.getAttachmentsSection(task.ID, attachmentPaths, workDir)
 		}
 		e.logLine(task.ID, "system", fmt.Sprintf("Resuming previous session with feedback (executor: %s)", executorName))
 		execResult := taskExecutor.Resume(taskCtx, task, workDir, prompt, feedbackWithAttachments)
@@ -1094,7 +1094,9 @@ func (e *Executor) prepareAttachments(taskID int64, worktreePath string) ([]stri
 }
 
 // getAttachmentsSection returns a prompt section describing attachments.
-func (e *Executor) getAttachmentsSection(taskID int64, paths []string) string {
+// The worktreePath parameter is used to convert absolute paths to relative paths
+// so they match the permission pattern Read(.claude/attachments/**).
+func (e *Executor) getAttachmentsSection(taskID int64, paths []string, worktreePath string) string {
 	if len(paths) == 0 {
 		return ""
 	}
@@ -1103,7 +1105,13 @@ func (e *Executor) getAttachmentsSection(taskID int64, paths []string) string {
 	section.WriteString("\n## Attachments\n\n")
 	section.WriteString("The following files are attached to this task:\n")
 	for _, p := range paths {
-		section.WriteString(fmt.Sprintf("- %s\n", p))
+		// Convert absolute paths to relative paths so they match permission patterns
+		relPath := p
+		if worktreePath != "" && strings.HasPrefix(p, worktreePath) {
+			relPath = strings.TrimPrefix(p, worktreePath)
+			relPath = strings.TrimPrefix(relPath, string(filepath.Separator))
+		}
+		section.WriteString(fmt.Sprintf("- %s\n", relPath))
 	}
 	section.WriteString("\nYou can read these files using the Read tool.\n\n")
 	return section.String()
@@ -1134,8 +1142,8 @@ func (e *Executor) buildPrompt(task *db.Task, attachmentPaths []string) string {
 	// Check for conversation history (from previous runs/retries)
 	conversationHistory := e.getConversationHistory(task.ID)
 
-	// Get attachments section
-	attachments := e.getAttachmentsSection(task.ID, attachmentPaths)
+	// Get attachments section (use relative paths to match permission patterns)
+	attachments := e.getAttachmentsSection(task.ID, attachmentPaths, task.WorktreePath)
 
 	// Look up task type instructions from database
 	if task.Type != "" {
diff --git a/internal/executor/executor_test.go b/internal/executor/executor_test.go
index 80d2a2a0..5a500f30 100644
--- a/internal/executor/executor_test.go
+++ b/internal/executor/executor_test.go
@@ -265,9 +265,10 @@ func TestAttachmentsInPrompt(t *testing.T) {
 		}
 	})
 
-	t.Run("getAttachmentsSection uses Read tool", func(t *testing.T) {
+	t.Run("getAttachmentsSection uses Read tool with relative paths", func(t *testing.T) {
+		worktreePath := "/worktree"
 		paths := []string{"/worktree/.claude/attachments/notes.txt", "/worktree/.claude/attachments/data.json"}
-		section := exec.getAttachmentsSection(task.ID, paths)
+		section := exec.getAttachmentsSection(task.ID, paths, worktreePath)
 
 		if !strings.Contains(section, "## Attachments") {
 			t.Error("section should contain Attachments header")
@@ -278,13 +279,19 @@ func TestAttachmentsInPrompt(t *testing.T) {
 		if strings.Contains(section, "View tool") {
 			t.Error("section should NOT mention View tool")
 		}
-		if !strings.Contains(section, "/worktree/.claude/attachments/notes.txt") {
-			t.Error("section should contain file path")
+		// Paths should be relative, not absolute
+		if !strings.Contains(section, ".claude/attachments/notes.txt") {
+			t.Error("section should contain relative file path")
+		}
+		if strings.Contains(section, "/worktree/.claude/attachments/notes.txt") {
+			t.Error("section should NOT contain absolute file path")
 		}
 	})
 
 	t.Run("buildPrompt includes attachments section", func(t *testing.T) {
 		worktreePath := t.TempDir()
+		// Set task's WorktreePath so buildPrompt can convert to relative paths
+		task.WorktreePath = worktreePath
 		paths, cleanup := exec.prepareAttachments(task.ID, worktreePath)
 		defer cleanup()
 
@@ -296,6 +303,10 @@ func TestAttachmentsInPrompt(t *testing.T) {
 		if !strings.Contains(prompt, "Read tool") {
 			t.Error("prompt should mention Read tool")
 		}
+		// Verify paths are relative in the prompt
+		if !strings.Contains(prompt, ".claude/attachments/") {
+			t.Error("prompt should contain relative attachment paths")
+		}
 	})
 
 	t.Run("retry feedback includes attachments when present", func(t *testing.T) {
@@ -307,7 +318,7 @@ func TestAttachmentsInPrompt(t *testing.T) {
 		retryFeedback := "Please fix the bug"
 		feedbackWithAttachments := retryFeedback
 		if len(paths) > 0 {
-			feedbackWithAttachments = retryFeedback + "\n" + exec.getAttachmentsSection(task.ID, paths)
+			feedbackWithAttachments = retryFeedback + "\n" + exec.getAttachmentsSection(task.ID, paths, worktreePath)
 		}
 
 		// Verify attachments are included in the retry feedback
@@ -320,6 +331,10 @@ func TestAttachmentsInPrompt(t *testing.T) {
 		if !strings.Contains(feedbackWithAttachments, "Please fix the bug") {
 			t.Error("retry feedback should still contain original feedback")
 		}
+		// Verify paths are relative
+		if !strings.Contains(feedbackWithAttachments, ".claude/attachments/") {
+			t.Error("retry feedback should contain relative attachment paths")
+		}
 	})
 }