diff --git a/dhavnii/Features/Clipboard/ClipboardManager.swift b/dhavnii/Features/Clipboard/ClipboardManager.swift
index 73801e8..f408d58 100644
--- a/dhavnii/Features/Clipboard/ClipboardManager.swift
+++ b/dhavnii/Features/Clipboard/ClipboardManager.swift
@@ -11,6 +11,26 @@ import Carbon
 
 /// Manages clipboard operations and auto-pasting
 class ClipboardManager {
+    private let autoPasteRetryDelay: TimeInterval = 0.12
+    private let autoPasteMaxAttempts = 10
+    private var autoPasteToken = UUID()
+
+    private struct FocusedElementState {
+        let bundleIdentifier: String
+        let role: String?
+        let isEditable: Bool
+
+        var isValidPasteTarget: Bool {
+            switch role {
+            case "AXTextField", "AXTextArea", "AXComboBox", "AXSearchField", "AXStaticText":
+                return true
+            case "AXWebArea", "AXGroup", "AXScrollArea":
+                return isEditable
+            default:
+                return false
+            }
+        }
+    }
     
     /// Copy text to the system clipboard
     func copyToClipboard(_ text: String) {
@@ -19,32 +39,9 @@ class ClipboardManager {
         pasteboard.setString(text, forType: .string)
     }
     
-    /// Check if a text input field is currently focused
-    func isTextFieldFocused() -> Bool {
-        // Use Accessibility API to check if focused element is a text field
-        guard let focusedApp = NSWorkspace.shared.frontmostApplication else {
-            return false
-        }
-        
-        let appElement = AXUIElementCreateApplication(focusedApp.processIdentifier)
-        
-        var focusedElement: CFTypeRef?
-        let result = AXUIElementCopyAttributeValue(appElement, kAXFocusedUIElementAttribute as CFString, &focusedElement)
-        
-        guard result == .success, let element = focusedElement else {
-            return false
-        }
-        
-        var role: CFTypeRef?
-        AXUIElementCopyAttributeValue(element as! AXUIElement, kAXRoleAttribute as CFString, &role)
-        
-        if let roleString = role as? String {
-            // Broaden supported roles to include web areas and editors (VS Code, Chrome, etc.)
-            let textRoles = ["AXTextField", "AXTextArea", "AXComboBox", "AXSearchField", "AXWebArea", "AXGroup", "AXStaticText"]
-            return textRoles.contains(roleString)
-        }
-        
-        return false
+    /// Check if the focused element can safely receive an auto-paste event
+    func isValidPasteTargetFocused() -> Bool {
+        focusedElementState()?.isValidPasteTarget ?? false
     }
     
     /// Simulate Cmd+V to paste
@@ -67,6 +64,9 @@ class ClipboardManager {
         // Always copy to clipboard (mandatory)
         copyToClipboard(text)
 
+        let token = UUID()
+        autoPasteToken = token
+
         let hasAccessibilityPermission = AXIsProcessTrusted()
 
         let frontmostBundleIdentifier = NSWorkspace.shared.frontmostApplication?.bundleIdentifier ?? "unknown"
@@ -84,9 +84,80 @@ class ClipboardManager {
             NSApp.hide(nil)
         }
 
-        // Delay to allow focus to settle/switch back
-        DispatchQueue.main.asyncAfter(deadline: .now() + 0.25) { [weak self] in
-            self?.simulatePaste()
+        // Wait for focus to return to a valid text target before posting Cmd+V.
+        attemptPasteWhenReady(remainingAttempts: autoPasteMaxAttempts, token: token)
+    }
+
+    private func attemptPasteWhenReady(remainingAttempts: Int, token: UUID) {
+        guard token == autoPasteToken else {
+            print("⚠️ Auto-paste cancelled: stale request")
+            return
+        }
+
+        guard remainingAttempts > 0 else {
+            let frontmostBundleIdentifier =
+                NSWorkspace.shared.frontmostApplication?.bundleIdentifier ?? "unknown"
+            let role = focusedElementState()?.role ?? "unknown"
+            print(
+                "⚠️ Auto-paste skipped: no editable target became ready, frontmostApp=\(frontmostBundleIdentifier), role=\(role)"
+            )
+            return
+        }
+
+        if let focusedElement = focusedElementState(),
+           focusedElement.bundleIdentifier != Bundle.main.bundleIdentifier,
+           focusedElement.isValidPasteTarget
+        {
+            guard token == autoPasteToken else {
+                print("⚠️ Auto-paste cancelled before paste: stale request")
+                return
+            }
+            print(
+                "✅ Auto-paste target ready: frontmostApp=\(focusedElement.bundleIdentifier), role=\(focusedElement.role ?? "unknown"), editable=\(focusedElement.isEditable)"
+            )
+            simulatePaste()
+            return
+        }
+
+        DispatchQueue.main.asyncAfter(deadline: .now() + autoPasteRetryDelay) { [weak self] in
+            self?.attemptPasteWhenReady(remainingAttempts: remainingAttempts - 1, token: token)
         }
     }
+
+    private func focusedElementState() -> FocusedElementState? {
+        guard let focusedApp = NSWorkspace.shared.frontmostApplication else {
+            return nil
+        }
+
+        let appElement = AXUIElementCreateApplication(focusedApp.processIdentifier)
+
+        var focusedElement: CFTypeRef?
+        let result = AXUIElementCopyAttributeValue(
+            appElement,
+            kAXFocusedUIElementAttribute as CFString,
+            &focusedElement
+        )
+
+        guard result == .success, let element = focusedElement else {
+            return FocusedElementState(
+                bundleIdentifier: focusedApp.bundleIdentifier ?? "unknown",
+                role: nil,
+                isEditable: false
+            )
+        }
+
+        let axElement = unsafeBitCast(element, to: AXUIElement.self)
+
+        var roleValue: CFTypeRef?
+        AXUIElementCopyAttributeValue(axElement, kAXRoleAttribute as CFString, &roleValue)
+
+        var editableValue: CFTypeRef?
+        AXUIElementCopyAttributeValue(axElement, "AXEditable" as CFString, &editableValue)
+
+        return FocusedElementState(
+            bundleIdentifier: focusedApp.bundleIdentifier ?? "unknown",
+            role: roleValue as? String,
+            isEditable: editableValue as? Bool ?? false
+        )
+    }
 }