diff --git a/TextGrabber2/Sources/App/App+Detection.swift b/TextGrabber2/Sources/App/App+Detection.swift
index 0ea7ff5..8f3ef04 100644
--- a/TextGrabber2/Sources/App/App+Detection.swift
+++ b/TextGrabber2/Sources/App/App+Detection.swift
@@ -10,7 +10,7 @@ import AppKit
 // MARK: - Text Detecting
 
 extension App {
-  func startDetection(userInitiated: Bool = false) async {
+  func startDetection(userInitiated: Bool = false, allowingFileAccess: Bool = true) async {
     let newCount = NSPasteboard.general.changeCount
     if silentDetectCount == newCount {
       if userInitiated {
@@ -21,6 +21,7 @@ extension App {
       return
     }
 
+    silentDetectCount = nil
     currentResult = nil
     clearMenuItems()
 
@@ -32,11 +33,17 @@ extension App {
     copyAllQuickItem.isHidden = true
     copyAllMenuItem.isEnabled = false
 
-    let image = NSPasteboard.general.image?.cgImage
+    let containsFiles = NSPasteboard.general.containsFileReferences
+    let image = NSPasteboard.general.image(allowingFileAccess: allowingFileAccess)?.cgImage
     let text = NSPasteboard.general.string
 
     if let result = await Recognizer.detect(image: image, level: .accurate) {
       updateResult(result, textCopied: text, in: mainMenu)
+
+      // Skipped or unreadable files must remain eligible for an explicit retry
+      if !containsFiles || image != nil {
+        silentDetectCount = newCount
+      }
     } else {
       Logger.log(.error, "Failed to detect text from image")
     }
@@ -45,8 +52,7 @@ extension App {
       Logger.log(.debug, "Presenting newly detected results")
       presentMainMenu()
     } else {
-      Logger.log(.debug, "Silently detected and cached")
-      silentDetectCount = newCount
+      Logger.log(.debug, "Silent detection finished")
     }
   }
 }
@@ -71,6 +77,7 @@ private extension App {
       return
     }
 
+    clearMenuItems()
     currentResult = resultData
     translateItem.isEnabled = resultData.candidates.hasValue
     quickLookItem.isEnabled = resultData.candidates.hasValue
diff --git a/TextGrabber2/Sources/App/App+Observer.swift b/TextGrabber2/Sources/App/App+Observer.swift
index fa05ba8..69df8ce 100644
--- a/TextGrabber2/Sources/App/App+Observer.swift
+++ b/TextGrabber2/Sources/App/App+Observer.swift
@@ -26,7 +26,7 @@ extension App {
       ContentFilters.processRules(for: pasteboard)
 
       Task {
-        await self?.startDetection()
+        await self?.startDetection(allowingFileAccess: false)
       }
     }
 
diff --git a/TextGrabber2/Sources/App/App.swift b/TextGrabber2/Sources/App/App.swift
index cd5506a..dd65b35 100644
--- a/TextGrabber2/Sources/App/App.swift
+++ b/TextGrabber2/Sources/App/App.swift
@@ -14,7 +14,7 @@ final class App: NSObject, NSApplicationDelegate {
   var copyObserver: Task<Void, Never>?
   var currentResult: Recognizer.ResultData?
   var previewingFileURL: URL?
-  var silentDetectCount = 0
+  var silentDetectCount: Int?
 
   lazy var statusItem: NSStatusItem = {
     let item = NSStatusBar.system.statusItem(withLength: NSStatusItem.variableLength)
diff --git a/TextGrabber2/Sources/Extensions/NSPasteboard+Extension.swift b/TextGrabber2/Sources/Extensions/NSPasteboard+Extension.swift
index 7704ee7..c7f8854 100644
--- a/TextGrabber2/Sources/Extensions/NSPasteboard+Extension.swift
+++ b/TextGrabber2/Sources/Extensions/NSPasteboard+Extension.swift
@@ -27,6 +27,21 @@ extension NSPasteboard {
   }
 
   var image: NSImage? {
+    image(allowingFileAccess: true)
+  }
+
+  var containsFileReferences: Bool {
+    types?.contains {
+      $0 == .fileURL || $0.rawValue == "NSFilenamesPboardType"
+    } ?? false
+  }
+
+  func image(allowingFileAccess: Bool) -> NSImage? {
+    // Check types before requesting data or letting AppKit resolve file references
+    if !allowingFileAccess && containsFileReferences {
+      return nil
+    }
+
     // Copied file
     if let data = data(forType: .fileURL),
        let string = String(data: data, encoding: .utf8),