diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4bd38e3..154f106 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,15 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+### Fixed
+- Fixed overly broad permission error detection that incorrectly reported file I/O errors as screen recording permission issues
+  - File permission errors (e.g., writing to `/System/`) now correctly report as `FILE_IO_ERROR`
+  - Directory not found errors provide clear messages about missing parent directories
+  - Added specific error code checking for ScreenCaptureKit and CoreGraphics APIs
+  - Only errors containing both "permission" and capture-related terms are now considered screen recording issues
+- Enhanced file write error handling with pre-emptive directory checks
+- Added debug logging to permission checker for diagnosing intermittent failures
+
 ## [1.0.0-beta.19] - 2025-06-08
 
 ### Added
diff --git a/peekaboo-cli/Sources/peekaboo/PermissionsChecker.swift b/peekaboo-cli/Sources/peekaboo/PermissionsChecker.swift
index 26fdb16..66d816e 100644
--- a/peekaboo-cli/Sources/peekaboo/PermissionsChecker.swift
+++ b/peekaboo-cli/Sources/peekaboo/PermissionsChecker.swift
@@ -9,6 +9,7 @@ class PermissionsChecker {
         // We check by attempting to get shareable content
         let semaphore = DispatchSemaphore(value: 0)
         var hasPermission = false
+        var capturedError: Error?
 
         Task {
             do {
@@ -17,12 +18,18 @@ class PermissionsChecker {
                 hasPermission = true
             } catch {
                 // If we get an error, we don't have permission
+                capturedError = error
                 hasPermission = false
             }
             semaphore.signal()
         }
 
         semaphore.wait()
+        
+        if let error = capturedError {
+            Logger.shared.debug("Screen recording permission check failed: \(error)")
+        }
+        
         return hasPermission
     }