diff --git a/internal/fsext/fileutil.go b/internal/fsext/fileutil.go
index aee72bb1a5fa1affbd36e86e73f02d8407fa982b..d0d47eaed4aa946db50a9c5c4a50a0b214e92b0b 100644
--- a/internal/fsext/fileutil.go
+++ b/internal/fsext/fileutil.go
@@ -262,3 +262,23 @@ func DirTrim(pwd string, lim int) string {
 	out = filepath.Join("~", out)
 	return out
 }
+
+// PathOrPrefix returns the prefix if the path starts with it, or falls back to
+// the path otherwise.
+func PathOrPrefix(path, prefix string) string {
+	if HasPrefix(path, prefix) {
+		return prefix
+	}
+	return path
+}
+
+// HasPrefix checks if the given path starts with the specified prefix.
+func HasPrefix(path, prefix string) bool {
+	if abs, err := filepath.Abs(path); err == nil {
+		path = abs
+	}
+	if abs, err := filepath.Abs(prefix); err == nil {
+		prefix = abs
+	}
+	return strings.HasPrefix(path, prefix)
+}
diff --git a/internal/llm/tools/edit.go b/internal/llm/tools/edit.go
index 36af176af8d8e531e30707dffad33b66ebb8d33b..fd9ed81d55bc96e7b7767adad2f1186d88d97023 100644
--- a/internal/llm/tools/edit.go
+++ b/internal/llm/tools/edit.go
@@ -11,6 +11,7 @@ import (
 	"time"
 
 	"github.com/charmbracelet/crush/internal/diff"
+	"github.com/charmbracelet/crush/internal/fsext"
 	"github.com/charmbracelet/crush/internal/history"
 
 	"github.com/charmbracelet/crush/internal/lsp"
@@ -215,14 +216,10 @@ func (e *editTool) createNewFile(ctx context.Context, filePath, content string,
 		content,
 		strings.TrimPrefix(filePath, e.workingDir),
 	)
-	permissionPath := filePath
-	if strings.HasPrefix(filePath, e.workingDir) {
-		permissionPath = e.workingDir
-	}
 	p := e.permissions.Request(
 		permission.CreatePermissionRequest{
 			SessionID:   sessionID,
-			Path:        permissionPath,
+			Path:        fsext.PathOrPrefix(filePath, e.workingDir),
 			ToolCallID:  call.ID,
 			ToolName:    EditToolName,
 			Action:      "write",
@@ -340,15 +337,10 @@ func (e *editTool) deleteContent(ctx context.Context, filePath, oldString string
 		strings.TrimPrefix(filePath, e.workingDir),
 	)
 
-	permissionPath := filePath
-	if strings.HasPrefix(filePath, e.workingDir) {
-		permissionPath = e.workingDir
-	}
-
 	p := e.permissions.Request(
 		permission.CreatePermissionRequest{
 			SessionID:   sessionID,
-			Path:        permissionPath,
+			Path:        fsext.PathOrPrefix(filePath, e.workingDir),
 			ToolCallID:  call.ID,
 			ToolName:    EditToolName,
 			Action:      "write",
@@ -476,14 +468,10 @@ func (e *editTool) replaceContent(ctx context.Context, filePath, oldString, newS
 		strings.TrimPrefix(filePath, e.workingDir),
 	)
 
-	permissionPath := filePath
-	if strings.HasPrefix(filePath, e.workingDir) {
-		permissionPath = e.workingDir
-	}
 	p := e.permissions.Request(
 		permission.CreatePermissionRequest{
 			SessionID:   sessionID,
-			Path:        permissionPath,
+			Path:        fsext.PathOrPrefix(filePath, e.workingDir),
 			ToolCallID:  call.ID,
 			ToolName:    EditToolName,
 			Action:      "write",
diff --git a/internal/llm/tools/multiedit.go b/internal/llm/tools/multiedit.go
index 86a734611de35eb9beda7b78b6af338a985c7be9..271603a5b0f97b78bb7dbe53b93a060cff48b9cc 100644
--- a/internal/llm/tools/multiedit.go
+++ b/internal/llm/tools/multiedit.go
@@ -11,6 +11,7 @@ import (
 	"time"
 
 	"github.com/charmbracelet/crush/internal/diff"
+	"github.com/charmbracelet/crush/internal/fsext"
 	"github.com/charmbracelet/crush/internal/history"
 	"github.com/charmbracelet/crush/internal/lsp"
 	"github.com/charmbracelet/crush/internal/permission"
@@ -250,14 +251,9 @@ func (m *multiEditTool) processMultiEditWithCreation(ctx context.Context, params
 	// Check permissions
 	_, additions, removals := diff.GenerateDiff("", currentContent, strings.TrimPrefix(params.FilePath, m.workingDir))
 
-	permissionPath := params.FilePath
-	if strings.HasPrefix(params.FilePath, m.workingDir) {
-		permissionPath = m.workingDir
-	}
-
 	p := m.permissions.Request(permission.CreatePermissionRequest{
 		SessionID:   sessionID,
-		Path:        permissionPath,
+		Path:        fsext.PathOrPrefix(params.FilePath, m.workingDir),
 		ToolCallID:  call.ID,
 		ToolName:    MultiEditToolName,
 		Action:      "write",
@@ -364,13 +360,9 @@ func (m *multiEditTool) processMultiEditExistingFile(ctx context.Context, params
 
 	// Generate diff and check permissions
 	_, additions, removals := diff.GenerateDiff(oldContent, currentContent, strings.TrimPrefix(params.FilePath, m.workingDir))
-	permissionPath := params.FilePath
-	if strings.HasPrefix(params.FilePath, m.workingDir) {
-		permissionPath = m.workingDir
-	}
 	p := m.permissions.Request(permission.CreatePermissionRequest{
 		SessionID:   sessionID,
-		Path:        permissionPath,
+		Path:        fsext.PathOrPrefix(params.FilePath, m.workingDir),
 		ToolCallID:  call.ID,
 		ToolName:    MultiEditToolName,
 		Action:      "write",
diff --git a/internal/llm/tools/write.go b/internal/llm/tools/write.go
index da8722d5646a058b9241fbe487b0ecc6c95d82ae..d719337a971cb09babd47753444d761586806fdd 100644
--- a/internal/llm/tools/write.go
+++ b/internal/llm/tools/write.go
@@ -11,6 +11,7 @@ import (
 	"time"
 
 	"github.com/charmbracelet/crush/internal/diff"
+	"github.com/charmbracelet/crush/internal/fsext"
 	"github.com/charmbracelet/crush/internal/history"
 
 	"github.com/charmbracelet/crush/internal/lsp"
@@ -172,15 +173,10 @@ func (w *writeTool) Run(ctx context.Context, call ToolCall) (ToolResponse, error
 		strings.TrimPrefix(filePath, w.workingDir),
 	)
 
-	permissionPath := filePath
-	if strings.HasPrefix(filePath, w.workingDir) {
-		permissionPath = w.workingDir
-	}
-
 	p := w.permissions.Request(
 		permission.CreatePermissionRequest{
 			SessionID:   sessionID,
-			Path:        permissionPath,
+			Path:        fsext.PathOrPrefix(filePath, w.workingDir),
 			ToolCallID:  call.ID,
 			ToolName:    WriteToolName,
 			Action:      "write",