diff --git a/pkg/logging/logger.go b/pkg/logging/logger.go
index 66eed078ffb..57058f7c9cd 100644
--- a/pkg/logging/logger.go
+++ b/pkg/logging/logger.go
@@ -5,7 +5,7 @@ import (
 	"fmt"
 	"io"
 	"os"
-	"reflect"
+	"regexp"
 	"runtime"
 	"slices"
 	"strings"
@@ -76,9 +76,10 @@ type Fields map[string]interface{}
 
 // logCallerTrimmer is used to trim the caller paths to be relative to the project root
 func logCallerTrimmer(frame *runtime.Frame) (function string, file string) {
-	indexOfModule := strings.Index(strings.ToLower(frame.File), ProjectDirectoryName)
-	if indexOfModule != -1 {
-		file = frame.File[indexOfModule+len(ProjectDirectoryName):]
+	r := regexp.MustCompile(fmt.Sprintf(`.*/([^/]*%s[^/]*)/.*`, ProjectDirectoryName))
+	matches := r.FindStringSubmatch(strings.ToLower(frame.File))
+	if len(matches) > 1 {
+		file = matches[1]
 	} else {
 		file = frame.File
 	}
diff --git a/pkg/logging/logger_test.go b/pkg/logging/logger_test.go
index 7751b24c8eb..471534d52a9 100644
--- a/pkg/logging/logger_test.go
+++ b/pkg/logging/logger_test.go
@@ -6,10 +6,63 @@ import (
 	"io"
 	"os"
 	"path/filepath"
+	"runtime"
 	"testing"
 	"time"
 )
 
+func TestLogCallerTrimmer(t *testing.T) {
+	t.Run("dir name is just lakeFS", func(t *testing.T) {
+		frame := &runtime.Frame{
+			File:     "lakefs/to/main.go",
+			Line:     42,
+			Function: "main.someFunction",
+		}
+		wantFile := "lakefs/to/main.go:42"
+		wantFunction := "main.someFunction"
+		resultFunction, resultFile := logCallerTrimmer(frame)
+		if resultFile != wantFile {
+			t.Fatalf("Result File '%s', should be '%s'", resultFile, wantFile)
+		}
+		if resultFunction != wantFunction {
+			t.Fatalf("Result Function '%s', should be '%s'", resultFunction, wantFunction)
+		}
+	})
+
+	t.Run("dir name is lakeFS-foo", func(t *testing.T) {
+		frame := &runtime.Frame{
+			File:     "lakefs-foo/to/main.go",
+			Line:     42,
+			Function: "main.someFunction",
+		}
+		wantFile := "lakefs-foo/to/main.go:42"
+		wantFunction := "main.someFunction"
+		resultFunction, resultFile := logCallerTrimmer(frame)
+		if resultFile != wantFile {
+			t.Fatalf("Result File '%s', should be '%s'", resultFile, wantFile)
+		}
+		if resultFunction != wantFunction {
+			t.Fatalf("Result Function '%s', should be '%s'", resultFunction, wantFunction)
+		}
+	})
+	t.Run("dir name is just full absolute path", func(t *testing.T) {
+		frame := &runtime.Frame{
+			File:     "Users/Apps/lakeFS-foo/to/main.go",
+			Line:     42,
+			Function: "main.someFunction",
+		}
+		wantFile := "lakeFS-foo/to/main.go:42"
+		wantFunction := "main.someFunction"
+		resultFunction, resultFile := logCallerTrimmer(frame)
+		if resultFile != wantFile {
+			t.Fatalf("Result File '%s', should be '%s'", resultFile, wantFile)
+		}
+		if resultFunction != wantFunction {
+			t.Fatalf("Result Function '%s', should be '%s'", resultFunction, wantFunction)
+		}
+	})
+}
+
 func TestSetOutputs(t *testing.T) {
 	t.Run("default", func(t *testing.T) {
 		currentOut := defaultLogger.Out