diff --git a/internal/myks/sync.go b/internal/myks/sync.go
index b01805db..869b6ff9 100644
--- a/internal/myks/sync.go
+++ b/internal/myks/sync.go
@@ -121,8 +121,7 @@ func (a Application) cleanupVendorDir(vendorDir, vendirConfigFile string) error
 	for _, dir := range config["directories"].([]interface{}) {
 		dirMap := dir.(map[string]interface{})
 		path := dirMap["path"].(string)
-		path = strings.TrimSuffix(path, string(filepath.Separator))
-		dirs = append(dirs, path+string(filepath.Separator))
+		dirs = append(dirs, filepath.Clean(path)+string(filepath.Separator))
 	}
 
 	log.Debug().Strs("managed dirs", dirs).Msg("")
diff --git a/internal/myks/sync_test.go b/internal/myks/sync_test.go
index 7a64ab09..e6ae1be5 100644
--- a/internal/myks/sync_test.go
+++ b/internal/myks/sync_test.go
@@ -104,6 +104,31 @@ func Test_cleanupVendorDir(t *testing.T) {
 			},
 			wantDirs: []string{"charts/httpbingo2"},
 		},
+		{
+			name: "weird-paths",
+			vendirYaml: "directories:\n" +
+				"  - path: charts/httpbingo\n" +
+				"  - path: charts/httpbingo1/\n" +
+				"  - path: charts/httpbingo2//\n" +
+				"  - path: charts//httpbingo22//\n" +
+				"  - path: charts/../httpbingo69\n",
+			createDirs: []string{
+				"charts/httpbingo",
+				"charts/httpbingo1",
+				"charts/httpbingo2",
+				"charts/httpbingo22",
+				"httpbingo69",
+				"charts/trash",
+				"charts/trash1",
+			},
+			wantDirs: []string{
+				"charts/httpbingo",
+				"charts/httpbingo1",
+				"charts/httpbingo2",
+				"charts/httpbingo22",
+				"httpbingo69",
+			},
+		},
 	}
 
 	for _, tt := range tests {