diff --git a/util/webhook/webhook.go b/util/webhook/webhook.go
index 2d4dcf39367e8..a4aefd4dc5796 100644
--- a/util/webhook/webhook.go
+++ b/util/webhook/webhook.go
@@ -337,8 +337,13 @@ func appFilesHaveChanged(app *v1alpha1.Application, changedFiles []string) bool
 		f = ensureAbsPath(f)
 		for _, item := range refreshPaths {
 			item = ensureAbsPath(item)
-
-			if _, err := security.EnforceToCurrentRoot(item, f); err == nil {
+			changed := false
+			if f == item {
+				changed = true
+			} else if _, err := security.EnforceToCurrentRoot(item, f); err == nil {
+				changed = true
+			}
+			if changed {
 				log.WithField("application", app.Name).Debugf("Application uses files that have changed")
 				return true
 			}
diff --git a/util/webhook/webhook_test.go b/util/webhook/webhook_test.go
index 5ee3122b33e62..1f8c65fc50ceb 100644
--- a/util/webhook/webhook_test.go
+++ b/util/webhook/webhook_test.go
@@ -220,6 +220,12 @@ func Test_getAppRefreshPrefix(t *testing.T) {
 		{"absolute path - not matching", getApp("/source/path1", "source/path"), []string{"source/path/my-deployment.yaml"}, false},
 		{"two relative paths - matching", getApp(".;../shared", "my-app"), []string{"shared/my-deployment.yaml"}, true},
 		{"two relative paths - not matching", getApp(".;../shared", "my-app"), []string{"README.md"}, false},
+		{"file relative path - matching", getApp("./my-deployment.yaml", "source/path"), []string{"source/path/my-deployment.yaml"}, true},
+		{"file relative path - not matching", getApp("./my-deployment.yaml", "source/path"), []string{"README.md"}, false},
+		{"file absolute path - matching", getApp("/source/path/my-deployment.yaml", "source/path"), []string{"source/path/my-deployment.yaml"}, true},
+		{"file absolute path - not matching", getApp("/source/path1/README.md", "source/path"), []string{"source/path/my-deployment.yaml"}, false},
+		{"file two relative paths - matching", getApp("./README.md;../shared/my-deployment.yaml", "my-app"), []string{"shared/my-deployment.yaml"}, true},
+		{"file two relative paths - not matching", getApp(".README.md;../shared/my-deployment.yaml", "my-app"), []string{"kustomization.yaml"}, false},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {