diff --git a/pkg/compose/watch.go b/pkg/compose/watch.go
index 72f329a6252..fd8a61ebd4f 100644
--- a/pkg/compose/watch.go
+++ b/pkg/compose/watch.go
@@ -353,8 +353,11 @@ func loadDevelopmentConfig(service types.ServiceConfig, project *types.Project)
 
 func checkIfPathAlreadyBindMounted(watchPath string, volumes []types.ServiceVolumeConfig) bool {
 	for _, volume := range volumes {
-		if volume.Bind != nil && strings.HasPrefix(watchPath, volume.Source) {
-			return true
+		if volume.Bind != nil {
+			relPath, err := filepath.Rel(volume.Source, watchPath)
+			if err == nil && !strings.HasPrefix(relPath, "..") {
+				return true
+			}
 		}
 	}
 	return false
diff --git a/pkg/e2e/fixtures/watch/compose.yaml b/pkg/e2e/fixtures/watch/compose.yaml
index 5c26ee0fdb7..7e5e0d28bf4 100644
--- a/pkg/e2e/fixtures/watch/compose.yaml
+++ b/pkg/e2e/fixtures/watch/compose.yaml
@@ -37,4 +37,7 @@ services:
         RUN mkdir -p /app/config
     init: true
     command: sleep infinity
+    volumes:
+      - ./dat:/app/dat
+      - ./data-logs:/app/data-logs
     develop: *x-dev
diff --git a/pkg/e2e/fixtures/watch/dat/meow.dat b/pkg/e2e/fixtures/watch/dat/meow.dat
new file mode 100644
index 00000000000..0dd3d19a01d
--- /dev/null
+++ b/pkg/e2e/fixtures/watch/dat/meow.dat
@@ -0,0 +1 @@
+i am a wannabe cat
diff --git a/pkg/e2e/fixtures/watch/data-logs/server.log b/pkg/e2e/fixtures/watch/data-logs/server.log
new file mode 100644
index 00000000000..b6b65a681d9
--- /dev/null
+++ b/pkg/e2e/fixtures/watch/data-logs/server.log
@@ -0,0 +1 @@
+[INFO] Server started successfully on port 8080