diff --git a/i18n/en.json b/i18n/en.json
index b475c409b0..6a15967ce6 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -1409,7 +1409,7 @@
     "translation": "Don't have permissions to write to local path specified or other error."
   },
   {
-    "id": "api.file.test_connection.s3.bucked_create.app_error",
+    "id": "api.file.test_connection.s3.bucket_create.app_error",
     "translation": "Unable to create bucket."
   },
   {
@@ -1420,6 +1420,10 @@
     "id": "api.file.test_connection.s3.connection.app_error",
     "translation": "Bad connection to S3 or minio."
   },
+  {
+    "id": "api.file.test_connection.s3.list_objects.app_error",
+    "translation": "Error trying to list objects."
+  },
   {
     "id": "api.file.upload_file.incorrect_channelId.app_error",
     "translation": "Unable to upload the file. Incorrect channel ID: {{.channelId}}"
diff --git a/services/filesstore/s3store.go b/services/filesstore/s3store.go
index 7750dd4a8b..465973adfe 100644
--- a/services/filesstore/s3store.go
+++ b/services/filesstore/s3store.go
@@ -34,6 +34,11 @@ type S3FileBackend struct {
 	trace      bool
 }
 
+const (
+	// This is not exported by minio. See: https://github.com/minio/minio-go/issues/1339
+	bucketNotFound = "NoSuchBucket"
+)
+
 // Similar to s3.New() but allows initialization of signature v2 or signature v4 client.
 // If signV2 input is false, function always returns signature v4.
 //
@@ -73,20 +78,36 @@ func (b *S3FileBackend) TestConnection() *model.AppError {
 		return model.NewAppError("TestFileConnection", "api.file.test_connection.s3.connection.app_error", nil, err.Error(), http.StatusInternalServerError)
 	}
 
-	exists, err := s3Clnt.BucketExists(context.Background(), b.bucket)
-	if err != nil {
-		return model.NewAppError("TestFileConnection", "api.file.test_connection.s3.bucket_exists.app_error", nil, err.Error(), http.StatusInternalServerError)
+	exists := true
+	// If a path prefix is present, we attempt to test the bucket by listing objects under the path
+	// and just checking the first response. This is because the BucketExists call is only at a bucket level
+	// and sometimes the user might only be allowed access to the specified path prefix.
+	if b.pathPrefix != "" {
+		obj := <-s3Clnt.ListObjects(context.Background(), b.bucket, s3.ListObjectsOptions{Prefix: b.pathPrefix})
+		if obj.Err != nil {
+			typedErr := s3.ToErrorResponse(obj.Err)
+			if typedErr.Code != bucketNotFound {
+				return model.NewAppError("TestFileConnection", "api.file.test_connection.s3.list_objects.app_error", nil, obj.Err.Error(), http.StatusInternalServerError)
+			}
+			exists = false
+		}
+	} else {
+		exists, err = s3Clnt.BucketExists(context.Background(), b.bucket)
+		if err != nil {
+			return model.NewAppError("TestFileConnection", "api.file.test_connection.s3.bucket_exists.app_error", nil, err.Error(), http.StatusInternalServerError)
+		}
 	}
 
-	if !exists {
+	if exists {
+		mlog.Debug("Connection to S3 or minio is good. Bucket exists.")
+	} else {
 		mlog.Warn("Bucket specified does not exist. Attempting to create...")
 		err := s3Clnt.MakeBucket(context.Background(), b.bucket, s3.MakeBucketOptions{Region: b.region})
 		if err != nil {
-			mlog.Error("Unable to create bucket.")
-			return model.NewAppError("TestFileConnection", "api.file.test_connection.s3.bucked_create.app_error", nil, err.Error(), http.StatusInternalServerError)
+			return model.NewAppError("TestFileConnection", "api.file.test_connection.s3.bucket_create.app_error", nil, err.Error(), http.StatusInternalServerError)
 		}
 	}
-	mlog.Debug("Connection to S3 or minio is good. Bucket exists.")
+
 	return nil
 }