diff --git a/apps/dav/lib/Files/Sharing/FilesDropPlugin.php b/apps/dav/lib/Files/Sharing/FilesDropPlugin.php
index b364c4ebbfc10..69328d42272c6 100644
--- a/apps/dav/lib/Files/Sharing/FilesDropPlugin.php
+++ b/apps/dav/lib/Files/Sharing/FilesDropPlugin.php
@@ -62,14 +62,12 @@ public function beforeMethod(RequestInterface $request, ResponseInterface $respo
 		$path = array_pop($path);
 
 		// Extract the attributes for the file request
+		$isFileRequest = false;
 		$attributes = $this->share->getAttributes();
-		if ($attributes === null) {
-			return;
-		}
-
-		// Prepare file request
 		$nickName = $request->getHeader('X-NC-Nickname');
-		$isFileRequest = $attributes->getAttribute('fileRequest', 'enabled') === true;
+		if ($attributes !== null) {
+			$isFileRequest = $attributes->getAttribute('fileRequest', 'enabled') === true;
+		}
 
 		// We need a valid nickname for file requests
 		if ($isFileRequest && ($nickName == null || trim($nickName) === '')) {
diff --git a/build/integration/features/bootstrap/FilesDropContext.php b/build/integration/features/bootstrap/FilesDropContext.php
index b611e55ea0f21..1b9d598645fa1 100644
--- a/build/integration/features/bootstrap/FilesDropContext.php
+++ b/build/integration/features/bootstrap/FilesDropContext.php
@@ -15,7 +15,7 @@ class FilesDropContext implements Context, SnippetAcceptingContext {
 	/**
 	 * @When Dropping file :path with :content
 	 */
-	public function droppingFileWith($path, $content) {
+	public function droppingFileWith($path, $content, $nickName = null) {
 		$client = new Client();
 		$options = [];
 		if (count($this->lastShareData->data->element) > 0) {
@@ -25,11 +25,16 @@ public function droppingFileWith($path, $content) {
 		}
 
 		$base = substr($this->baseUrl, 0, -4);
-		$fullUrl = $base . "/public.php/dav/files/$token/$path";
+		$fullUrl = str_replace('//', '/', $base . "/public.php/dav/files/$token/$path");
 
 		$options['headers'] = [
 			'X-REQUESTED-WITH' => 'XMLHttpRequest'
 		];
+
+		if ($nickName) {
+			$options['headers']['X-NC-NICKNAME'] = $nickName;
+		}
+
 		$options['body'] = \GuzzleHttp\Psr7\Utils::streamFor($content);
 
 		try {
@@ -38,6 +43,15 @@ public function droppingFileWith($path, $content) {
 			$this->response = $e->getResponse();
 		}
 	}
+		
+		
+	/**
+	 * @When Dropping file :path with :content as :nickName
+	 */
+	public function droppingFileWithAs($path, $content, $nickName) {
+		$this->droppingFileWith($path, $content, $nickName);
+	}
+
 
 	/**
 	 * @When Creating folder :folder in drop
@@ -52,7 +66,7 @@ public function creatingFolderInDrop($folder) {
 		}
 
 		$base = substr($this->baseUrl, 0, -4);
-		$fullUrl = $base . "/public.php/dav/files/$token/$folder";
+		$fullUrl = str_replace('//', '/', $base . "/public.php/dav/files/$token/$folder");
 
 		$options['headers'] = [
 			'X-REQUESTED-WITH' => 'XMLHttpRequest'
diff --git a/build/integration/filesdrop_features/filesdrop.feature b/build/integration/filesdrop_features/filesdrop.feature
index 211f780fb1c66..2c9156dea0268 100644
--- a/build/integration/filesdrop_features/filesdrop.feature
+++ b/build/integration/filesdrop_features/filesdrop.feature
@@ -59,3 +59,34 @@ Feature: FilesDrop
       | permissions | 4 |
     When Creating folder "folder" in drop
     Then the HTTP status code should be "405"
+
+  Scenario: Files request drop
+    Given user "user0" exists
+    And As an "user0"
+    And user "user0" created a folder "/drop"
+    And as "user0" creating a share with
+      | path | drop |
+      | shareType | 4 |
+      | permissions | 4 |
+      | attributes | [{"scope":"fileRequest","key":"enabled","value":true}] |
+      | shareWith |  |
+    When Dropping file "/folder/a.txt" with "abc" as "Alice"
+    And Downloading file "/drop/Alice/a.txt"
+    Then Downloaded content should be "abc"
+
+  Scenario: Put file same file multiple times via files drop
+    Given user "user0" exists
+    And As an "user0"
+    And user "user0" created a folder "/drop"
+    And as "user0" creating a share with
+      | path | drop |
+      | shareType | 4 |
+      | permissions | 4 |
+      | attributes | [{"scope":"fileRequest","key":"enabled","value":true}] |
+      | shareWith |  |
+    When Dropping file "/folder/a.txt" with "abc" as "Mallory"
+    And Dropping file "/folder/a.txt" with "def" as "Mallory"
+    And Downloading file "/drop/Mallory/a.txt"
+    Then Downloaded content should be "abc"
+    And Downloading file "/drop/Mallory/a (2).txt"
+    Then Downloaded content should be "def"