diff --git a/lib/private/Files/Storage/Wrapper/Quota.php b/lib/private/Files/Storage/Wrapper/Quota.php
index b0ff0117b960f..a7fd91b1f4c6a 100644
--- a/lib/private/Files/Storage/Wrapper/Quota.php
+++ b/lib/private/Files/Storage/Wrapper/Quota.php
@@ -230,7 +230,7 @@ public function writeStream(string $path, $stream, ?int $size = null): int {
 		}
 
 		if ($size !== null) {
-			if ($size < $free) {
+			if ($free < 0 || $size < $free) {
 				return parent::writeStream($path, $stream, $size);
 			} else {
 				throw new NotEnoughSpaceException();
diff --git a/tests/lib/Files/Storage/Wrapper/QuotaTest.php b/tests/lib/Files/Storage/Wrapper/QuotaTest.php
index 150917b9dd9e9..9c317d6d815fc 100644
--- a/tests/lib/Files/Storage/Wrapper/QuotaTest.php
+++ b/tests/lib/Files/Storage/Wrapper/QuotaTest.php
@@ -251,6 +251,26 @@ public function testNoWriteStreamQuota(): void {
 		$instance->writeStream('files/test.txt', $stream);
 	}
 
+	public function testWriteStreamAllowsUploadPathWithUnlimitedFreeSpace(): void {
+		$storage = $this->getMockBuilder(Local::class)
+			->onlyMethods(['free_space'])
+			->setConstructorArgs([['datadir' => $this->tmpDir]])
+			->getMock();
+		$storage->expects($this->any())
+			->method('free_space')
+			->willReturn(Files\FileInfo::SPACE_UNLIMITED);
+		$storage->mkdir('uploads');
+
+		$instance = new Quota(['storage' => $storage, 'quota' => 5.0]);
+
+		$stream = fopen('php://temp', 'w+');
+		fwrite($stream, 'foobar');
+		rewind($stream);
+
+		$this->assertEquals(6, $instance->writeStream('uploads/chunk', $stream, 6));
+		$this->assertEquals('foobar', $instance->file_get_contents('uploads/chunk'));
+	}
+
 	public function testNoWriteStreamQuotaZero(): void {
 		$instance = $this->getLimitedStorage(0.0);
 		$stream = fopen('php://temp', 'w+');