diff --git a/apps/files_trashbin/lib/Trashbin.php b/apps/files_trashbin/lib/Trashbin.php
index bdd7323d4a2a5..eef6e9c2fd4ce 100644
--- a/apps/files_trashbin/lib/Trashbin.php
+++ b/apps/files_trashbin/lib/Trashbin.php
@@ -1211,12 +1211,13 @@ public static function getTrashFilename(string $filename, int $timestamp): strin
 		// oc_filecache `name` column has a limit of 250 chars
 		$maxLength = 250;
 		if ($length > $maxLength) {
-			$trashFilename = substr_replace(
-				$trashFilename,
-				'',
-				$maxLength / 2,
-				$length - $maxLength
-			);
+			// truncate at the middle, since the last characters are fairly likely to have meaningful information such as version numbering
+
+			$charsToRemove = $length - $maxLength + 1;
+			$charLength = mb_strlen($trashFilename);
+			$start = mb_substr($trashFilename, 0, floor(($charLength / 2) - $charsToRemove));
+			$end = mb_substr($trashFilename, floor($charLength / 2));
+			return $start . '_' . $end;
 		}
 		return $trashFilename;
 	}
diff --git a/apps/files_trashbin/tests/TrashbinTest.php b/apps/files_trashbin/tests/TrashbinTest.php
index b6bb552517773..b2233bc2509ac 100644
--- a/apps/files_trashbin/tests/TrashbinTest.php
+++ b/apps/files_trashbin/tests/TrashbinTest.php
@@ -32,6 +32,7 @@
 use OCP\IUserManager;
 use OCP\Server;
 use OCP\Share\IShare;
+use PHPUnit\Framework\Attributes\DataProvider;
 
 /**
  * Class Test_Encryption
@@ -706,6 +707,33 @@ public static function loginHelper($user, $create = false) {
 		\OC_Util::setupFS($user);
 		Server::get(IRootFolder::class)->getUserFolder($user);
 	}
+
+	public static function trashFilenameProvider(): array {
+		return [
+			['foo.txt', 'foo.txt.d1234'],
+			[
+				'a_very_long_filename_with_a_lot_a_characters_such_that_it_reaches_the_file_length_limit_and_would_cause_issues_if_we_just_appended_the_' .
+				'timestamp_because_then_the_combined_length_would_overflow_the_column_limit_of_the_filecache_and_truncate_in_db.txt',
+				'a_very_long_filename_with_a_lot_a_characters_such_that_it_reaches_the_file_length_limit_and_would_cause_issues_if_we_just_ded_the_' .
+				'timestamp_because_then_the_combined_length_would_overflow_the_column_limit_of_the_filecache_and_truncate_in_db.txt.d1234'
+			],
+			[
+				'a_very_long_filename_with_a_lot_a_characters_such_that_it_reaches_the_file_length_limit_and_would_cause_issues_if_we_just_äøšá_the_' .
+				'timestamp_because_then_the_combined_length_would_overflow_the_column_limit_of_the_filecache_and_truncate_in_db.txt',
+				'a_very_long_filename_with_a_lot_a_characters_such_that_it_reaches_the_file_length_limit_and_would_cause_issues_if_we_ju_á_the_' .
+				'timestamp_because_then_the_combined_length_would_overflow_the_column_limit_of_the_filecache_and_truncate_in_db.txt.d1234'
+			],
+		];
+	}
+
+
+	#[DataProvider(methodName: 'trashFilenameProvider')]
+	public function testGetTrashFilename(string $filename, string $expected): void {
+		$result = Trashbin::getTrashFilename($filename, 1234);
+		$this->assertTrue(mb_check_encoding($result, 'UTF-8'));
+		$this->assertEquals($expected, $result);
+		$this->assertTrue(strlen($result) <= 250);
+	}
 }
 
 // just a dummy class to make protected methods available for testing