diff --git a/apps/federation/lib/BackgroundJob/GetSharedSecret.php b/apps/federation/lib/BackgroundJob/GetSharedSecret.php
index b4ad46febc2bf..dcd1f85707c82 100644
--- a/apps/federation/lib/BackgroundJob/GetSharedSecret.php
+++ b/apps/federation/lib/BackgroundJob/GetSharedSecret.php
@@ -112,6 +112,7 @@ protected function run($argument) {
 		// kill job after 30 days of trying
 		$deadline = $currentTime - $this->maxLifespan;
 		if ($created < $deadline) {
+			$this->logger->warning("The job to get the shared secret job is too old and gets stopped now without retention. Setting server status of '{$target}' to failure.");
 			$this->retainJob = false;
 			$this->trustedServers->setServerStatus($target, TrustedServers::STATUS_FAILURE);
 			return;
diff --git a/apps/federation/lib/BackgroundJob/RequestSharedSecret.php b/apps/federation/lib/BackgroundJob/RequestSharedSecret.php
index f8c25168b56ce..e89e5ff79e4d6 100644
--- a/apps/federation/lib/BackgroundJob/RequestSharedSecret.php
+++ b/apps/federation/lib/BackgroundJob/RequestSharedSecret.php
@@ -116,6 +116,7 @@ protected function run($argument) {
 		// kill job after 30 days of trying
 		$deadline = $currentTime - $this->maxLifespan;
 		if ($created < $deadline) {
+			$this->logger->warning("The job to request the shared secret job is too old and gets stopped now without retention. Setting server status of '{$target}' to failure.");
 			$this->retainJob = false;
 			$this->trustedServers->setServerStatus($target, TrustedServers::STATUS_FAILURE);
 			return;
diff --git a/apps/federation/lib/SyncFederationAddressBooks.php b/apps/federation/lib/SyncFederationAddressBooks.php
index 2c59824113142..56256e06dc43a 100644
--- a/apps/federation/lib/SyncFederationAddressBooks.php
+++ b/apps/federation/lib/SyncFederationAddressBooks.php
@@ -78,6 +78,10 @@ public function syncThemAll(\Closure $callback) {
 					$this->dbHandler->setServerStatus($url, TrustedServers::STATUS_OK, $newToken);
 				} else {
 					$this->logger->debug("Sync Token for $url unchanged from previous sync");
+					// The server status might have been changed to a failure status in previous runs.
+					if ($this->dbHandler->getServerStatus($url) !== TrustedServers::STATUS_OK) {
+						$this->dbHandler->setServerStatus($url, TrustedServers::STATUS_OK);
+					}
 				}
 			} catch (\Exception $ex) {
 				if ($ex->getCode() === Http::STATUS_UNAUTHORIZED) {
diff --git a/apps/federation/tests/SyncFederationAddressbooksTest.php b/apps/federation/tests/SyncFederationAddressbooksTest.php
index 782ca52322abe..15ad2ee035946 100644
--- a/apps/federation/tests/SyncFederationAddressbooksTest.php
+++ b/apps/federation/tests/SyncFederationAddressbooksTest.php
@@ -111,4 +111,35 @@ public function testException() {
 		});
 		$this->assertEquals(2, count($this->callBacks));
 	}
+
+	public function testSuccessfulSyncWithoutChangesAfterFailure() {
+		/** @var DbHandler | MockObject $dbHandler */
+		$dbHandler = $this->getMockBuilder('OCA\Federation\DbHandler')
+			->disableOriginalConstructor()
+			->getMock();
+		$dbHandler->method('getAllServer')
+			->willReturn([
+				[
+					'url' => 'https://cloud.drop.box',
+					'url_hash' => 'sha1',
+					'shared_secret' => 'ilovenextcloud',
+					'sync_token' => '0'
+				]
+			]);
+		$dbHandler->method('getServerStatus')->willReturn(\OCA\Federation\TrustedServers::STATUS_FAILURE);
+		$dbHandler->expects($this->once())->method('setServerStatus')->
+			with('https://cloud.drop.box', 1);
+		$syncService = $this->getMockBuilder('OCA\DAV\CardDAV\SyncService')
+			->disableOriginalConstructor()
+			->getMock();
+		$syncService->expects($this->once())->method('syncRemoteAddressBook')
+			->willReturn('0');
+
+		/** @var \OCA\DAV\CardDAV\SyncService $syncService */
+		$s = new SyncFederationAddressBooks($dbHandler, $syncService, $this->discoveryService, $this->logger);
+		$s->syncThemAll(function ($url, $ex) {
+			$this->callBacks[] = [$url, $ex];
+		});
+		$this->assertEquals('1', count($this->callBacks));
+	}
 }