diff --git a/app/src/main/java/eu/faircode/email/ServiceAuthenticator.java b/app/src/main/java/eu/faircode/email/ServiceAuthenticator.java
index 268c38f127..a194dd7b8f 100644
--- a/app/src/main/java/eu/faircode/email/ServiceAuthenticator.java
+++ b/app/src/main/java/eu/faircode/email/ServiceAuthenticator.java
@@ -151,6 +151,8 @@ public class ServiceAuthenticator extends Authenticator {
             long now = new Date().getTime();
             Long expiration = authState.getAccessTokenExpirationTime();
             boolean needsRefresh = (expiration != null && expiration < now);
+            if (needsRefresh)
+                authState.setNeedsTokenRefresh(true);
 
             if (!needsRefresh && forceRefresh &&
                     expiration != null &&
diff --git a/app/src/main/java/eu/faircode/email/ServiceSynchronize.java b/app/src/main/java/eu/faircode/email/ServiceSynchronize.java
index e127576aed..2248b69b6a 100644
--- a/app/src/main/java/eu/faircode/email/ServiceSynchronize.java
+++ b/app/src/main/java/eu/faircode/email/ServiceSynchronize.java
@@ -64,6 +64,8 @@ import com.sun.mail.imap.IMAPStore;
 import com.sun.mail.imap.protocol.IMAPProtocol;
 import com.sun.mail.imap.protocol.IMAPResponse;
 
+import net.openid.appauth.AuthState;
+
 import org.json.JSONObject;
 
 import java.io.File;
@@ -2356,7 +2358,10 @@ public class ServiceSynchronize extends ServiceBase implements SharedPreferences
 
                             if (!account.isTransient(this)) {
                                 Long expirationTime = iservice.getAccessTokenExpirationTime();
-                                if (expirationTime != null && expirationTime < trigger) {
+                                if (expirationTime != null &&
+                                        expirationTime < trigger &&
+                                        expirationTime > new Date().getTime()) {
+                                    expirationTime += AuthState.EXPIRY_TIME_TOLERANCE_MS;
                                     EntityLog.log(this, EntityLog.Type.Debug, "Expedite keep alive" +
                                             " from " + new Date(trigger) + " to " + new Date(expirationTime));
                                     trigger = expirationTime;