Based on the information provided in the extracts, it seems like you're dealing with a common issue where the access token expires before the sync operation is completed. This can happen if the access token has a short lifespan and the sync operation takes longer than this lifespan. In such cases, you need to ensure that your connector is set up to automatically refresh the access token when it expires. The

SingleUseRefreshTokenOauth2Authenticator

should handle this for you, but it's possible that there might be an issue with your implementation or the API you're connecting to. Here are a few things you can check: 1. Ensure that your connector is correctly using the

SingleUseRefreshTokenOauth2Authenticator

. This should automatically handle the refreshing of the access token. 2. Check the lifespan of your access token. If it's very short and your sync operations are long, you might need to find a way to extend the lifespan of the token or make your sync operations faster. 3. Check the logs for any errors or issues related to the token refresh process. This might give you more insight into what's going wrong. 4. If the API you're connecting to uses a refresh token that also expires, you might need to implement a custom solution to handle this. One user in a [forum discussion](https://discuss.airbyte.io/t/3275) mentioned a similar issue and ended up using a

SingleUseRefreshTokenOauth2Authenticator

. If you're still having issues, it might be helpful to provide more details about your implementation and the API you're connecting to. This could help identify any specific issues that might be causing your problem.

Not sure the sdk handles retries in that case. I can add a custom

should_retry

but that won’t recreate the authorization header (which would refresh the token)

I believe I’m

0.50.1

and Airbyte-sdk

0.40.5

@Sherif Nada any ideas on how to handle this edge case?

if everything goes well, the authenticator will never run into the case of the expired access token being used, instead it request a new one in time

Please double-check the expiration time coming from the token refresh endpoint is handled correctly by your connector

If it's actually

expired_in

in your case, you will need to adjust it

if that doesn't work, try logging debug information to see where things break down for your specific case

@Joe Reuter (Airbyte) I ended up adding a 10 minute buffer to the expiry time and that seemed to do the trick! Thanks for your help