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I have SharePoint 2019 server setup on permise and setup Gmail as my SMTP. I then have setup a workflow for testing purpose that sends email when a task is created, pretty basic. When I create a task it wont actually send an email, I opened ULS Viewer and this is the error I got:

Context has no SMTP/UPN claims. IdentityContext: '{"nameid":"s-1-5-21-2587413344-3268338448-1829755020-1000","nii":"urn:office:idp:activedirectory","upn":"my.email@domain.com","userId":"0#.w|domain\\username","appliesTo":"https:\/\/sharepoint.domain.com\/"}'

I have the attribute mail fill in AD and email field.

Any ideas on where else to look ? thanks

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Not sure what happened although I think its one of the timer job but the issue fixed it self randomly. I tough I launched each timer job manually but maybe I was looking at the wrong one. Everything is working fine now.

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