If you currently have Modern Authentication enabled in your GP 18.4 environment (which if you're using Exchange email, you most likely do) it's normal that when a user logs into Dynamics GP and then submits or attempts to approve/reject a workflow pending their approval, they'll be prompted for their Exchange credentials via the 'Sign in to your account' windows you mention, as that is what Workflow will send the emails through.
The SMTP account/server is only used, when Modern Auth is enabled, to send out test emails, otherwise it isn't used at all. The exception would be when approving workflows through the email notification links, which is using Web Services functionality. Since Web Services doesn't use Modern Auth at this point, it defaults to emailing through the SMTP server/account specified in the Workflow Setup window.
This process of asking for the Exchange credentials is also true when emailing something non-workflow related or accessing a email window.
It should ask for the user's Exchange credentials and use those to email through, for as long as the user is logged into Dynamics GP.
It seems the issue you're seeing is "email notifications for that submission will not be received but a new one will work after that. This can go for an hour without issue and then pop up during a submission or a save to changes in the workflow"....
What email is not being received? Is it the email to the approver(s) letting them know a workflow is assigned to them and pending their approval, or is it the emails sent to the originator/submitter letting them know when a workflow is submitted, approved, final approved, etc., if applicable based on your setup?
I ask because with 18.4, on different builds we had different issues with the workflow emails, more so the emails to the originator/submitter than the approvers, and these issues were pretty much resolved in the latest 18.5 releases.
Also, if emails are working and then not working, I'd be curious if you see the emails making it into the SENT folder of the Exchange account of the submitter or approver, depending on which account the email is coming from, to see if it's being generated by Dynamics GP but not sent to the recipient, or not being generated.
It also doesn't hurt to run this script against the GP system database:
EXEC wfDeployClrAssemblies
Thanks,
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