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We are aware of an issue where the Gmail® and Microsoft 365® (Outlook) integrations may stop working after TaxCycle has been left open for more than an hour. While sending an email immediately after connecting may succeed, subsequent emails may fail to send until the connection is refreshed.
If you encounter this issue, and have recently connected to either integration by following the steps in the help topic, please try these steps in order:

For instructions on managing your connections, including how to disconnect and reconnect, refer to the Gmail® Integration and Microsoft 365® (Outlook) Integration help topics.
We will resolve this issue in the next TaxCycle update.