Workflows in Waiting state may not be able to proceed if the owner of the workflow have been deactivated.
E.g. : The 'Work 365 Start Job' workflow waits for the scheduled date/time to perform its logic.
If the user who owns the workflow has been deactivated for any reason, the workflow will not run an expected and error out, with the workflow remaining in 'Waiting' state.
Work 365 always recommends to avoid using actual User accounts and instead use a Service Account for installing the Work 365 solution, which ensures that the Service Account is the owner of the workflows within the solution.
In instances where you face such an issue, please perform the below steps to re-run the errored workflow jobs.
#1
Change the owner of the workflow to the required Service Account
This step is required to ensure that the correct account is used for all the future workflow runs.
Navigate to Customizations - Processes and select the required Workflow (E.g.: Work 365 Start Job)
Open the workflow and use the Actions -> Assign menu to assign it to a valid Service Account.
If you are logged in with the Service Account, use the 'Assign to me' option and click 'Ok'
If you are logged in with any other account use the 'Assign to another user' option and select the required account and click 'Ok'. However in this case the workflow will be deactivated and you will need to reactivate it back again.
Navigate to Customizations - Processes and select the required Workflow (E.g.: Work 365 Start Job)
Open the workflow and use the Actions -> Assign menu to assign it to a valid Service Account.
If you are logged in with the Service Account, use the 'Assign to me' option and click 'Ok'
If you are logged in with any other account use the 'Assign to another user' option and select the required account and click 'Ok'. However in this case the workflow will be deactivated and you will need to reactivate it back again.

#2
Re-Run the existing workflow jobs which have errored out and are in 'Waiting' state.
The existing workflow jobs are still owned by the deactivated user and CRM does not provide the ability to change the owner of an existing workflow job. To ensure that these jobs can be re-run the deactivated user license needs to be activated from Office 365 Admin Centre.
Once activated, resume all the workflow jobs which have errored out in the 'Waiting' status.
For this, open the workflow and navigate to 'Process Sessions'.
Select all the required jobs which need to be re-run and click on 'More Actions' -> 'Resume'.

Select all the required jobs which need to be re-run and click on 'More Actions' -> 'Resume'.

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