Automations can factor in return dates.
This example shows the following rule: If a user is still out of the office for more than one day at the time of issue assignment, the issue can be reassigned to a specific user or to a user in a group. The new assignee will be notified of the reason via a comment on the issue.

Configuration of the rule

Create the rule

The rule itself is based on the example Basic - Unassign an out-of-office user. So after checking the users out-of-office status the following steps can be added.

Create a variable “oooEndDate” to store the “endDateTime” from the data object.

Check if the “oooEndDate” is empty OR the date difference is bigger than 1

Temporarily store the current assignee display name in a variable “oooassignee“

Assign a specific user or a user from a group

Re-fetch the data of the issue

This step is needed to get the new assignee from the previous step

Add a comment to inform the new assignee