How should IT handle repeated out-of-office requests for employees?

For organizations that genuinely need managers or HR to do this, automation can work. A controlled form or service portal can trigger a workflow, verify that the requester is authorized to act for the employee, and set the mailbox's scheduled automatic replies without giving broad administrator access. That should be an intentional service with clear ownership, not something that quietly lands in the general help desk queue.

If they want a supported process for managers, give them a form instead of allowing informal tickets. Require the employee, start and end times including the time zone, approved internal and external wording, a cover contact, and an authorized requester. Keep automatic replies separate from mailbox delegation or forwarding, since those need their own approvals.

Make this a policy decision rather than an ad hoc IT task. For planned leave, close the ticket with instructions for setting or scheduling automatic replies in Outlook on the web or mobile. Forgetfulness is not an IT incident, and repeatedly doing it for people just reinforces the behavior.

Our rule is that IT does not change a user's mailbox settings unless there is a specific business or emergency need, such as an employee leaving the organization. If the client insists that IT provide this as an exception service, charge the normal minimum billable amount and show the client how much the requests have cost over time.

A short one-page guide or internal knowledge-base article is probably the best first step. Explain that employees can schedule automatic replies in advance, and include the mobile and web instructions. You can also track requests by department and use the numbers to demonstrate that the current process is a policy and training problem, not a technical one.