Out of Office Assistant not replying

I’ve enabled my Out of Office Assistant (OOF) and have sent myself a message from my private account to see how it would arrive. Sadly, I never received this automatic reply.

Why isn’t it working and how can I make it work reliably?

Automatic Replies buttonWhen it comes to setting the Out of Office Assistant (OOF) there are 3 things to note;

  1. By default, it doesn’t reply to people outside of your organization.
  2. It only replies once per address.
  3. It could get filtered out by Junk Email Filters.

In addition, note that it is an Exchange account feature. To get similar functionality for POP3, IMAP and Outlook Connector accounts see this guide instead.

OOF doesn’t reply outside of the organization

By default, Exchange is configured not to send out Out of Office messages to addresses that are not within your company’s Exchange environment.

If you send yourself a message by using your Exchange account instead of your external private account (or ask your colleague to send you a test message), you should receive an Out of Office message.

If it works now, you can ask your Exchange administrator to turn on the Automatic Replies feature on the Exchange server or to verify if it has been configured properly. A guide for this can be found here;
Allow Automatic Forwarding/Replying to the Internet

Automatic Replies - OOF - Outside My Organization - My Contacts only
When Automatic Replies to the Internet is allowed on Exchange, you can set it to reply to your contacts only to prevent replying to spam messages and unknown people.

OOF only replies once per address

Once you’ve configured the OOF, it will only reply once per address. To have it send the OOF message to all addresses again, you must turn off the OOF and then turn it back on.

If you want to reply to each message that you receive, no matter how often that person has emailed you, you can emulate the OOF function by a server-side rule similar as described here; Out of Office exceptions

Note: For client-side rules, automatic replies initiated by a rule will only reply once per address per Outlook session and Outlook needs to be running in order to process it.

OOF messages can be filtered out by Junk Email Filters

As OOF messages are automated messages, they have a higher likelihood to get filtered out by Junk Email Filters. Especially various free providers tend to filter them out. If you are using a POP3 account, log on to your web based mailbox and see if it got delivered to the Junk E-mail folder there.

While you might be able to fix this for your own mailbox with your provider, there is nothing you can do to make sure it doesn’t happen for other receivers.

If you need to be a 100% certain that they get informed about your (extended) absence, contact them before you leave. Then if they would then send you a message and receive your OOF, it would be more like a friendly reminder. You’ll probably receive less mail during your absence then as well and thus less to deal with when you return.

To pro-actively inform multiple people that you are away, you could use a Mail Merge.

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