There are a million reasons why people feel the need to sheepishly telegraph that they’ll be checking email while OOO: a toxic workplace culture; a set of bad managers who don’t model work/life balance or use manipulative tactics like saying, ‘feel free to take some time if you need it’; companies that are so focused on lean growth they don’t have anyone to pick up the slack when an employee opts to take time off. These days, merely having the confidence to step away from your job by taking the vacation time granted to you in the terms of your employment agreement is still a privilege in the American workforce.
I take advantage of the ability to send different OOO messages to internal or external addresses. Internal addresses get a couple of people to contact if it’s urgent, usually my direct report and my backup person, since between them they can cover pretty much everything I do, or at least they’ll know who can. External addresses get a more general notice: “I am temporarily out of the office. If your message is regarding the Llama Care project and requires a prompt response from our Llama Grooming Team, please make sure that [email protected] is one of the recipients of your message.” Probably not the most elegant phrasing, but we have a distribution list for this very reason. Even requests that they know only I handle are supposed to go to the LG list.

Like, relax. If the dates are outdated, you can probably safely assume I’ve returned already and that I’m spending my time getting back to people instead of worrying about my very clear out-of-office message. If you’re really concerned, you can contact the backup person whose information I provided IN THE MESSAGE to confirm or just, you know, text me.
If you’re traveling to a remote, mountainous area, why not jab some fun at your lack of WiFi in your autoresponder? Plus, that makes it less likely that people will expect an immediate response or continue to email you after the first try.