former boss is monitoring my old email account

A reader writes:

I have an old boss who completely screwed me over (I should have seen the signs, but I trusted him as a friend and colleague, stupid me). A year later, I’m better off for it, but I will never forgive or forget.

Anyway, it’s now been more than a year since my departure, and a friend accidentally sent an email to my old work address. He wrote my friend back that it was sent in error. Not to all my friends who were on the thread, just to the one he knows is my best friend and who he has met before. And he made a snippy comment to her — that if I was her friend, shouldn’t her records be updated?  

I feel he does this expressly to keep his one psychopathic foot in my personal life, because as at this point, personal emails are the only thing that could be filtering into that inbox, by mistake. His sham company is out of business anyway. And his writing back my friends I feel is stepping over the line.

A year later, it is normal practice to:
a) Monitor the emails of a company that no longer exists – maybe
b) Respond to my friends – not business contacts in anyway and never will be
c) Respond snidely

Yes, it’s normal to continue to monitor emails. But he sounds like a jerk. Which you already knew, so there’s not really new information for you here. I’d put it out of your mind.

As we discussed recently, employers often continue to receive email at the accounts of employees who are no longer with the company, so that they can see and deal with anything work-related that comes in there. The company owns that email account; if you choose to use it for personal things, be aware that this is a potential consequence. So that part is normal.

And frankly, writing back to your friend to let her know that her email hadn’t reached you would have been a courteous thing to do — if he hadn’t included the snide comment. (And he might have only responded to her rather than the whole group cc’d because she was the one who sent the email.)

But yes, the comment he decided to add was snide and obnoxious. He does indeed sound like an ass.

But whether or not it was an attempt to keep one psychopathic foot in your personal life,” or just general obnoxiousness, who cares? You already knew he was a jerk, you don’t work for him anymore, and he has no power over you … unless you give him that power by allowing him to take up space in your mind.

Laugh at what a twit he is, and move on.

Read an update to this letter here.

{ 33 comments… read them below }

  1. Rob*

    That last full paragraph is key. Don’t let him maintain his power over you. By doing so, he ‘wins’ whether he realizes it or not.

    Use this negative experience to fuel you in a positive manner not only in your current work situation, but all future work situations you find yourself in. It will make you a better person, and you will be much better off as a result.

  2. Another Emily*

    This is great advice. I totally get that it’s annoying to have a loose end that you can’t tie up, but there’s no use worrying about something you can’t control.

    If his company went bust then maybe he’ll eventually stop bothering to pay for the domain and the email account will die. Put it out of your mind, this jerk isn’t worth wasting head space on.

  3. Wilton Businessman*

    I always have my former employees email forwarded to me. I check it once a month for any new non-spam messages. If it’s something addressed directly to that person, I respond that XYZ doesn’t work in the Chocolate Teacup department any more. Found out that one of my former employees was doing a side business with his work email (which is specifically prohibited from company rules).

    1. JT*

      After a few months, I’d suggest setting up an auto-reply saying the person is know longer with the company, and including contact info for the appropriate person.

  4. Anonymous*

    I understand AAM’s answer, but the OP did mention her former employer is out of business. Does everything still play out with the same answer?

    To the OP, maybe just re-email your friends to remind them to delete that old email address as you are not with that company anymore and give them the email address they should contact you with. No need to explain anything other than saying maybe they won’t get a response from you if they send it to that old one.

    1. Ask a Manager* Post author

      I think so, even though the business is closed. If I had a business that had closed, I’d still want to make sure that contacts who reached out to me or an employee were getting a response (which would probably just be “hey, we’re not open anymore”) rather than thinking my business was ignoring them. And you could use an auto-reply for that, but there might be some people who you had a reason for wanting to talk to personally.

  5. Kimberlee*

    I actually get email, straight to my inbox, from the last 4 or 5 people in my position. It’s a high turnover position and, honestly, I’m really glad for it. There are TONS of accounts all over the place with people years backs’ names on them. I would never know about them otherwise!

    But in a company that no longer exists… yeah. I agree with AAM that they ideal is that he sends a polite form letter that you no longer work there. But it is a little weird that he’s still monitoring email for so long, unless the company went defunct less than 6 month in the past (and once you shut down and the email is no longer valid, it would bounce back to the owner, serving the same purpose as a polite “he’s no longer working here” response email.

  6. mh_76*

    Could he have set up an auto-reply instead? “Wile E. Coyote no longer works for Acme Corporation. If your email is business-related, it will be routed and addressed accordingly. If your email is personal in nature, please update your address book with Mr. Coyote’s personal email address [not given out in the auto-reply…or ever by the boss]. Sincerely, John D. Roadrunner [maybe doesn’t even need a name on this one…debatable].” … or something to that effect. Not quite perfect but would save the boss from feeling like he to reply (but wouldn’t save him from checking for biz-related emails). That snide remark was uncalled for.

  7. Ellen M.*

    What if the former boss was replying to messages AS the former employee. That could cause a problem, no?

  8. JessB*

    I left a horrible workplace in a hurry a few years ago, and for a while, I was haunted by the fact that I never got to clear out my email account, or delete my internet browsing history to get rid of saved passwords. I updated email addresses for the newsletters I was getting to my work address (which were work related, and as they related to my field I wanted to continue getting them) and changed all my passwords, but I really thought about it a lot.

    Then, I got a new job, and did a lot of fun stuff, and just forgot about the old place. Every now and then I’ll remember them, but I think Alison’s advice to stop allowing your crazy ex-boss space in your mind is spot on. It’s difficult to get past it, but you can do it, and it’s so great when you do.

    1. Piper*

      Definitely seconding your second paragraph. A little over a year ago I had an awful experience with a boss/company owner who had been my friend previously. After that ended, I ended up in an equally awful (but different) situation and I was so bitter because it was my former boss/friend’s fault I got stuck in that situation. But now, I finally landed a really good gig at a high profile company, and it’s become so much easier to put that insanity behind me.

      It’s hard when you still feel like the former boss is “winning” because you’re still in a crappy situation, but once you’re out of it, it becomes easier to let it all go.

  9. John Hunter*

    It seems perfectly sensible for a boss to monitor an email account for a former employee. The snide comment is uncalled for but as you mention the notice to someone that the person is no longer there is helpful.

    I think people often fail to realize a business email account is really for the business. It is fine to use it for person stuff (I think) but unwise to not think of the consequences (you leaving the company, saying really foolish things “on the record” even if semi-privately [email] – I believe the business has the right to look at your email…).

    1. Tamara*

      This sums it up pretty well. Any time you use a business account, if you don’t consider that the company owns it, you’re setting yourself up for problems. Personally, I won’t do it at all, but I know many people who do. Although I can’t think of anything I’ve sent from my personal email that would cause problems at work, it’s so easy to set up a free personal account – it just doesn’t seem worth the potential headache.

      1. Anonymous*

        This is so true! Gmail, Hotmail, Yahoo! and a zillion other places can provide you with a free web-based email account that goes with you anywhere. You never know when you might unexpectedly get laid off. Don’t tie up your personal email with your work email address.

        1. mh_76*

          and if some of your colleagues/co-workers become friends and personal emails start crossing your work inbox, reply to them that you’re using your home email for personal emails and include your home email address -and- set that message’s reply-to address to your home email. Also cc your home email addr. on the reply. They’ll get the message quickly: work stuff to work email, personal stuff to home email. Also, if you know about your departure from a job in advance, it’s ok to send out a see-you-later email to people who you’d like to keep in touch with and include your personal email address…but don’t forget to say that all work-related correspondence should go to x person who’s still at your soon-to-be-old company.

  10. Eva*

    I had a similar problem a while back. I resigned from a toxic workplace and agreed with the management that my email would continue running for 3 months with an auto-reply that the email is no longer in use but with forwards to both myself and the person who replaced me for follow-up etc. It was to be deactivated after the 3 months and after 3 months i was advised that this had been done.
    A little background. I am in HR and receive a lot of confidential information from staff in the branches, business partners, managers etc. Hence the very specific arrangement that was made about my email account.
    You can imagine my horror when a year later, the IT person forwarded an email to me that had been received in my old account that they wanted me to respond to. To be specific, it was a confidential email from another company on a matter that i had been handling while employed there and the IT guy ‘ didn’t know who to forward it to’!
    I raised a ruckus and communicated with the management of this company about the still active email address and the possible leak of confidential information. They wrote back to me and told me they would handle it but as i said previously, it was a toxic work environment. I don’t believe they have done anything about it to date because i received another email from IT ‘recommending’ that i help a member of staff for whom another company had sent a reference request. Oh, there was a snide comment in there too about trying to get IT guy in trouble but not succeeding.

    1. Josh S*

      It could very easily be that the email has been disabled, but that they have undeliverable emails going to a default address.

      Let’s say the company is CompanyABC, and their email addresses all end in . Any email that gets sent to a valid address (say, your old boss, Joe(at) gets routed to that person’s inbox, like you’d expect it to. But any email that is addressed to an INVALID email (say, if someone tried to email Jeo(at) gets routed to a default/catchall email address, which is usually something like webmaster(at) And it’s usually an IT guy who ends up getting that email and deciding what to do with it–delete it, handle it himself, or forward it on to the correct party.

      In your case, they kept the Eva(at) email alive for 3 months, and then killed it. But even after that point, whenever an email gets sent to Eva(at), it bounces to the default inbox–webmaster(at) The IT guy has no idea about your agreement with management, and doesn’t really care about the confidentiality stuff–he just wants to make sure it gets dealt with properly.

      So he reaches out to you (which is pretty inappropriate, since you’ve been gone from the company for a while now) and says, “What should we do to handle this!?”

      You may want to reach out to the company–probably the IT guy that’s calling you, rather than someone in management who may not understand the technical bits of what’s going on–and ask them to either A) delete any messages sent to Eva(at) or B) send an auto-response saying that Eva is no longer with the company, emails sent to this address are likely to not be confidential, and that future communication should be sent to NewHRPerson(at) .

      It really may not be that they’re trying to be evil here. It’s probably just the technical implications that management doesn’t realize is happening because they don’t grok IT stuff.

      1. Jamie*

        “It could very easily be that the email has been disabled, but that they have undeliverable emails going to a default address.”

        This was my first thought. If you send an email to JoshS @Jamie’ I’ll get it (albeit quarantined) – even though he doesn’t and has never worked here. (Although with his ability to explain the technical bits and grok IT stuff (love that), I wish he did.)

        1. Josh S*

          That’s one thing I’ve learned is a strength of mine–I’m good at explaining things in terms that are understandable to those who aren’t expert in a given field. I’ve considered being a “Business Analyst” for software developers–I’ve seen so many of them who either can’t translate the requirements from the end user to the technical needs, or who can’t explain the technical implementation into layman’s terms for the users. So frustrating!

  11. Katrina Prock*

    Just laugh at the fact he’s so bitter and negative that he still has to be snide a year later. Then be thankful you don’t go home to him every night.

  12. Long Time Admin*

    The first thing that came into my mind was: get over yourself, girl.

    That sounded pretty judgmental to me, so I re-read the post to make sure I was “getting” it.

    Yes, the boss is a jerk.

    Yes, he owns the email, and he has every right to read it.

    Yes, the OP is over-reacting to this.

    It doesn’t sound like he’s stalking her or anything like that, so my first thought is maybe 50% correct. People actually think about us less than we think they do.

    The reason you should not automatically “forgive & forget” is that you now know that people do these things, and you can watch out for the behavioral red flags when they appear in the future.

    My suggstion is to let it go, and don’t use your business email for personal emails.

  13. Anonymous*

    Since this business is closed, he probably has a catch-all address, so that he’s receiving any email that comes to that domain, rather than monitoring individual email addresses.

  14. Ry*

    Bleah, I would be annoyed by this too. So glad you’ve moved on! OP, your best friend must be aware of how strange Former Boss was, right? So hopefully no harm done, although it was unprofessional of him to write snidely about you.

    I know it’s unnecessary drama, but.. but… give us some background, please? Why did you have to leave? Why did the business close? How come Former Boss is still monitoring your former email account from his defunct business? Why doesn’t he have better things to do?

    I’m currently planning to leave my job, which my employer knows. I have TONS of sensitive, work-related information in my work email account. I’m in the process of:

    1. Scouring the account for anything that isn’t necessary for business, or anything protected by HIPAA (basically, information about specific patients that nobody needs but me)

    2. Creating a .pst of everything n0n-HIPAA-violating that may be necessary for others to read

    3. Setting my out-of-office to read that I’m gone and emails should be directed to Ms. Replacement

    Anything else I should be doing, while we’re on the subject?

    1. Ask a Manager* Post author

      Sort your Sent folder by name, and then delete anything sent to yourself, friends, or family. When dealing with former employees’ email, that’s where I usually found the personal stuff I didn’t want to see.

      1. Jamie*

        Especially important if any emails to co-workers who will still be working there could be misconstrued.

        You don’t want someone grilled about an off-hand private joke shot off in email.

  15. Anonymous*

    Just a note…I assume you’re in the US, but in other countries this is illegal. I used to own a company in Argentina, and the legal protocol is to delete the account, and to create an automatic response to that old account saying that the employee no longer works at the company, and that all emails for her area should be sent to [new address]. That way, any issues are attended to, and the company cannot see any emails that were specifically directed to her, personal or otherwise. It just involves an extra step for the sender to re-send the initial email to the new address.

    Just thought I’d throw that in there for international readers…check your country’s legal requirements.

  16. Kate*

    When employees leave our company for whatever reason, we forward emails they receive — either to the new person in their old role, or to their supervisor. This is simply good business practice; even with the departure of the individual, work goes on, and we don’t want to potentially-important communications to be misdirected.

    Simply deleting the email account has the potential to confuse a customer. Would you simply just delete or inactivate someone’s phone/voice mail extension, so that someone who calls an absent employee (or vacationing/out-sick employee) gets a bizarre beep with no message? No, you’d re-route it automatically to someone else in Sales, or Billing, or whatever.

    Employees might be weirded out that personal emails might be forwarded to a coworker after they leave, but why were they receiving and sending personal emails on the company’s account to begin with? Besides, we simply don’t have time to create individual sorting protocols for everyone’s accounts. At the end of the day, only a person, not an Outlook algorithm, can decide whether an email to a business address was important or not, personal or not.

  17. Jungle Jane*

    I guess it might depend on the kind of job you had with the company but NO it is not normal practice to monitor a former employees company email for an entire year.

  18. Fred*

    I am in IT — yes, it is perfectly normal for businesses to monitor e-mail of former employees for extended periods of time. How long depends on what you did AND why you left. If you left under bad circumstances (which, reading between the lines you did), and if your job put you in a position to hurt the company, your boss may be looking for any evidence that you are acting inappropriately.

    Even when you are an employee, your company e-mail is not private. IT, legal, your boss, coworkers — all may have legitimate reasons to get into your e-mail and so may run across whatever is in there.

    Lesson learned for you — keep your business life and personal life separate. The company owns your e-mail. They did not provide it for you to carry on personal conversations.

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