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If I delete a bunch of emails from outlook, can my manager still retrieve them and read them? If yes, can they view all the attachments?

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    Potentially. If the emails were there for any length of time they could easily have been caught in the backup cycle and therefore be retrievable. If you were "being monitored" then it would be possible to forward copies of your emails to someone else without you knowing. Have you been using your email for things you shouldn't? ;) – Mokubai May 25 '15 at 12:40
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    yes, I did something I regret. I'll be fired if my manager finds out, or worse... – Ben May 25 '15 at 14:02
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    @Mokubai Your comment should be a standalone answer. I think it's at least as relevant to the question as the outlook-specific features, and speaks to the greater point that anything that ever went across your employer's server should be considered possibly recoverable. – octern May 25 '15 at 15:32
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    I guess you know, but just to be sure: if you delete a sent message, it won't disappear from the recipient's mailbox. – Arjan May 25 '15 at 18:47
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    There's also a difference between "can my manager read my email", "can IT pass my email to my manager if asked", "will IT pass my email to my manager if asked", and "can and will IT pass my email to a court if my company is sued because of it". IT may not honour time consuming requests unless ordered to do so by someone quite high up in the company; they may have more important things to do. – gnasher729 May 26 '15 at 16:28
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If you're using Exchange Server then yes, this is easy, any deleted item(s) can be restored by authorized person including attachments within the retention period.

  • how long is the retention period? – Ben May 25 '15 at 13:08
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    It is configurable by the administrator. – thims May 25 '15 at 13:09
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    Depending on your Outlook version look for "Recover Deleted Items" and you can get an idea of how far back it goes. That portion is considered a feature in case people make mistakes. – Matt May 25 '15 at 14:54
  • In many database systems, deleted items are either merely flagged as deleted and ignored, or simply moved to a "deleted items" table. Many others store transactions (differences) which can be rolled back. Emails are/can be required to be stored long-term by law. – Yorik May 26 '15 at 18:00
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TL;DR: Can they? Almost certainly. Will they? Usually not, unless you give them reason to or they're a particularly bad workplace.

If the emails were there for any length of time they could easily have been caught in the backup cycle and therefore be retrievable in the event that anyone had a reason to suspect you had deleted something that might be important.

If you were being monitored then it would be possible for your IT department to forward copies of your emails to someone else without you knowing. It is also possible that your boss could have been given access to your email if you were under investigation for misconduct.

Because you used company property whatever you sent could have gone through any number of systems. Firewalls scanning for corporate secrets, virus scanners, and data protection systems could all have caught a copy or at the very least taken the subject line and a brief excerpt of the email.

Even if your company provides "free" WiFi as a courtesy this could easily be monitored and logged. Emails used to be sent in cleartext so anyone could read them if they wanted, thankfully encryption is more common in email clients now.

The thing here though is that in most countries giving this level of access would be considered unethical and potentially illegal unless some kind of disciplinary proceedings were under way. I would consider it "against the norm" for any workplace to attempt recovery or otherwise monitor employees without due reason. I have heard of places, but those places tend to have Banana Dictator Managers with little regard for the meat-sacks that litter their office and a high employee turnover as a result.

On the bright side, backups often get recycled or purged, logs get erased after a while and people forget.

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    And even if backups are not purged, they are rarely used for this purpose, unless there is a concrete suspicion. – GolezTrol May 25 '15 at 20:03
  • @GolezTrol Aye, I was trying to get to that point in my answer. Any reasonable workplace would trust their employees, let them have at least some leeway and privacy and not actively be doing this sort of thing without reason. They are completely able to do these sorts of things, but any ethical management system will not unless they suspect you of completely failing to do your job or have reasons to suspect you are abusing their property or systems. – Mokubai May 25 '15 at 20:36
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    "but those places tend to have Banana Dictator Managers" or happen to be in a heavily regulated industry, where sensitive information can be traded for illegal gains. – Aron May 26 '15 at 13:33
  • @Aron In that case I would argue that you would have clearly been told that "due to the nature of the work all communications are subject to active monitoring and inspection" and you would almost certainly not sent any emails of the type that OP appears worried about in the first place. You would already be aware that such monitoring is commonplace in your business and not need to ask if it is possible after the fact. I know of places where what you say is the case but assumed from context that this was a "more relaxed" workplace. – Mokubai May 26 '15 at 16:18
  • @Mokubai, What does "Banana" Dictator Managers mean? – Pacerier Nov 23 '15 at 19:42
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Unfortunately, anything you do on a employer laptop is considered property of the company. I'm sure you signed some sort of agreement when you started, indicating your laptop is the property of the company.

Even if you deleted the emails, your organization most likely will have a comprehensive backup strategy in place to recover anything deleted, even from several weeks back.

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    Hardware doesn't really factor into this question and ytour statement would be incorrect in several European countries where personal email for instance is protected against corporate oversight. – Lilienthal May 25 '15 at 21:25
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    I agree with your first paragraph, but your second paragraph doesn't ring true. I rarely ever see organisations with proper backup retention in place, and even when it is, getting back individual mailboxes or mailbox items are usually way too much work to bother with. Of course, it's not worth the risk to assume that they don't. – Mark Henderson May 25 '15 at 21:34
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There are multiple ways that email can be retained separate from a backup. The most common is called Journalling and it has nothing to do with Outlook. It merely duplicates all incoming messages and stores them in a secured place. This ensures that if the company is sued, etc., that it has a record of every email sent and received by the company.

In short, you should assume that every email you send or receive, every web page you visit, every porn file you download onto company property will be documented somewhere. As many of the others have stated these are rarely used unless there's a lawsuit or Intellectual Property at stake.

protected by Community Jul 17 '18 at 1:58

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