I've spent a lot of time performing mail migrations for companies that either had very little IT focus, or no fulltime staff to handle common issues. As a result, policies governing email use and best-processes were never instituted. The end-users in these environments are non-technical and tend to resist change.

I definitely understand the mechanics of changing/moving/upgrading mail platforms. In most cases, I assist firms in moving from Linux-based POP3 or IMAP to Microsoft Exchange. This type of move exposes a multitude of user bad habits.

My concern isn't entirely about the disk space involved in the email hoarding issues I've encountered in the past; there's always one in every company. It's about the issues and abuses that I commonly see once I'm working with a particular firm.

During the last migration, I saw:

  • Users who CC: themselves on every email (presumably as a way to keep track of message threads?).

  • 300 Megabyte messages in the Sent Items folder?!?

  • People who send Outlook read receipts on every outgoing message.

  • Users who maintain subfolders for every contact that they correspond with. Sometimes manually. Sometimes with very broken client-side rules.

  • Over-organization of subfolders. (some folders with only one message in them).

  • Subfolders under the Inbox (I'm not sure if this is a bad practice, but it feels wrong).

  • Gratuitous use of Priority Flags. Everything is High Importance!!

  • 4+ years of email in the Sent Items folder.

  • 25,000 or more items in the Inbox (with a large percentage of them unread).

  • 15,000 or greater messages in the Deleted Items folder.

  • A user with 24,000 items in their Drafts folder! (the result of a misapplied client-side rule).

  • Auto-archives growing out of control.

How does this happen?

  • Is it that email is relatively new, and users aren't educated on how to utilize it well?
  • Is it a UI problem where the Deleted Items folder is simply a one-key filing system?
  • Are administrators not doing their part to gently help correct actions?
  • If the users have problems with basic email, how do I tackle the challenge of teaching them about out-of-office replies and how to work the group calendar (gulp)?

My question is whether there's a standard set of guidelines on how to manage one's email? (even a pamphlet?)

The user education issues tend to slow down these deployments because I'm altering the workflow that people have arrived upon through a variety of means. And when this affects people at all levels/roles of an organization, it seems like there's no standard in place.


Situations like these are the result of a couple of factors:

  • No formalized education on mail usage
  • Folk-wisdom based transmission of common tasks like vacation rules and how to set up automatic filers
  • Lack of pain for not deleting anything

These days, we're not quite at the point where a majority of the overall workforce has been dealing with email their entire careers but it's getting there. But we're definitely past the 50% mark for people who've been dealing with it for over a decade now, so there is a lot of bad-past-practice still in there.

The last Exchange environment I was involved with had all of those problems. Some of it was due to a certain minority who insisted in non-Outlook interfaces to Exchange which had.... side-effects. Some of it was the result of random flailing until it looked about right, then left alone for five years.

Email management is an intensely personal thing, and being forced from on high by The Man to file things just so because some silly pamphlet said that's the way it should be is not met warmly. In environments with extremely tiny mailbox quotas you end up with PST-files-of-unusual-size that look just like your too-many-folders example.

Where we used to spend some time educating users was in:

  • The Deleted Items folder is not a filing-cabinet. In fact, empty it! Here's how to set up an auto-delete process...
  • When setting up an out-of-office rule, here are some guidelines.
  • This is what you can do when you get the "your mailbox is too big" emails.

In brief, we focused on pain areas. We didn't care if a user created one folder per day to put a day's correspondence in, or if they just left it all in Inbox and searched whenever they needed something (gmail-style!).

  • Deleted Items We actually had users who got rather cranky when we did a system-wide flush of deleted items during a migration. So we wrote some stuff to discourage using the trash-bin as a filing cabinet.
  • Out-of-office rules The grand-high-sysadmins were getting tired of handling helpdesk requests for de-tuning badly written OO rules, so we wrote some training on how to set up a good one.
  • Mailbox too big We had mail quotas, because we had to. So we wrote doc on ways to stay under. In time, our frequent fliers changed their mail-retentive ways.

The only standards we enforced were:

  • Keep your mail box down below a certain size (here are some ways to do that)
  • Don't be annoying with OO messages
  • Don't give out your mail password, even to your secretary. We mean it. Here is how you delegate...
  • What about sending large files? DO you do anything to help ease attachment storage? – ewwhite Jan 29 '13 at 1:22
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    @ewwhite Helpdesk FAQ on what our max sizes are. We tried to mirror what the big systems allowed to minimize friction ("You can't even send it to Google, so why are you complaining?"). – sysadmin1138 Jan 29 '13 at 1:32
  • Also, what did you put in place to discourage filing mail into deleted items? – ewwhite Jan 29 '13 at 12:19
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    @ewwhite First, we migrated everyone to Exchange 2007 which flushed all the trash-bins. Cue wailing and gnashing of teeth. Our Helpdesk folk spent time educating the biggest gnashers and helped them set up better sorting and auto-archiving. Second, any time someone complained about not enough mail-quota, we sent a minion down to look; and if they didn't have auto-archive set up we helped them do that. A lot of hand-holding, sure, but tenured professors require it. – sysadmin1138 Jan 29 '13 at 12:45

I like this analogy of your mailbox at home to try dealing with "bad" email users.

You don't leave all your unopened spam in your mailbox, you don't save your bills, your picture of your niece at the zoo, or anything else in there. You take it out and either throw it away, or put it somewhere else for safe keeping. Treat your email mailbox, like you would your home mailbox.

With that being said, user education and proper training goes a long way. We enforce mailbox limits within reason, and align send and receive size limitations with google's to avoid issues. Regardless, there will always be one user who thinks everything "should just work" without them having to deal with it (i.e. clean out your mailbox at some point in the many years of accumulation).

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    Interesting. What are the current Google Gmail limits? – ewwhite Jan 29 '13 at 16:02
  • Last time I checked they were 25MB send/ receive. We previously had ours set at 10MB which was causing issues when customers would get message from gmail or it's hosted domains. – HostBits Jan 29 '13 at 16:16

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