Summary: Outlook Express is a very popular desktop email program. Unfortunately, it can be touchy about its files, particularly when it comes to compaction.
About 6 months ago I started getting a message (apparently from Outlook Express, but even when OE is not running) saying "To free up disc space OE can compact messages. This may take up to a few minutes. -OK/Cancel". This has become very invasive and, even after OKing (and losing use of the commuter for several minutes), can pop up again within seconds/minutes and re-pop up within seconds of being canceled. Cause and cure? I've deleted a lot of spam and deleted messages in case these were the trigger.
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My honest opinion?
Change email programs.
I'll discuss that option, the bug that you're seeing, and what you might do. But first, I'm going to spend a couple of minutes explaining why I hold that opinion.
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I don't recommend or disrecommend products lightly. But what I will do is pay attention to the experiences of the users that post questions here on Ask Leo!.
Outlook Express is a fine, fine email program. Because it's free and available on every copy of Windows XP, and came free with Internet Explorer prior to that, it's a very popular email program.
Unfortunately, more people report more problems and lost mail to me having used Outlook Express than any other desktop email program, hands down. Next to losing all your email in a free email account, it's probably my biggest source of email related data loss stories.
The most common culprit is, in fact, the very database compaction that you're asking about. I'm sure it works well for many, if not most people, but when it fails it can be disastrous. Even backups can be problematic because Outlook Express is so touchy about the files and format of its email database.
And that, perhaps, is the underlying problem: Outlook Express uses a proprietary and apparently very touchy database format to store your emails. While there are third party utilities, often expensive ones at that, to recover, it's simply not a particularly robust set up.
It's hard to move, hard to recover, hard to repair and apparently easy to break.
But it's free. 
The good news is that there are so many alternatives now, including free programs like Thunderbird that have almost everything Outlook Express does, that if it's at all feasible I recommend jumping ship at the first sign of trouble. If not before.
With that out of my system...
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I recommend you read this thread out on the Microsoft public discussion group. There you'll find all sorts of recommendations that boil down to:
Compact regularly, or you may suffer database corruption.
If you're up to date, OE will auto-compact after every 100 shut downs if you haven't.
Never interfere with the compact process or you may suffer database corruption.
Don't get too fancy in your folder organization or you may suffer database corruption.
Disable your anti-virus programs scanning of email and email files, or you may suffer database corruption.
Don't let your folders get too big or you may suffer database corruption.
Backup, backup, backup in case you suffer database corruption.
As I said, for many, many people Outlook Express works, and works well. But in my experience fielding questions and hearing of problems, as soon as your own needs start to get more sophisticated in just about any way, it's time to move on.
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A note about Windows Mail - the Outlook Express replacement on Windows Vista - and Windows Live Mail - the Outlook Express replacement you can download free from Microsoft.
My feelings on these guys are mixed. They have both apparently abandoned the problematic data store format used by Outlook Express, which in my opinion is great news. It's still proprietary, but hopefully more robust and recoverable.
However given that there are free alternatives with a stronger track record, if you're considering a move I'd be much more tempted to move to these as more reliable "known quantities".
Related:
How do Outlook and Outlook Express relate? Even though they share similar names and do similar things, Outlook and Outlook Express are actually not related to each other at all.
What's the difference between Windows Mail, Windows Live Mail, Windows Live Hotmail and MSN Hotmail? Microsoft has created a lot of confusion with how it names its mail products. Add the transition from MSN to Windows Live branding and it gets worse.
Thunderbird - A Free, Open Source, and Powerful Email Client Thunderbird is a robust and powerful email program that can meet the needs of both light and power users. I use it all day every day.
Microsoft: The Other E-Mail Threat: File Corruption in Outlook Express
Article C3802 - July 10, 2009
NOBODY seem to have answered or even addressed the second question - how do I get it to stop asking me ?
Posted by: Robin Clay at July 18, 2009 2:52 PMNot even the MicroSoft thread whose URL is given.
Robin, Josie F answered that question. July 14, 2009. 3:30 p.m.
Posted by: Edward Richter at July 19, 2009 5:41 AMEdward Richter,
For info about "Mail clients in Vista and Windows 7" go to http://aumha.net/viewtopic.php?f=7&t=36767 which includes the following link to program for creating identities in Windows Mail:
http://www.oehelp.com/WMIDs/Default.aspx -- go to its home page http://www.oehelp.com/ for other programs including DBXtract, which I have used successfully in the past when my OE was corrupted.
If you really want to keep OE, perhaps you could go back to an earlier version of Internet Explorer, with which OE was bundled. (These are available at http://www.oldversion.com/ and http://www.oldapps.com/ and probably other locations as well.) There could be other problems with that, of course, including security ones. Perhaps Leo or someone more knowledgeable could comment on this idea, especially as I have no experience with Vista or Windows 7.
(In fact, although I am typing this on my husband's XP machine and I used XP at work for five years before retiring, on my own PC I am still using 98SE and of course the accompanying OE 5.5.)
Merna
Posted by: Merna B. at July 19, 2009 9:18 PMJosie, I went to Kellys Korner and spent a half hour looking for the download that you suggested for resetting the counter to zero. Where is it hiding??
Posted by: Ken Hall at July 20, 2009 3:20 AMKen Hall,
See No. 367 in lefthand column at http://www.kellys-korner-xp.com/xp_tweaks.htm (found by Googling). I can understand how you could have spent half an hour or even MUCH longer trying to find it by simply looking around Kelly's Korner. I tried using the Search facility at KK's home page and got no results -- found the answer by doing a Google search for "compactcheck.vbs".
Merna B.
Posted by: Merna B. at July 20, 2009 7:11 AMKen Hall,
A P.S. to my previous message. My Google search produced twenty-seven results ( at http://www.google.com.au/search?hl=en&q=%22compactcheck.vbs%22&meta=lr%3Dlang_en&aq=f&oq= ).
I looked at only the first two to find the location at Kelly's Korner, but those results also indicated that the script does not necessarily solve the problem of the compacting required message.
Merna B.
Posted by: Merna B. at July 20, 2009 7:19 AMI read the question about the Outlook Express compaction message, which just lately I have been getting. I have NEVER used Outlook Express (just Outlook), and have never said "OK" to the message, just canceled out of it. How do I stop it from appearing?
Posted by: Marianne Rankin at July 22, 2009 11:57 AMThe first comment I see is Johnny's, dated July 15, so I cannot find Josie's note on how to get it to stop asking me dated July 14. How can I find it?
24-Jul-2009
Posted by: Marianne Rankin at July 23, 2009 9:11 PM
Windows Desktop Search (WDS) 4.0 (Windows Search)is causing this problem when it constantly searches OE. I understand that Nero can also cause this. WDS 4.0 was delivered in Windows Update a while back. The message even happens when you don't use OE (Outlook Express). Uncheck the box in WDS that says to search OE. Then shut down everything you can, use a backup program such as https://www.idrive.com/p=idr101 and allow the compaction. OE compaction (IE7) will save big folders before compacting them, and they are later in your deleted items folder. I have the WDS problem. I have used Outlook Express for years, and have not had a problem in a long time. I have emails back to 1998 or earlier, and a huge inbox, plus 3 identities. I had a problem with Netscape in 1998, I believe it was, and OE was able to import in the mail when Netscape would not start. I also exported in everything at home when I left work. In OE, if you damage a folder, you can just put it back - each folde has a .DBX file. If you delete a folder, just add it back, and restore the original folder from a backup. The problem is that any time the OE folders are searched, the change date is altered since the folder is opened, and that causes incremental backups to be invoked by backup programs after a find is done in OE. (This might have been fixed in IE8, but I don't know - OE ships with IE. WDS does a great job searching fast, but I am unchecking it for OE searching to stop this problem until it is fixed. There are other OE search programs, and I might try that. Good Luck! -J. Weinberg
Posted by: J Weinberg at August 25, 2009 11:12 PMI found your site after searching for help. I just finished compacting my mssgs in OE, opened my email--my sent box completely empty, went to recycle bin, rt clicked on sent.bak, clicked restore, that disappeared and did not restore!! I can't find it anywhere...very important info (and no, I haven't been backing up my email files, which was a huge mistake that I won't make again, but that doesn't find my files now...). Yes, my windows updates are all up-to-date and I religously run my BitDefender virus and spyware scans. Thank you for any suggestions you may have.
Posted by: lisa at September 17, 2009 3:03 AM