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Outlook Error: could not open one or more attachments

Posted on 2004-10-13
Last Modified: 2011-08-18
Using outlook 2000 sp-3 I am no longer able to send any attachments without receiving the message "could not open one or more attachments"
After acknowledging this error msg the mail goes out with attachment, but it's very inconvenient.

I checked the knowledgebase and followed the suggestion to change security settings, but to no avail. (it's standard 'medium' now). I don't have a virusscanner installed and it does not matter which extension or size the attachments have. I'm completely sure I have no virus on my pc.

Originally I also had a problem receving attachments (a message came up that I was out of memory when viewing incoming messages in the preview pane), but after reinstalling outlook 2000 from scratch this disappeared for a few days. However afterwards it was just the way it was before. The problem with outgoing attachments stayed after the reinstall.

A second (related?) problem is that a new rule I made in Outlook (to forward all mail addressed from one mail address to another one) fails after sending about 10 to 20 messages due to it being 'out of resources'

I'm running XP sp2, but the problem was already there with SP1. The problem didn't always exist; it just popped up after about a year on this pc. My *.pst file is fairly large (almost 500mb)

I'm at a loss for an answer as neither the microsoft knowledgebase nor google come up with a satisfying link. Most point to problems with virusscanners.
Question by:max3d-nl
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LVL 49

Expert Comment

ID: 12298690
Hi max3d-nl,

Probably those are 2 different issues that you have got but let us tackle the first one

What type of email account you have setup in your outlook pop3,imap or exchange ?

Do you get any error message in your send/receive dialog box whenever the email with attachment sending fails ?

Do you see that the emails are getting stuck in the outbox?

Have you tried to recreate the email account by deleting and creating it fresh to see if that would solve the issue

have you increased the server timeouts in the properties of the email account to see if that would help solve the issue

DO these aswell

a) Open outlook .Go to help menu and click "Detect and repair". Check if this would help.

b) Repair PST : http://www.slipstick.com/problems/scanpst.htm

Post back

LVL 49

Expert Comment

ID: 12298705
have you already checked these MS KBs

OL2002: Outlook or Outlook Express Hangs After You Send an E-Mail Message That Has an Attachment

Operation Failed" Error Message When Sending Attachments

LVL 49

Accepted Solution

sunray_2003 earned 250 total points
ID: 12298737
Have you tried to send the email in different formats like Rich text, Plain text or HTML to see if that error would occur in all three formats ?

Have you already done updates on your outlook ??

Do you have any Anti-spam or Firewall installed on your machine and Have you temporarily disabled them to see if that would help

Have you got any add-ins installed in your outlook

There could be a simple profile corruption so create a new profile , setup the email account in there
and then check if that would solve the issue. If it solves , you have to recreate your old profile

Post back how it all goes

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LVL 21

Assisted Solution

traval earned 250 total points
ID: 12298912
Check if the problem is caused by a corrupted add-in or Outlook cache files.

1. Run Outlook in Safe Mode.

(a) Click Start, and click Run.
(b) In the Open box, type: "Outlook /safe" (without the quotation marks) There is a
space character between Outlook and the forward slash (/).
(c) Click OK.
(d) Perform a test.

2.  If the problem occurs in safe mode as well skip to step 3.  If it doesn't occur in Safe Mode we should disable the corrupted add-in.

(a) Open Outlook in Safe Mode (Outlook /safe).
(b) Click Tools->Options->Other->Advanced Options->Add-In Manager
(c) Check all the check boxes to enable all Add-Ins, and then click "Ok".
(d) Click "Ok" for two times.
(e) Click Tools->Options->Other->Advanced Options->Add-In Manager
(f) Clear all the check boxes to disable all Add-Ins, and then click "Ok".
(g) Click "Ok" for two times.
(h) Open Outlook in normal mode. All add-ins should be disabled at that time. If
the problem persists, please skip to Step 3.
(I) Click to enable one add-in and then restart Outlook to check if the problem
(J) Add one check back each time to the list of Add-In, restart Outlook, and repeat
the above procedure.
(k) Once the issue reappears again, you can determine which add-in causes this
problem and then disable it to solve the problem.

3. If the problem still occurs, it is possible that the Outlook cache files are corrupted.  Close outlook and take these steps:

(a) Perform a search on your computer to find the following three files:
NOTE: Some of them may not exist, but it doesn't matter. You may also need to show the extension of the file and enable the "show hidden files" option in the "Folder Option...".
(b) Right-click the file and rename the files to the following names:
"extend.dat" To "extend.old"
"outcmd.dat" To "outcmd.old"
"frmcache.dat" To "frmcache.old"
“views.dat” To “views.old”
(c) Perform a test to check if the problem is solved.

Author Comment

ID: 12299572
Well guys, thanks for all the suggestions. I had a busy time checking them all, but I'm just finished. The sad story: none was succesful. I'll resume them below. I went from latest to first suggestion.

-safe mode did not help

-renaming of dat files did not help (should i rename them back??)

-sending as rich text does not help

-diabling spampal did not help

-no firewall installed

-no add-ins installed

-all available updates from microsoft for outlook / office are in place

-Operation Failed" Error Message When Sending Attachments
http://support.microsoft.com/default.aspx?scid=kb;en-us;289966 is not relevant for my problem as I have Outlook open

-OL2002: Outlook or Outlook Express Hangs After You Send an E-Mail Message That Has an Attachment
http://support.microsoft.com/default.aspx?scid=kb;en-us;315008 is not relevant for my problem (outlook does not hang; it sends the attachments)

-detect and repair option in help did not help

-have you increased the server timeouts in the properties of the email account to see if that would help solve the issue. Yes, did not help.

-I did use the inbox repair tool: my pst file is oke.

-new profile? I have several mail accounts in Outlook. They all behave in the same way.
I recently moved to another mailserver and recreated some accounts. Again no change. Is this an answer?

-I'm using the Pop3 protocol.

For absolute clearness I'll repeat part of my original question. I have no actual problem sending these attachments. They go out well, but as soon as I attach them I get

the annoying errormsg and I can't see the attachments. After sending them I see the attachment icon in sent items, but if I open these I get the same errormsg. Strangely enough I get the errormsg twice for each attachment. The attachment itself won't open. So I just have to guess and hope that I sent the right one.

If I'm opening mails from others with attachments, I get the error: "could not open one or more attachments. Out of memory or system resources. Close some windows or programs and try again" Rest assured that I have checked with only Outlook running but the same result. The machine has 512 mb memory and lots of free disk space on C: and D:  

Author Comment

ID: 12299667
If forgot to say that after this last errormsg when opening mails from others with attachment, the attachment does open.
LVL 49

Expert Comment

ID: 12302056
Are you saying your issue is solved ?

Author Comment

ID: 12302197
No, no. I just didn't finish the sentence correctly.
I should have stated: "If I'm opening mails from others with attachments, I get the error: "could not open one or more attachments. Out of memory or system resources. Close some windows or programs and try again" I then have to click on this error msg and the attachment opens. So it's all a major nuisance, but in the end run I can send attachment and I can read them. Outlook just doesn't believe it.

Author Comment

ID: 12868510
It's a pity that nobody seems to know an answer. The problem still exists.
LVL 21

Expert Comment

ID: 12870334
I am suspicious that it might be a corrupted profile, like SR mentioned above, but you might be running in Internet Mail Only on Outlook 2000 so creating a new profile is not quite as simple as if you are running in Corporate/Workgroup mode.  You can check in Outlook under HELP->ABOUT to see if you are not sure.  If you want to continue troubleshooting write back with which mode you are running in.

If it's not the profile, normally I'd recommend the "sledgehammer" which is listed below.  My guess is either that one or more of the files listed below have either become corrupted or were replaced by a 3rd party application.  Let's check the profile before proceeding with these steps, unless you just have some free time on your hands.

1.  Backup all needed data for all Office applications.
2.  Run Selective Startup in MSConfig to remove possible conflicting applications.
3.  Uninstall Office 2000 (both disks if applicable)
4.  Download and run the Eraser2K utility (Q239938) http://support.microsoft.com/default.aspx?scid=KB;EN-US;239938 
5.  Remove the C:\Program Files\Microsoft Office folder.
6.  Backup and delete the following registry keys:
7.  Make sure you can view all hidden files.
8.  Delete (or rename) the following files (some may not be there - that isOK)
9.  Reboot the machine.
10.  Repair Internet Explorer vis the control panel.  If this is not available, due to it being installed with the OS, then uninstall and reinstall Outlook Express.
11. Reinstall office.
12. Cross your fingers.
LVL 49

Expert Comment

ID: 12870410

I like your detailed troubleshooting technique. Will you mind if I use it in some questions that regular repair or reinstallation doesnot work .. Ofcourse, acknowledgement to you , will be there


Author Comment

ID: 12888514
Sorry for reacting so late, traval. Will try your suggestions a.s.a.p., but it will take some days due to work load
LVL 21

Expert Comment

ID: 12900549
Sure SR, use away.  I keep alot of stuff like that in cliptray to save time.

Author Comment

ID: 13469935
I guess these guys deserve some reward, but it's still a pity that I never got a real solution. The approach from travor (delete everything officelike and reinstall) is just brute force.

Author Comment

ID: 13469939
I meant traval instead of travor. Sorry about that.
Anyway I lost my 500 points without getting any solution to my problem.
LVL 21

Expert Comment

ID: 13477337
If you want to request a refund I have no objection, assuming SR doesn't object either and the admin's agree, take the points and open a new question for this, since this one is 6 months old and buried under all of the newer questions.  That said......

Regarding the problem/resolution, if one of your mapi files was corrupted or replaced by a 3rd party app, the method I described will resolve that by replacing all mapi files, rather than 1 at a time trying to determine which one caused the problem.  What woudl count as a "real solution"?

Additionally, both SR and I suspected this was a profile problem, and I explicitly said I felt you should investigate that before going thru the complete uninstall/reinstall in these statements from above:
"I am suspicious that it might be a corrupted profile, like SR mentioned above, but you might be running in Internet Mail Only on Outlook 2000 so creating a new profile is not quite as simple as if you are running in Corporate/Workgroup mode."
"You can check in Outlook under HELP->ABOUT to see if you are not sure.  If you want to continue troubleshooting write back with which mode you are running in."
"Let's check the profile before proceeding with these steps, unless you just have some free time on your hands."

Finally, you have abandoned this problem twice for over 2 months each time.  While SR and I are trying to help, and are happy to do so, this is your technical problem and it is your responsibility to keep this problem current and updated.  While I can understand you are busy and unable to devote time to this frequently, hopefully you can see why it is assumed the problem is resolved when it is abandoned rather than assuming it is not resolved but the poster is simply not responding.  Also, per http://www.experts-exchange.com/help.jsp#hi78
"the Moderators and Page Editors consider abandoning questions as a violation of the Membership Guidelines, specifically the clause regarding "abuse of the points system", (any question that has not had a response in 21 days or longer is considered abandoned)"


Author Comment

ID: 13481172
I appreciate your time and attention and have no problem with a reward. I was just frustrated that I'm still stuck.

To be precise: I didn't abandon the problem twice. I gave answers to all (very helpfull) suggestions afaik until 10/13. When it was proposed the first time to close the question I stated that I still had the problem.

It's true that I didn't follow up on my own comment that I would try your 'sledgehammer'. I couldn't find the time to do this very thorough way of getting rid of the original install of MS office. I am pretty sure it would work as it leads to a new install of MSOffice. I didn't consider it a solution as it's comparable to 'reformat the disk and start again'. It does the job, but it's not satisfying from a technical point of view.

What I missed was your suggestion of the profile question. SR asked it first and I answered him with a uncertain '-new profile? I have several mail accounts in Outlook. They all behave in the same way.I recently moved to another mailserver and recreated some accounts. Again no change. Is this an answer?" He didn't correct me, nor did you, so I assumed this was out of the way.

Today I finally understood what you guys meant in the first place. I'm running in Internet Mail only, so I created a new userprofile on this machine and configured the existing Outlook 2000 for it. If I log in as this different user the problem with attachments is gone.

Does this help in any way? Is there a way to repair the old profile without completely deleting Office?

Thanks in advance.
LVL 21

Expert Comment

ID: 13481565
Regarding reinstalling, if your definition of a solution to this problem means accurately diagnosing what the cause of this problem is and why it occurred, then I feel confident wagering that you will never find a satisfactory solution.  This type of problem doesn't lend itself to diagnosing causes.

If, on the other hand, you define a solution as the annoying error no longer occurring when you send attachments then we can certainly fix it.  I do appreciate your opinion about (and feel pretty annoyed with) the "format as a first troubleshooting step" bunch of so called experts we see these days, but I feel we've put in due diligence on this one.  It's not always a "give up" to completely remove and reinstall, you just use that as a last resort which I feel we were rapidly approaching, if the profile wasn't the problem.

Since the profile is a suspect, you can try troubleshooting the old profile in your original Windows Profile, to see if this resolves the problem:
1.  Open Outlook, go to TOOLS->ACCOUNTS and for each mail account click EXPORT and save your account settings to the desktop.
2.  In the folder list right click "Outlook Today - Personal Folder", choose PROPERTIES then ADVANCED and make note of the file name/location.
3.  Close Outlook, click START->RUN and type in "outlook.exe /cleanprofile" and click GO
4.  Outlook will start in a new, empty profile.
5.  Click TOOLS->ACCOUNTS and import the data from your desktop.
6.  Test sending email with attachment to self to see if problem is resolved.  If so..
7.  Click FILE->IMPORT&EXPORT->IMPORT FROM FILE->PERSONAL FOLDER FILE and point to the file you located in step 2, finish wizard to import the data into the new profile.

I understand your semantic arguments regarding the definition of "abandoned", but Experts Exchange considers a case abandoned if it is left open with no activity for more than 21 days.  This has occurred twice.  I'm not saying this as an accusation or anything, I'm just explaining why the case has been thru the auto-close phase twice, the final one actually resulting in the case closure.  The admins are just trying to keep the place neat.

Author Comment

ID: 13486818
I followed your instructions, but at 4) I didn't start in a new, empty profile.
I still had my old accounts and mailbox. I checked if there were multiple outlook.exe's on my system, but no. When I tried it again with the full path to outlook.exe (as in C:\Program Files\Microsoft Office\Office\outlook.exe" /cleanprofile, so with a different position for the " because of the space in the pathname) it gave the same result. Several variations later I still have the old profile.

Just to check that I was able to use command line switches with OL correctly, I tried outlook.exe /folder. This had the expected effect.

I'm at a loss here.
LVL 21

Expert Comment

ID: 13487496
OK, let's try this manually:

1.  Quit Outlook if it is running.
2.  Click Start , point to Settings , and then click Control Panel .
3.  Double-click the Mail icon.
4.  Click and then remove each of your mail accounts.   NOTE : Make certain you know all of the required settings before you remove any of these accounts.

Now with no accounts configured in Outlook, start Outlook and try opening an attachment in your Sent Items folder, or in an email you received from someone else, and see if the error still occurs.

If not then add each account back from the Mail icon on Control Panel, restart Outlook, and try to send a message with an attachment.
LVL 12

Expert Comment

ID: 13487577
I would add one additional step.  Once ALL the mail accounts have been removed - also remove the mail profile.

Once that is complete then you may begin to setup the profile and accounts again.
LVL 21

Expert Comment

ID: 13488395
Unfortunately removing the profile is not an option in Internet Mail Only installation.  We have already determined that a new Windows Profile resolves the problem but want to fix the old Windows profile.

However, if the account removal/reinstallation doesn't work then we can try switching your Outlook installation to Corporate/Workgroup instead of Internet Mail Only, assuming you have your CD handy.  This will give us the option of creating a new Outlook profile in the old Windows profile.

Author Comment

ID: 13489051
I tried the remove all accounts experiment. Without any accounts I was still unable to attach an attachment.  I have re-imported the accounts again.
LVL 21

Expert Comment

ID: 13489908
OK, we can try to create a new outlook profile in your old windows user account, by switching to Corporate/Workgroup.

1.  On the Tools menu, click Options .
2.  On the Mail Delivery Tab, click Reconfigure Mail Support .
3.  On the E-mail Service Options page, click to select the Corporate/Workgroup mode. Click Next.
4.  Read the warning message and then click Yes. Outlook will close.
5.  Start Outlook. The Windows Installer will start and install the required files.

Now try opening Outlook normally and see if you get the error message with attachments.  If so, here are the steps for creating a new profile in Outlook 2000 C/W.  Do not delete your existing profile until you verify the new profile doesn't have the same error.

1.  On the Control Panel Double-click the Mail or Mail and Fax icon.
2.  Click the Services tab, then click Show Profiles to list your profiles.  Choose to have Outlook prompt for a profile when starting.
3.  Click Add to start the Inbox Setup Wizard.
4.  Click Manually configure information services, and then click Next .
5.  In the Profile Name box, type a name for the new profile.
6.  Click Add , and then choose a PST file and Internet Email account to add to the profile.  Configure the account to send/receive thru one of your accounts.
7.  Start Outlook and see if the error still occurs.
8.  Start to think to yourself that uninstalling/reinstalling might not be so bad after all (just kidding)

Author Comment

ID: 13494574
I followed all your instructions in detail and the only thing that changed is the wording of the error msg. From 'Could not open or more attachments' it became 'Out of memory or system resources. Close some windows and try again. ' This toggles depending on the internet only e-mail or Corporate mode.

In the end I do agree with your point 8 and Iam ready to surrender. Thanks a lot for al your detailed help. If I could I would give you the majority of the points for trying so hard to help, but it's no longer up to me.

If the topic is still open when I'm finished reinstalling as per your instructions I will post the result.
LVL 21

Expert Comment

ID: 13496667
OK, if the problems are continuing in a newly created profile after switching to C/W mode, then it's quite likely some of the MAPI files mentioned above.  There are two other quick things you can check before completely uninstalling/reinstalling:

1.  If you are running PGP encryption uninstall that and test again.

2.  Verify that the registry key below is set so something like this:
Key:  HKEY_CURRENT_USER\Software\Microsoft\Office\9.0\Outlook\Security\OutlookSecureTempFolder
Value: C:\Documents and Settings\<username>\Local Settings\Temporary Internet Files

Author Comment

ID: 13499982
Well, this afternoon I bit the bullet and got rid of the existing office installation as per the detailed instructions of Traval.

In the process I encountered some problems which I will detail for future reference:

1) Eraser2K is not functional under Windows XP
2) the alternative manual approach as recommended by microsoft (http://support.microsoft.com/default.aspx?scid=kb;nl;219423) is very, very labour intensive. It requires deletion of hundreds of files.
3) I stopped trying to follow the msoft approach when I saw that XP either refused to delete some dll's (they were in active use) or reinstalled them automagically seconds after I deleted them. Even when I started without any startup programs/utilities and every program closed most of the recommended files could not be deleted.
4) I went back to your sledgehammer list and carried out the points 5, 6, and 7 succesfully
5) your list of files to delete also proved quite labour intensive as I had to do a search for every filemask you listed
6) some I did find and they could be deleted
7) however lots of them where either false hits (like 'outlinetools.dll' where you specified outl*.dll), multiple occurences of the files (f.i. in rollback folders or restore points) or they just didn't exist (the majority). I would recommend that you make some more detailed recommendations about the first two points as they are prone to lead to system instabilities when carried out by someone who doesn't know what he is doing

After working through all the points on the list I reinstalled office. First test mail with attachments was succesfull. Hurray! Lots of work, but the reward was there.

Quickly I proceeded to the automatic update tools online with Microsoft. After the first required separate update for Office 2000: SR-1A, I retested. The problem was back! Just to be sure I proceeded to install the SR-3. Problem still there. The last update (for Outlook 18 dec 2002) did not fix it either.

So I'm back where I began. Good thiing I was so prudent to test the first clean install from CD. The problem seems very simple to reproduce.  Just install SR-1A and it's there.

Two questions remain:
- why am I the only one where the SR-1A update creates this problem.
- how to circumvent this bug. Without upgrading to the latest servicepacks the office 2000 package is not usable for my purposes.

Looks like I will have to upgrade to a later office suite, but that will break a msaccess application which I need. Catch22 here.

Author Comment

ID: 13499994
Forgot to tell: after the upgrades I checked the two latest suggestions of Traval. I don't have PGP installed and changing the registry key (it's value was \OLDK\) to his recommendation didn't help.
LVL 21

Expert Comment

ID: 13500369
Sorry, for Windows XP I should have pointed you to this article instead of Eraser2k, the msizap.exe does the trick normally.
Description of the Windows Installer CleanUp Utility

Does Outlook Express open without error?  
1.  If not then we need to reinstall Outlook Express
2.  If so, click FILE->IMPORT->MAIL ACCOUNT SETTINGS and follow the wizard to import your account info into OE.  Open an email, address it to yourself, and attach a file or two and try sending it to see if you get an error.

Author Comment

ID: 13501414
Outlook express 6.0 was fully functional without any reinstall.
After following these instructions I had no problem sending an email with attachments with OE.
LVL 21

Expert Comment

ID: 13507852
Just to verify, there is still no anti-virus software of any kind on the computer that might be interferring?

Go to TOOLS->OPTIONS->SECURITY, so you have an "Attachment Security"?  If so is it set on NONE?  If not set it on NONE and try reproducing the problem.  Setting this on High should trigger a warning, not an error message, but who knows?

You might also want to try downloading this utility to see if we get any more information:

Author Comment

ID: 13511665
Thanks for your suggestions, however...:

Still no anti-virus software (and never got a virus in more than 10 years).
I don't have an 'Attachment Security' item in 'Security'
I already use the Web alerts utility, but to no avail.

LVL 21

Expert Comment

ID: 13512026
OK, the no "Attachment Security" button means that the Outlook 2000 Email Security Update has been installed.  I thought that it was in SP1 but wasn't positive.  But it removes the "Attachment Security" button among other things.

This is the only change I can thing of that would be causing this difference in behavior with attachments between SP0 and SP1.

Since the problem already existing, do you mind installing either SP2 or SP3 so we can see if this security feature is causing this?  If you don't mind walking thru this, after installing either SP2 or SP3 you would:

Open RegEdit and verify this key exists:
Add a new value called "Level1Remove"
Right-click the new Level1Remove and choose Modify
Enter the extension you are using for testing, if more than one seperate with semicolon like this ".exe;.com"
Click OK, Quit Registry Editor, and Restart your computer.
Try opening or sending an attachment of the type you specified.

Author Comment

ID: 13514298
I already was running SP-3. See my comment of 03/09/2005 12:17PM PST.
However I followed your suggestion and added this registry key with "*.txt" as a testing extension. Restarted and ....
Now I am able to send any attachment without any error msg!!! Not only *.txt, but all the other ones as well!!! I can open mails with attachment without warning as well.

It seems like this last registry adjustment (with only *.txt) fixed the problem! If I understood why I would be a truly happy guy, but even without I'm very satisfied. Thank you so much Traval!

LVL 21

Expert Comment

ID: 13517371
Oh man, we fixed it?  Bummer!  Now what are we going to do with our days?  ;-)

Author Comment

ID: 13518409
Finding a logical explanation :)
LVL 21

Expert Comment

ID: 13518651
Thanks but no thanks, it's time for me to move on with my life.  Asta la vista.

Expert Comment

ID: 14992828
Just wanted to let you guys know that I just had a user with an extremely similar problem here.  He could not open a specific .pdf file when sent to him as an attachment.  Other .pdf files opened just fine, but not this particular one. (To clarify, our system sends out "ROBOT" reports to our sales people daily, the affected file being one of them.)  Other users had no problem opening this file, just this one user.  Anyway, I wanted to report that I tried many of the suggestions (saving "sledgehammer" for last, of course) to no avail until I tried traval's registry suggestion:

2.  Verify that the registry key below is set so something like this:
Key:  HKEY_CURRENT_USER\Software\Microsoft\Office\9.0\Outlook\Security\OutlookSecureTempFolder
Value: C:\Documents and Settings\<username>\Local Settings\Temporary Internet Files

My user had the following:
Value: C:\Documents and Settings\<username>\Local Settings\Temporary Internet Files\OLDK6\

I stripped off the "\OLDK6\" at the end of this string, rebooted, and it worked!!!

Thanks, traval, I am putting away my sledgehammer before someone gets hurt(probably me)

Expert Comment

ID: 20052435
Click on Addins One by One
Change LoadBehavior Value to 0&

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