Entourage Boots Me From Exchange Server Constantly


I am running Entourage 2004 on a g5 system 10.3.9. Connected to a microsoft exchange server. The configuration was set up automatically.

Entourage continuously logs me off the server then give the error :

“The server for account "Exchange Server" returned the error "Logon failure: unknown user name or bad password." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?””

I deleted any keychains from all areas of the system which did not resolve.

I also updated entourage thinking it may be a bug.

Our IT help has no clue on this one but from my research I can see it is a pretty common problem

The boot happens approx every 10 minutes to 1/2 hour.


The first thing that you should understand is that Entourage 2004 is a bug. Having said that, it gets more complicated. You have access only to your Entourage front end. You have not a clue how Exchange is setup on the backend. My firm's Exchange server requires users to change passwords every 30 days, IIRC. My password is stored within my account settings in Entourage. When I change my password, it is updated within my Entourage account settings.

Again without access to your particular system, it is impossible to diagnose your problem. However, I find you disconnect interval curious. Entourage updates its data every 10 minutes. You are being booted off every 10 minutes. Are you ever actually connected? Does your Exchange server have web-based access? If so, are you able to use it?

I am having EXACTLY same issue. You asked the initial poster if he/she had web based Exchange service and the question was never answered. Since I have the same problem, in my case my company does provide web based Exchange access and it does work, but I do have this problem.

The interesting thing is that if I access email with the web client before using Entourage, authentication succeeds. If I get the said error message again, refreshing the web page seems to 'fix' the authentication issue temporarily.
Hi all,

First off I am 3 weeks into my mac career after 10 in the PC world so please bare with me.

I am in a small office that is a mixture of Macs and pc's. only 5 are using entourage with exchange. 1 account has been having this logoff problem for 4 months. She has had to use the OWA (which works fine). she has about 700MB in her mailbox.

Mac OX 10..4.5
Entourage 11.2.5
Exchange 2003 on win2k3

All system are to patch. It would be probably easier to list the things I havent done. I will just go over a few.

these are in no particular order

created a new account on another mac with entourage installed and connected to the problem account from there. This was a brand new macbook with a fresh OS patched and entourage was installed
clean. no change. other accounts would work fine on this machine

tried a multitude of preference settings for entourage
deleted msentourage plist and entourage plist under /user/library/preference/microsoft. no change
disabled notifications, deleted some recurring calendar events.

After exhausting what I thought were my only options on the client side I focused on the server.

disabled always ask for digitally signed communications (server)
-this is to prevent smb man in the middle attacks. Its actually reducing my servers security level (macs seems to require those type of solutions). It did stop a lot of failure logs in the event log that were occurring but the problem still persisted. disable option leaves it up to the client to ask for signing. enabled netlogon logging;userenv logging
a few other suggested changes found throughout the net. no change

At this point i figured the mailbox was corrupt. I decided to extract the mail out of the suspect mailbox into a pst with exmerge. I created a temp account mailbox enabled and imported the pst into it. This pst contains all the mail,settings/calander/tasks and once imported to the new account will be a duplicate of the original mailbox....with a new owner of course. before the import I used MS scanpst.ese to verify the pst. it checked out fine.

lmao. that new mac comercial just came on..ugh...I want to seal him in his box and send him to the moon.

I honestly thought that I would logon to the macbook (the machine I used as an alternate logon to test the account) and the account i just created with all the mail from the screwed up account would work fine. Too my horror same old story. The only good thing now was I could work on the problem and still allow the user to work.

I began to purge everything...i deleted all calander events;pretty much every mail message;tasks;emptied trash. I was pretty much left with the address book. no change.

Then i decided to try empty cache. I selected the remote exchange server folder so all folders would be purged then click "empty cache" from the edit menu. I avoided this option because of the fear mongering under the help menu for its decription. Viola.....the account went from logging off by itself every few minutes to holding steady with no disconnects.

I have read up on its purpose. It essentially does a refresh. all the local mail/calendar/tasks etc that you see under your remote server folder is purged and downloaded again from the server.

I now had the temp account working. I decided to try it again. I went back and created a 2nd temp account mailbox enabled and imported the same pst file I imported to the first temp account. I created a new mac account and configured entourage on the same macbook. I thought that this account would then revert back to the login failures.....well its been running for the entire writing of this post. Its running fine with no logon failures. this account has the identical content of the original temp account and the origianl problem account.

This tells me that the problem account is tatooing the system you use to logon to entourage with and until the cache is emptied. This process does a variety of things that goes beyond refreshing the mail. I dont know it well enough to list its extra activities.

Its friday, so I wont get to try the real account until monday. I am interested if emptying the cache is the real solution. If anybody tries this please make sure your mailbox is backed up either on your server or thru entourage exporting. I tried a tonne of fixes this was defiantely the last one.

I am finding that mac support is lacking in a lot of areas. the solution or answer is wait for the patch. Maybe this is because IT groups doesnt like the headaches or extra responsibility so they dont offer support. At the same time the roll out of macs where i am is very liberal, admin access with very little little accountabilty with respect to maintenance. they want all this freedom but wont manage or clear out mail. Time to kick butt.