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ActiveSync keeps asking for password multiple times when syncing with Exchange

Posted on 2008-10-07
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Last Modified: 2013-12-05
Hi all,

I am having the following strange issue. I have a Windows Mobile 6.0 / 6.1 device (I have an Axim, a Samsung BlackJack II, etc). I have an Exchange Server 2007 running on Windows 2008, configured behind a NAT and RPC over HTTP with ports forwarded on the outside router (port 135 is blocked, but RPC over HTTP works fine). I am having an issue where NONE of my Windows Mobile devices "remember" the password.

The situation is as follows: when I run ActiveSync, it will prompt me for the password anywhere between 3 and 15 times or so. It seems it needs a password for EVERY step of the sync: Calendar, Email, Tasks, etc. When I enter the password, the sync progresses slightly. Eventually, if I enter it all the 15 times or whatever, it will stay synced and will sync perfectly by itself until I power off the device and power it on again.

The server is set up to authenticate using self-signed SSL+personal certificates; I have installed the self-signing CA's certificate onto the WM6 device, and installed a personal certificate on it as well (although I don't think it ever asks me to use the personal one).

What do I do? Any advice appreciated. It does not seem to be related to a specific Windows Mobile device - _all_ WM devices appear to behave this way with my servers.
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Question by:t00manyusers
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by:Cvif3v3r
ID: 22663820
Have you tried removing your Personal certificates and seeing if this corrects the issue? I use exchange 2007 for about 25 mobile devices and have not had this issue with but one of them. The old Q phone had an issue when we first started using them, but that was Windows Mobile 5. The personal certificates may be the cause of this issue. Try removing the requirement for personal certificates and if it functions correctly, rebuild your personal certs.
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by:t00manyusers
ID: 22664418
Hang on, are you saying I should remove the _requirement_ for certs, or I should remove the certificates itself from the Windows Mobile device? If you mean remove the _requirement_ from Exchange - how should I do it?
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by:t00manyusers
ID: 22680657
Any help, anyone?...
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Cvif3v3r earned 500 total points
ID: 22680673
If you remove the requirement for certs and it works you have eliminated the possibility of errors on the exchange server regarding aActive Sync. Then you are left with troubleshooting the certificates. Just a thought.
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Author Comment

by:t00manyusers
ID: 22810056
Sorry about the delay - was travelling, didn't have a chance to get back to this. Having set the certificate requirement to "ignore" from the previous "accept", it seems to no longer harrass me about passwords. Thanks for the thought!
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