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Microsoft Oulook password prompt keeps on prompting me for my password

i am running windows 7, with outlook 2010, and excahnge 2007, SP2.
A few weeks ago, for some strange reason, the attached screenshot has started popping up every time I start outlook.  It's also happening to other users as well. This started a few weeks ago, and I don't know why or how to fix it. Possibly a windows update, I don't know?
Even if I check the checkbox to remember my password, it still prompts everytime I start outlook.

In the past, it hasn't before, so I don't know how to fix that.
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Dan
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Hi, The date on your certificate may have expired.
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so where do I find the certificate and how do I fix it?  I believe with exchange, I just used the built in one, I didn't purchase a cert.
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no, exchange is on windows server 2003 R2 64bit, and my outlook is on win 7.
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If its SBS replace default web site for SBS Web Applications in IIS
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I only have IIS6, so I don't have IIS7.  How do I view the cert in IIS6?
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actually, I figured it out, it's valid until 2013, and I do have an external certificate, it' not the server default. It's registered with godaddy.
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Thanks everyone for your assistance, I can't believe I didnt' think to look at the outlook anywhere settings, as it was turned on.  I use it on my laptop, but not on my desktop.  Turned it off and it doesn't prompt me anymore.
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IT Guy

ok so new development; when users are at home and the VPN into their work PC; if the RDP connection times out the pc Logs them off