Outlook 2007 Outlook Anywhere Does not remember password

I have a client who has a domain running SBS 2003 w/ Exchange 2003.  Outlook anywhere is configured and working.  At the client location there is a non-domain computer on a different subnet that accesses Exchange via Outlook anywhere.  Everything works fine, except that the user is prompted for a domain password every time when she logs in despite Remeber password being checked.  Outlook 2007 is set up to use NTLM authentication.  There is also a Sharepoint calendar linked to this Outlook.  The user has to enter domain credentials again for the Sharepoint calendar despite remember password being checked.  I have manually created cached network credentials for the domain account whose mailbox is being accessed for the specific server as well as for *.domain.local for domain\user with the password.  I have tried clearing the Application Data\Microsoft\Protect directory for the user's profile and then trying to cache the password again during the log into Outlook with no success.  

Any thoughts?  Getting to be very frustrating - At a minimum I'd like to eliminate the need for the user to enter the password twice (once for Exchange and once for Sharepoint since it's the same domain account for both).

Thanks,
Patrick

 
February 19th, 2015 2:27pm

I've seen some similar threads and the reason can be a lot:

Outlook Anywhere password Prompts

"You need to alter the default IIS & Virtual Directories settings. It can be performed by the following the steps given below:

1. Go to the settings in IIS7.
2. Select each Virtual Directory.
3. Then IIS section. go to Authentication  

All the Virtual directories requires SSL with 128bit except for OAB that don't need SSL and RpcWithCert which don't need 128bit (it don't need SSL though). "

Outlook Anywhere keeps prompting for Password

"It turned out to be the certificate... Outlook anywhere does not allow for Subject Alternate Names on certificates like OWA (Outlook Web Access), and OMA (Outlook Mobile Access) do. This company had the same dns name space internally as what they use externally, and registered their certificate to be that of the host name of their old exchange server!!! (yuck). In result I just ignored it and used a subject alternate name that of webmail which they also registered for all services. Bottom line - Outlook Anywhere will not use subject alternative names, only the correct issued to: name of the certificate. I did not find this documented anywhere!"

I hope this could be a bit of help.

-Jeff

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February 22nd, 2015 3:26am

I've seen some similar threads and the reason can be a lot:

Outlook Anywhere password Prompts

"You need to alter the default IIS & Virtual Directories settings. It can be performed by the following the steps given below:

1. Go to the settings in IIS7.
2. Select each Virtual Directory.
3. Then IIS section. go to Authentication  

All the Virtual directories requires SSL with 128bit except for OAB that don't need SSL and RpcWithCert which don't need 128bit (it don't need SSL though). "

Outlook Anywhere keeps prompting for Password

"It turned out to be the certificate... Outlook anywhere does not allow for Subject Alternate Names on certificates like OWA (Outlook Web Access), and OMA (Outlook Mobile Access) do. This company had the same dns name space internally as what they use externally, and registered their certificate to be that of the host name of their old exchange server!!! (yuck). In result I just ignored it and used a subject alternate name that of webmail which they also registered for all services. Bottom line - Outlook Anywhere will not use subject alternative names, only the correct issued to: name of the certificate. I did not find this documented anywhere!"

I hope this could be a bit of help.

-Jeff

  • Edited by Jeff Hardyy Sunday, February 22, 2015 8:26 AM
February 22nd, 2015 11:25am

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