Outlook Anywhere

I have users that are continually being prompted for their credentials when using outlook anywhere even after ticking the box to save password. (This could happen 5 to 8 times each hour)
We are using Exchange 2010 and Oulook 2010.
What checks & actions could I perform to resolve this ?

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BusbarSolutions ArchitectCommented:
make sure that internal and external URLs are correct.
Also login using domain\username
if you are using TMG, make sure that listener configurations are correct.
DNRRPAuthor Commented:
Sorry what do you mean using TMG ?
What should I be looking for to determin when an internal & external URL's lool6 correct ? And where do you look ?
Also where do I check the listener configurations ?
As a certificate required for Outlook anywhere ?

BusbarSolutions ArchitectCommented:
Can you check the internal/External URLs in Exchange management shell?!

do you know how ?!
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DNRRPAuthor Commented:
I do not know how to check the internal/external URL's in powershell
Sivaraj ELead – IT InfrastructuresCommented:
Some basic security setting needs to checked, may be you need to enable NTLM authentication if basic authentication is in place, sharing those links below, please have a look.

Hold CTRL and press right click on your outlook icon on Taskbar.



Regards, Shiva

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Arjun VyavahareTechnical ConsultantCommented:
Open your firewall realtime traffic and check if anything is getting block when Outlook is trying to connect with exchange server.

based on shared error message it seems like there is issue with your firewall and also let me know outlook anywhere is working proper internally?

Md. MojahidCommented:
Check authentication setting and also try to reset password.
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