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KB21700 - Password prompted multiple times when configuring ActiveSync on Windows mobile with certificate check enabled in SA

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Last Modified Date10/22/2018 4:52 PM
This article describes the issue of the Password being prompted for multiple times when configuring ActiveSync on Windows mobile for the first time.

Problem or Goal


  • ActiveSync configured with Virtual port.
  • Virtual/external port is configured for certificate check in the SA under: System > Configuration > Security > SSL Options > Require client certificate on these ports enabled with corresponding port configured.

  1. During the initial configuration from Windows Mobile users will be prompted for the password multiple times; it is an expected behavior.
  2. After the Initial Sync is completed:
    1. If the user enables the save password option under ActiveSync configuration in Windows mobile, they will be able to sync mails without being prompted for the password.
    2. If the user did not enable the save password option, then the password need to be entered once to access e-mails.
Note: Being prompted for the password repeatedly, occurs even (without SA) when we access the Exchange server directly with both the Certificate and NTLM authentication enabled.
Related Links
Attachment 1 
Created ByData Deployment



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