Below are some of the steps you can use to troubleshoot Outlook login Prompt Issues
Step 1: Download and Install Netmon on the PC having the issue
1) Netmon 3.4 can be downloaded from herehttp://www.microsoft.com/downloads/details.aspx?FamilyID=983b941d-06cb-4658-b7f6-3088333d062f&displaylang=en
2) Install Network Monitor on the appropriate server/client.
3) Start the Network Monitor tool, there will be a shortcut on your Start menu under Programs. Right click and “Run as administrator” in elevated mode.
4) From the “Tools” -> “Options” ensure that the Temporary capture file size is set to at least 200mb on servers.
5) Start Netmon on the appropriate servers/client, and reproduce the issue.
a. Click “Create New capture” on the left pane.
b. Click the Play button “>” to begin the capture.
6) Stop Netmon after the issue is reproduced by hitting the stop button.
7) Upload the cap files.
Step 2: Enable Outlook Logging
Enable Outlook Logging Client Side:
For Outlook 2007:
On the Tools menu, click Options.
On the Other tab, click Advanced Options.
Click to select the Enable mail logging (troubleshooting) check box in Outlook 2003 and the Enable logging (troubleshooting) check box in Outlook 2007, and then click OK two times.
For Outlook 2010:
On the File tab, click Options.
In the Outlook Options dialog box, click Advanced.
In the Other section, select the Enable troubleshooting logging(requires restarting Outlook) check box, and then click OK.
Exit and then restart Outlook.s
Step 3: Disable Encryption on outlook
a.Click Start, click Run, type control, and then click OK.
b.Double-click Mail, and then click Show Profiles.
c.Select your profile, and then click Properties.
d.Click E-mail Accounts, select View or Change Existing E-mail Accounts, and then click Next.
e.Select the Exchange account, and then click Change.
f.Click More Settings, and then click the Security tab.
g. Disable the checkbox “Encrypt data between Microsoft Office Outlook and Microsoft Exchange Server check box.”
h.Click OK, click Next, click Finish, and then click Close.
Outlook in Online Mode
Turn Cached Exchange Mode off
1. On the Tools menu, clickAccount Settings.
2. On the E-mail tab, click the Exchange account, and then click Change.
3. Under Microsoft Exchange server, clear the Use Cached Exchange Mode check box.
4. Exit and restart Office Outlook 2007.
Step 5: Add host file entry on outlook client machine to single CAS server
Note: Before you run netmon, please contact an engineer on the support team so netmon on can be started on the cas server. The netmon trace needs to happen simultaneously
Step 6: Gather the ETL Log files & the capture files from Netmon
Note: Outlook generates a new ETL file each time you start Outlook with logging enabled. Therefore, it is important to control the repro scenario so you know which log file(s) to collect from the computer. Please don’t copy all the ETL files in the Temp folder.
The log files are generated in the following format:
OLKRPCLOG_<month>_<day>_<year>_<hour – 24 hr clock>_<minutes>_<seconds>_<index>.etl
For example: OLKRPCLOG_09_06_2008_17_35_47_1.etl
Gather and upload the logs/trace files to Microsoft for analysis