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Random error 500 when using IE

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We have a user base of about 60 people that submit tickets. On random occurences specifically in IE the user will receive an error 500 when trying to access the helpdesk. We have AD authentication pass through enabled so the user clicks a link and they are automatically logged into their dashboard. Has anyone else seen this or have any thoughts on what to look for? I have been through the logs and have not found any concrete evidence of server side errors.

During troubleshooting I have found that clearing the IE cache and reopening IE seems to temporarily fix the issue.

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