We have JIRA installed as a local installation and are trying to make JIRA accessible for users in the field without having to use VPN. For this, we have added an alias in the Proxy server which gets rewritten to the internal URL.
When user tried to add an attachment using the external alias, the maximum size so far seen is 100KB. We ran a wireshark trace to trace the traffic and see if the issue is with the network. Nothing related to network was seen in the trace.
However, an HTTP500 was recorded with the error message "An error occurred while attaching file: Read timed out". I am not able to find anything corresponding in the jira or tomcat logs. Any suggestions on which log I should be looking at?
Maybe the problem is the JIRA base URL not set correctly? You must ensure that the base URL is the same as the one you are accessing through the browser, even using a external URL.
If the problem persist, I suggest to open a ticket in support.atlassian.com so we can investigate this behavior.
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