Unable to upload large attachment even when attachment file size limit exceeds it

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Users receives a "Internal Error" message when uploading large attachments even though the attachment size limit had been set appropriately in JIRA. Although the upload failed, there is no useful information or error that can be found inside the logs.


Generate a HAR file on the user side while replicating the issue. Search for the POST entry related to the file attachment. The POST data is incomplete and the server response code is "0".

The logs and HAR file also indicates that JIRA instance is configured behind a proxy. A simple telnet test to the JIRA instance hostname reveals that the JIRA instance is behind Microsoft IIS webserver.

HTTP/1.1 400 Bad Request
Content-Type: text/html; charset=us-ascii
Server: Microsoft-HTTPAPI/2.0
Date: Wed, 09 Mar 2016 06:18:44 GMT
Connection: close
Content-Length: 326


Microsoft IIS webserver "maxAllowedContentLength" is set below JIRA's attachment size limit.


Change the "maxAllowedContentLength" in web.config to match or exceed JIRA's attachment size limit. For example:

        <requestLimits maxAllowedContentLength="10000000" />
Last modified on Mar 9, 2016

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