IIS Reverse Proxy Error 500

On-Premise
1

I am trying to setup Sentry behind an IIS that is working as Reverse Proxy

The reverse proxy is setup for incoming and outgoing rules. When I navigate to the url then the following request happsn:

  • call to reverse proxy url 302
  • call to /auth/login/ 302
  • call to /auth/login/sentry/ 500 URL Rewrite Module Error.

What I see is that on this request the Accept-Encoding is gzip, deflat.

I have checked the nginx.conf file and there the line gzip off is set.

What am I doing wrong.

Kind regards,
Michael

2

Without more logs, it is hard to speculate on why. I’m not sure this is related to gzip at all.

3

Which logs do you need? IIS or nginx?

4

Both?

5

ISS tells me 500.52 Outbound rewrite rules cannot be applied when the content of the HTTP response is encoded (“gzip”)
Going into deep when setting the following works: Goto Compression Page and disable “Enable dynamic content compression”
Can this information be added to the readme for other folks?

6

This seems very specific to ISS and not Sentry, otherwise you are more than welcome to improve our docs over at https://develop.sentry.dev/self-hosted/

7

Just FYI,

attachted you will find a working web.config for IIS Reverse Proxy to be fully compatible with Sentry. It took quite a lot of work to find out every strange IIS behavior and fix it to have a fully working Sentry

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <rewrite>
      <outboundRules>
        <rule name="ReverseProxyOutboundRule1" preCondition="ResponseIsHtml1">
          <match filterByTags="A, Form, Img" pattern="^http(s)?://sentry_host:9000/(.*)" />
          <action type="Rewrite" value="http{R:1}://public_host/{R:2}" />
        </rule>
        <preConditions>
          <preCondition name="ResponseIsHtml1">
            <add input="{RESPONSE_CONTENT_TYPE}" pattern="^text/html" />
          </preCondition>
        </preConditions>
      </outboundRules>
      <rules>
        <clear />
        <!-- remove this rule if lets encrypt is not required -->
        <rule name="LetsEncrypt" stopProcessing="true">
          <match url=".well-known/acme-challenge/*" />
          <conditions logicalGrouping="MatchAll" trackAllCaptures="false" />
          <action type="None" />
        </rule>
        <!-- remove this rule if redirecting to https is not required-->
        <rule name="Enforce HTTPS" stopProcessing="true">
          <match url="(.*)" />
          <conditions logicalGrouping="MatchAll" trackAllCaptures="false">
            <add input="{HTTPS}" pattern="^OFF$" />
          </conditions>
          <action type="Redirect" url="https://{HTTP_HOST}/{REQUEST_URI}" />
        </rule>
        <rule name="ReverseProxyInboundRule1" stopProcessing="true">
          <match url="(.*)" />
          <action type="Rewrite" url="http://sentry_host:9000/{R:1}" />
        </rule>
      </rules>
    </rewrite>
    <!-- dynamic compression must be disabled-->
    <urlCompression doStaticCompression="true" doDynamicCompression="false" />
    <security>
      <!-- otherwise the + sign from prefix@version+sha will not work -->
      <requestFiltering allowDoubleEscaping="true" />
    </security>
  </system.webServer>
  <system.web>
    <!-- otherwise the : sign from eventSlug within /organizations/:orgId/performance/:eventSlug/ route will not work -->
    <httpRuntime requestPathInvalidCharacters="*,%,?,\,&amp;,&lt;,&gt;" />
  </system.web>
</configuration>

Note:

  • sentry_host has to be replaced with the IP adress where sentry is running
  • public_host is the host which is used to reach the sentry instance from the internet
8

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