URL Rewrite in IIS 8.5 HTTPS to HTTPS end in gateway eroor

Question

I really could use some help from the experts out there...

Currently we use a reverse proxy to publish several http sites to the outside world, all are running fine.

Now I need to give HTTPS access to an internal HTPPS site.

• internal HTTPS site (https://tobadata.internal.lan) is accessible from the reverse proxyserver running iis 8.5 and urlrewrite 3.0, all certifcates are OK, no errors
• certificate for the external url (ess.outside.be) is installed on the rproxy server

• certificate is bound to the specific webserver running on the rproxy server.

  I have copied the simple basic rule I normally use for my HTTP sites

   <rewrite>
       <rules>
           <rule name="ReverseProxyInboundRule1" enabled="true" patternSyntax="Wildcard" stopProcessing="true">
               <match url="*" />
               <conditions>
                   <add input="{HTTPS}" pattern="On" />
               </conditions>
               <action type="Rewrite" url="https://tobadata.internal.lan/{R:0}" />
           </rule>
       </rules>
   </rewrite>
  

  When using this setup, I'm getting an error "502 - Webserver received an invalid response while acting as a gateway or proxy server"

  I have enabled failed request tracing, capturing 502 errors, but this isn't helping me, since it seems that the rewrite rule works as expected?

  1. GENERAL_REQUEST_START SiteId="2", AppPoolId="ess", ConnId="1610612741", RawConnId="0", RequestURL="https://ess.outside.be:443/", RequestVerb="GET" 14:36:04.272
  2. GENERAL_ENDPOINT_INFORMATION RemoteAddress="77.109.122.130", RemotePort="53751", LocalAddress="192.168.1.80", LocalPort="443" 14:36:04.288
  3. GENERAL_REQUEST_HEADERS Headers="Connection: Keep-Alive Accept: text/html, application/xhtml+xml, image/jxr, / Accept-Encoding: gzip, deflate Accept-Language: nl-BE Host: ess.outside.be User-Agent: Mozilla/5.0 (Windows NT 10.0; WOW64; Trident/7.0; rv:11.0) like Gecko " 14:36:04.288
  4. GENERAL_GET_URL_METADATA PhysicalPath="", AccessPerms="513" 14:36:04.288
  5. HANDLER_CHANGED OldHandlerName="", NewHandlerName="StaticFile", NewHandlerModules="StaticFileModule,DefaultDocumentModule,DirectoryListingModule", NewHandlerScriptProcessor="", NewHandlerType="" 14:36:04.288
  6. URL_REWRITE_START RequestURL="/", Scope="Distributed", Type="Inbound" 14:36:04.288
  7. RULE_EVALUATION_START RuleName="ReverseProxyInboundRule1", RequestURL="", QueryString="", PatternSyntax="Wildcard", StopProcessing="true", RelativePath="/" 14:36:04.288
  8. PATTERN_MATCH Pattern="*", Input="", Negate="false", Matched="true" 14:36:04.288
  9. CONDITIONS_EVALUATION_START LogicalGrouping="MatchAll" 14:36:04.288
  10. CONDITION_EVALUATION Input="{HTTPS}", ExpandedInput="on", MatchType="Pattern", Pattern="On", Negate="false", Succeeded="true" 14:36:04.288
  11. CONDITIONS_EVALUATION_END Succeeded="true" 14:36:04.288
  12. REWRITE_ACTION Substitution="https://tobadata.internal.lan/{R:0}", RewriteURL="https://tobadata.internal.lan/", AppendQueryString="true", LogRewrittenURL="false" 14:36:04.288
  13. RULE_EVALUATION_END RuleName="ReverseProxyInboundRule1", RequestURL="https://tobadata.internal.lan/", QueryString="", StopProcessing="true", Succeeded="true" 14:36:04.288
  14. GENERAL_SET_REQUEST_HEADER HeaderName="X-Original-URL", HeaderValue="/", Replace="true" 14:36:04.288
  15. URL_CHANGED OldUrl="/", NewUrl="https://tobadata.internal.lan/" 14:36:04.288
  16. URL_REWRITE_END RequestURL="https://tobadata.internal.lan/" 14:36:04.288
  17. USER_SET AuthType="", UserName="", SupportsIsInRole="true" 14:36:04.288
  18. HANDLER_CHANGED OldHandlerName="StaticFile", NewHandlerName="ApplicationRequestRoutingHandler", NewHandlerModules="ApplicationRequestRouting", NewHandlerScriptProcessor="", NewHandlerType="" 14:36:04.288
  19. GENERAL_SET_REQUEST_HEADER HeaderName="Max-Forwards", HeaderValue="10", Replace="true" 14:36:04.288
  20. GENERAL_SET_REQUEST_HEADER HeaderName="Host", HeaderValue="tobadata.internal.lan", Replace="true" 14:36:04.288
  21. GENERAL_SET_REQUEST_HEADER HeaderName="X-Forwarded-For", HeaderValue="77.109.122.130:53751", Replace="true" 14:36:04.288
  22. GENERAL_SET_REQUEST_HEADER HeaderName="X-ARR-SSL", HeaderValue="4096|256|C=IL, O=StartCom Ltd., OU=StartCom Certification Authority, CN=StartCom Class 2 IV Server CA|C=BE, S=OV, L=RN, SN=DM, G=T, CN=ess.outside.be", Replace="true" 14:36:04.288
  23. GENERAL_SET_REQUEST_HEADER HeaderName="X-ARR-ClientCert", HeaderValue="", Replace="true" 14:36:04.288
  24. GENERAL_SET_REQUEST_HEADER HeaderName="X-ARR-LOG-ID", HeaderValue="075dbaec-f845-4e32-985d-3761117ba9ad", Replace="true" 14:36:04.288
  25. GENERAL_SET_REQUEST_HEADER HeaderName="Connection", HeaderValue="", Replace="true" 14:36:04.288
  26. URL_CHANGED OldUrl="https://tobadata.internal.lan/", NewUrl="/" 14:36:04.303
  27. GENERAL_SEND_CUSTOM_ERROR HttpStatus="502", HttpSubStatus="3", FileNameOrURL="502.htm" 14:36:05.366
  28. GENERAL_SET_RESPONSE_HEADER HeaderName="Content-Type", HeaderValue="text/html", Replace="true" 14:36:05.381
  29. GENERAL_FLUSH_RESPONSE_START 14:36:05.381
  30. GENERAL_RESPONSE_HEADERS Headers="Content-Type: text/html Server: Microsoft-IIS/8.5 " 14:36:05.381
  31. GENERAL_RESPONSE_ENTITY_BUFFER Buffer=" 502 - Web server received an invalid response while acting as a gateway or proxy server. header{width:96%;margin:0 0 0 0;padding:6px 2% 6px 2%;font-family:"trebuchet MS", Verdana, sans-serif;color:#FFF;

  background-color:#555555;}

  content{margin:0 0 0 2%;position:relative;}

  .content-container{background:#FFF;width:96%;margin-top:8px;padding:10px;position:relative;} -->

  Server Error

  502 - Web server received an invalid response while acting as a gateway or proxy server.

  There is a problem with the page you are looking for, and it cannot be displayed. When the Web server (while acting as a gateway or proxy) contacted the upstream content server, it received an invalid response from the content server.

  " 14:36:05.381

  32. GENERAL_FLUSH_RESPONSE_END BytesSent="1616", ErrorCode="The operation completed successfully. (0x0)" 14:36:05.381
  33. GENERAL_REQUEST_END BytesSent="1616", BytesReceived="266", HttpStatus="502", HttpSubStatus="3" 14:36:05.381