Different Jpegs with same name returning the first retrieved in IIS

Ciaran Flanagan 1

Hi All,

Im Migrating a Images server from a 2008 R2 to a 2019 server. It all seems to be working except for one odd thing that I cant figure out how to resolve. For reasons of the legacy system this feeds images to I cant rename files etc to be unique.

Say I have two virtual folders
/logos/focusedlogo/logo1.jpg
/logos/unfocusedlogos/logo1.jpg

On the 2008 server (IIS7) I browse to http://url/logos/focusedlogo/logo1.jpg and I get the correct file, if I do the same for http://url/logos/unfocusedlogos/logo1.jpg I get that file. On a browser I can switch between these and always the correct file is displayed.

However, On the 2019 server (IIS10) If I browser to http://url/logos/focusedlogo/logo1.jpg I get the correct image but if I browse to http://url/logos/unfocusedlogos/logo1.jpg I get the same images as the first time again. This is reversible, The one I browse first I keep getting that same image returned to me.

These no specific caching configurations setup on the 2008 server and all settings I can find are mirrored on the two servers.

Any idea how to resolve?

Lex Li (Microsoft) 4,662 Reputation points Microsoft Employee

2021-06-21T14:11:39.46+00:00

Enable FRT on both machines so that you can learn how the response messages are generated https://learn.microsoft.com/en-us/iis/troubleshoot/using-failed-request-tracing/troubleshooting-failed-requests-using-tracing-in-iis Then the culprit should be revealed.
Ciaran Flanagan 1 Reputation point

2021-06-21T14:40:17.503+00:00

Thanks for the suggestion but unfortunately there isn't any failure or failure message. the request appears to work fine but its not the correct jpeg file returned.
Sam Wu-MSFT 7,036 Reputation points Microsoft Vendor

2021-06-22T03:24:11.027+00:00

@Ciaran Flanagan You can try to clear the browser cache and reset iis, then try again to see if the same problem.
Lex Li (Microsoft) 4,662 Reputation points Microsoft Employee

2021-06-22T05:31:07.48+00:00

You can trace all HTTP responses (not only errors) with FRT if you set response codes to 200-999. You can see a lot more than "the request appears to work", because all technical details are there.
Ciaran Flanagan 1 Reputation point

2021-06-22T08:56:01.843+00:00

I've reset browser cache and reset iis a number of times. always the same result. when i do the same on the old win 2008 server it doesn't have this problem at all.
Sam Wu-MSFT 7,036 Reputation points Microsoft Vendor

2021-06-23T08:49:25.32+00:00

@Ciaran Flanagan Have you tried another browser? or there are some special settings in iiis, such as url rewrite.