When troubleshooting the arcgisoutput virtual directories you can try a couple of things: If an image is actually getting generated and placed in the arcgisoutput folder, try viewing it directly in your browser using the URL configured for that virtual directory. eg: http://<servername>/arcgisoutput/_ags_map54112cdc0d734f2b8dcfeeeb2e78405b.png *note: arcgisouput images will only be generated for non-cached services This will test your virtual directory configuration and make sure IIS is working properly. The next step (assuming you don't find a problem with IIS) will be to use something like fiddler (http://www.fiddler2.com/fiddler2/version.asp) to watch the connections that ArcMap attempts when trying to access the arcgisoutput folder. Start fiddler, then start ArcMap and watch the conversation in fiddler as ArcMap attempts to load the images from the arcgisoutput folder. Using fiddler, you can diagnose the http connection to IIS that is failing by copying each failed URL into your browser and working to diagnose the problems it reports. Hope these tips helped! -William
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