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URL Rewrite Throwing 500.50 Error on Reverse Proxy attempt

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I swear I had this working prior to the last round of Windows Updates, but now I can't figure out for the life of me what's going on.

Here's the Rewrite entry in the web.config (names changed):

<rewrite><rules><rule name="Reverse Proxy 1"><match url="^blog(/)?$" /><serverVariables><set name="HTTP_X_CUSTOM_HEADER" value="b99f2a-6ef1-7bba-11de-ff6b1ee377" /></serverVariables><action type="Rewrite" url="http://www.example.com/" /></rule><rule name="Reverse Proxy 2"><match url="^blog(/.*)?$" /><serverVariables><set name="HTTP_X_CUSTOM_HEADER" value="b99f2a-6ef1-7bba-11de-ff6b1ee377" /></serverVariables><action type="Rewrite" url="http://www.example.com/blog{R:1}" /></rule><rule name="Redirect Everything to Wordpress Home"><match url=".*" /><conditions logicalGrouping="MatchAll"><add input="{REQUEST_FILENAME}" matchType="IsFile" negate="true" /><add input="{REQUEST_FILENAME}" matchType="IsDirectory" negate="true" /></conditions><action type="Rewrite" url="index.php" /></rule></rules></rewrite>

Application Request Routing has been enabled with all settings at their defaults. Before I ran updates and restarted the server last week, going to /blog, pulled content from our blog partner without issue. Now, when I go to /blog, I get the following:




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