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Nebulous IIS error: 500 Internal Server Error

One of our customers is having this error appear periodically on his client browsers (chrome, firefox and ie) but can clear it by a simple page refresh (undesirable workaround)

This may be a simple bottleneck of system resources starting with RAM but before I go down that road, I want to see if anyone has any better ideas as to a) what is the real problem and b) can it be managed within the current resource constraints?

The server is a 64 bit Windows Server 2008 R2 running in a HyperV env with 32G RAM allocated.  The main application is SQL Server 2008 R2 which is taking 90+% RAM.

We have VB ASP code interfacing between IIS and the SQL server that calling into a DLL to build a graphic chart for display.  The server log error thrown looks like it is coming from our ASP2DLL code which may be from having to cache in that code periodically, given the SQL Server is hogging the memory.  We are experimenting with limiting the RAM that SQL Server will consume which *should* leave more RAM for other system applications to not need to be cached.

We have not been able to reproduce this problem but our customer is seeing in periodically on several clients.  This is a server error, not a client one.

I am attaching a file with datapoints from the server to help with understanding the env and error messages.
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2 Solutions
Dave BaldwinFixer of ProblemsCommented:
Why is 'mmc.exe' using 680 megabytes?  That seems like a lot to me even if it is supposed to be running.
Steven CarnahanNetwork ManagerCommented:
High memory is normal for SQL (it's a real hog) however it only becomes an issue if there are other problems at the same time like a high page/sec memory counter.
FDC2005Author Commented:
I do not know why mmc.exe (Microsoft Management Console) is taking so much RAM.  The server was last reset in early August.  We are requesting a subsequent server reboot to see whether that will clear the main issue as well as reduce RAM for mmc.exe.
FDC2005Author Commented:
Regarding pony10us' comment, since we cannot reproduice this nor have we been logged in during the times when this sporatically hac occured, we don't have a snapshot of the system behavior... which brings up a good point for me to follow up with.  
I will enable the performance logging and see if we can correlate the errors in the logs with monitor points.
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