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We are using Elmah to handle our errors, and on some of our servers it is working beautifully but on others it is logging and processing the error but not sending the e-mail. I imagine Elmah is hitting some sort of problem sending the mail but I have no way to see what this problem is.
How can I catch and report (even if just logging to the console or a file) errors Elmah itself hits?
Checkout source, build from there, attach dll`s to Your application, start application in webdev, attach studio that has elmah project opened to webdev, re-produce error and see exactly what’s happening.
But in Your case, I would double check if network settings are ok. Seems to me that smtp ports are closed or something. Create small console app that sends e-mails and try to run it on server or use telnet.