WordPress on IIS 6.0, Windows 2003 – Some Tweaks (URL Rewrite and SMTP)

OK so I lied. Everything wasn’t working after I set up my WordPress blog on IIS 6.0 on Windows 2003. Two things were broke: SMTP (email from the blog) and URL Rewrites/Permalinks.

SMTP worked through IIS just fine, I could telnet and send email out, but from WordPress, it was getting a 501 error. From what I could tell, it was the way that WordPress was formatting the outgoing “mail from” with <From Name>from@address.com . IIS was bombing on the <> in the string (I am pretty sure). I tried some tweaking on WordPress, some plugins for SMTP, couldn’t get them to work. I tried MailEnable, I couldn’t get that to work either. I did fine hMailServer and that does work after configuring it. Like IIS, I have it just set to local, and port 25 is blocked anyway so outside relays won’t work.

The other thing that wasn’t working was my permalinks. By default WordPress doesn’t use permalinks with a rewrite, it just uses ?p=<post id>, but I have mine changed to year/month/day/title. In Linux/Apache, there is mod_rewrite for rewriting URLs, but in IIS 6.0 there isn’t anything (IIS 7 has more functionality). I could have gotten a rewrite DLL and wrote rules, but I found a sweet plugin that does it for me, especially for WordPress permalinks – http://www.binaryfortress.com/wordpress-url-rewrite/

Other than that, everything seems to be working fine. On other news, I have been looking into other blogging engines, comparing/contrasting, etc. Not sure where I will go with that though.



  • webcr8tr

    Can you explain in detail how you got it to work?