wordpress, php, windows, iis 6 - wp_mail http error 500

I've inherited a wp site on a windows 2003 box with iis6 and php.

All of a sudden, any mail-related function throws an http 500 error and I get no output.

I've traced through the code to find the offending line: wp_mail ( );

If I comment it out, no error.  (No mail, of course, but no error).  Firebug gives me the http 500 error and some other info but nothing points to a culprit.

HELP!!
snowdog_2112Asked:
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snowdog_2112Author Commented:
Update, fwiw.

I reinstalled and did a repair install of PHP on the server.  No difference.  Still getting an HTTP 500 error with anything that calls wp_mail.

I've pointed the SMTP server in WP to an external SMTP server to see if Wireshark would see any packets - nope.

I created a php page in the wp folder that DOES send mail using the php mailer - whatever the stock, default mail command uses.

Thsi tells me it's definitely in WP somewhere.
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Jason C. LevineNo oneCommented:
>> I've pointed the SMTP server in WP to an external SMTP server to see if Wireshark would see any packets - nope.

Hmph.  Can I ask you try it again and this time use the following to configure the email in WordPress?

http://wordpress.org/extend/plugins/configure-smtp/
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snowdog_2112Author Commented:
Hmph?  Are you the author of the plug-in?

I was in no way suggesting the plug-in is not working.  I get the same http 500 on *any* mail operation, including Contact Form 7 (tried 2 different versions of cf7 too).

I do have it set up as shown in the link.  I was saying I've tried many different settings in an attempt to fix it or at least see if I can get more information pointing to the point of failure.

I've tried:
localhost
<ip of server>  <-- SMTP runs on the same server hosting this WP site.
127.0.0.1
<fqdn of server>
all the above, using port 8025  <-- added 8025 to local SMTP server.

Thanks.
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Jason C. LevineNo oneCommented:
>> Are you the author of the plug-in?

Good lord, no :)  I was hoping that you may have misconfigured something and giving you an admin interface to set SMTP settings in WordPress would have resolved that.  It's hard to gauge your skill level from the post.

>>  I get the same http 500 on *any* mail operation, including Contact Form 7 (tried 2 different versions of cf7 too).

Weird.  Which version of WP is running?
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snowdog_2112Author Commented:
wordpress 3.0.1

Can't tell a version on configure-smtp
Contact Form 7 is 2.4.1

Still getting the http 500.

Let me know if there's anything else I can check.

My Skill Level (1 - 10, 10 = savant):
Windows - 8
IIS - 7
SMTP - 5
WP - 2
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snowdog_2112Author Commented:
Still fighting this.  I've wiresharked the $#!+ out of this and can't see anything suggesting issue.

Since I can put a simple php page in the same IIS site and send mail using a php page, I am pretty sure php, iis, and smtp are working, this seems to me to point back to wordpress.

I just don't know enough of wp to know how to replace the wp_mail command with something like the php mail command...
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Jason C. LevineNo oneCommented:
Yeah, I'm not sure how to do it with IIS either.  Can you install WordPress 3.3.2 on a testing domain and see if it will send mail?  It may also be a version specific thing.
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snowdog_2112Author Commented:
Waiting for my customer to authorize more time to spend chasing my tail on this...

Setting up a lab case would be hours of prep, and even if it works, there's not a good mechanism to transfer it to the problem system - i.e., if it works, that still doesn't tell me *why* it doesn't work on the problem machine, nor how to fix it.
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Jason C. LevineNo oneCommented:
if it works, that still doesn't tell me *why* it doesn't work on the problem machine, nor how to fix it.

No, but we can then refer to the changelog and see what they changed and start chasing it down from there.  

Alternately, if it works in 3.3.2 just upgrade WordPress on the production machine and that's the functional end of the issue.  The philosophical ending can be relegated to hobby status.
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snowdog_2112Author Commented:
Sorry guys - the end use on this has not authorized additional resources (i.e., money) for me to fix the issue.  Thanks all for the help, but I still have no answer.  Hopefully we can do a version upgrade soon and fix it that way.

Thanks again.
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snowdog_2112Author Commented:
no solution found.
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