Some Notes on the Machines

A very good reference for 2007:

http://www.msexchange.org/articles-tutorials/exchange-server-2007/management-administration/exchange-2007-message-size-limits.html

And another for both:

http://exchangepedia.com/2007/09/exchange-server-2007-setting-message-size-limits.html

Here is a VBscript which, if edited for your Gmail account and environment, will work well on anything XP, Server 2003, or above. It does not require any additional installations, CDO is an object built in to Windows:

EmailSubject = "Sending Email by CDO"
EmailBody = "This is the body of a message sent via" & vbCRLF & _
		"a CDO.Message object using SMTP authentication."

Const EmailFrom = "self@gmail.com"
Const EmailFromName = "My Very Own Name"
Const EmailTo = "someone@destination.com"
Const SMTPServer = "smtp.gmail.com"
Const SMTPLogon = "self@gmail.com"
Const SMTPPassword = "gMaIlPaSsWoRd"
Const SMTPSSL = True
Const SMTPPort = 465

Const cdoSendUsingPickup = 1 	'Send message using local SMTP service pickup directory.
Const cdoSendUsingPort = 2 	'Send the message using SMTP over TCP/IP networking.

Const cdoAnonymous = 0 	' No authentication
Const cdoBasic = 1 	' BASIC clear text authentication
Const cdoNTLM = 2 	' NTLM, Microsoft proprietary authentication

' First, create the message

Set objMessage = CreateObject("CDO.Message")
objMessage.Subject = EmailSubject
objMessage.From = """" & EmailFromName & """ <" & EmailFrom & ">"
objMessage.To = EmailTo
objMessage.TextBody = EmailBody

' Second, configure the server

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/sendusing") = 2

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/smtpserver") = SMTPServer

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/smtpauthenticate") = cdoBasic

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/sendusername") = SMTPLogon

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/sendpassword") = SMTPPassword

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/smtpserverport") = SMTPPort

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/smtpusessl") = SMTPSSL

objMessage.Configuration.Fields.Item _
("http://schemas.microsoft.com/cdo/configuration/smtpconnectiontimeout") = 60

objMessage.Configuration.Fields.Update

' Now send the message!

objMessage.Send

For many years there was ‘blat’, the all-purpose command-line mailer for Windows.  However, blat was never updated for SSL, and a great many email providers (e.g.,. Gmail) require SSL.  One can add a second tool called ‘stunnel’ to create a chain for the purpose, but I don’t like to kludge that much. 

For a while I preferred the applet ‘email’, which is part of Cygwin. However, this is not a standalone applet, and there have been other issues. Just now SwithMail came to light for me:

http://www.tbare.com/software/swithmail.html

Am testing. So far, it is working very well indeed.

Several certificate issues involving Outlook 2007/2010 and SBS 2008/2011 are covered here:

http://blogs.technet.com/b/sbs/archive/2010/01/05/troubleshooting-certificate-mismatch-warnings-in-outlook-2007-clients-on-small-business-server-2008.aspx

Here is an online tool:

https://www.testexchangeconnectivity.com/

put up by Microsoft, which tests all Exchange server communications, including Outlook Anywhere, mobile/ActiveSync/Android/iPhone, etc.  The downloadable tool at the following web site, seems to work better sometimes:

https://store.accessmylan.com/main/diagnostic-tools

The following two KBs, if their fix-it steps are done in order, will fix many OWA and ActiveSync problems:

1. http://support.microsoft.com/kb/883380
2. http://support.microsoft.com/?id=817379

A large number of things to do in case of many specific error-codes, is here:

http://www.pocketpcfaq.com/faqs/activesync/exchange_errors.php

This:

http://www.zindus.com/

is reportedly the best.

The tool discussed here:

http://support.microsoft.com/kb/287497

which actually appears to be installed with every copy of Outlook, works very well.

Here is a very good summary:

http://www.allspammedup.com/2008/12/using-ip-block-list-providers-and-the-connection-filter-agent-in-exchange-2007/

And if you fit certain qualifications:

http://www.spamhaus.org/organization/dnsblusage.html

it is free of charge.

DigiCert has a number of tools for us:

https://www.digicert.com/util/

The one on that page can fix a certificate chain, and there are others linked at the bottom.

SPF records are DNS entries for entire domains, which do a whole lot to prevent spam.  They are required on the sender side, these days, for email to be successfully received by many carriers small and large, including Yahoo and Embarq and many others.  For lots of general information:

http://www.openspf.org

For more details and syntax:

http://www.openspf.org/SPF_Record_Syntax