We have a website for the NCTech4Good Conference -- http://nctech4good.org. People register on the site to register for conferences, become sponsors, and submit session proposals. We want to be a able to send an occasional email to everyone on the website, currently about 270 users, with conference updates.
We originally used mass_contact module and that worked but I think it sends one message using BCC and understand that is what spammers do and is considered a bad practice, so we are now trying to use views_send with mimemail. We are using Drupal 6.26 and Conference Organizing Distribution (COD) modules.
views_send gives an internal server error, "Premature end of script headers: index.php, referer: http://nctech4good.org/send-mail"
At admin/settings/views_send, I have cron throttle set to 10 (send 10 messages per cron run) -- cron runs every 5 minutes -- and I checked "Log emails" so I can watch message delivery. The script failed after about 190. So I went back to the list of all the addresses and unchecked them all. Then I manually checked each of the remaining 86 and sent the message to them. This time I did NOT get an internal server error and got a normal completion message saying:
86 processed in about 14829 ms.
What so you suggest? Should I go back to mass_contact? It there a php time limit for scripts that should be extended? Should I try to create groups, perhaps using roles, so I can put about 150 in a group and send to one group at a time?

Comments
Execllent
This is a great post and I look forward to the discussion!!
A tangential response
I'm spending an increasing amount of time dealing with SMTP issues; blacklisted servers, missing DKIM/SPF keys, straight-to-spam flagging (or outright rejection) and clients who use their mailbox for mass distribution. In a sending of 1000 mails, it takes one disgruntled recipient to add your name to a blacklist and then the trouble really starts where you don't need it.
MailChimp has excellent integration with Drupal 6.x. I'm not clear if it integrates and synchronizes with the user's table but you can expose a form per list for signup. I'm a fan for letting services like MailChimp deal with all the darkness of mass mail distribution and ensuring your SMTP account doesn't get a black eye. Additionally, when you let php-mail handle mass distribution of mail, you'll miss important feedback: bad email addresses, who's reading your mail, who wants to opt-out, etc.
Kyle
mailto:
On campus we use Outlook and the MS Exchange Server to handle bulk email.
The D7 uses Views and Views PHP in the Displays-Views-Header-Global: PHP to create the mailto: string with a form type button to send it.
Help with site building
Is anyone available for a few hours this week to help me with a couple of site building questions. I am new to Drupal and am having a hard time. Thank you.
Greetings Donnaador
Welcome to the Drupal NC Community. We have a wonderful mix of talent and experience. A couple of hours time is difficult to schedule, but feel free to ask away. Also check out the #drupal-nc IRC channel, a live resource for when you need immediate help. We also have co-working days on the last Friday of every month. It's a great way to work along side other Drupal freelancers at a great coworking location.
Barbara, any interest in holding an "out-of-sequence" coworking Friday at the end of this week, Feb 8?
Kyle
Thank you for the warm
Thank you for the warm welcome!
If an "out-of-sequence" co-working Friday could not be scheduled until the end of the month, would anyone be able/willing to have a "joinme" sesson and I could share my screen and provide some direction in that manner?
I tried to access the #drupal-nc IRC channel without any success. It never opens on my Windows PC (may be blocked at work) and receive a message: mac os x does not recognize internet addresses starting with “irc” on my Mac.
I have lots of questions and not many answers :).