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Group mailing question

Have to send up a page to allow my administrators to send out a group email. Wondering what the opinions are out there on this question:

Is it better to send out 30 separate emails or to put the whole batch of recipients in as cc: or bcc: in just a single email?

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PHP

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@NogDogMar 02.2017 — If all the recipients are internal and therefore on the same mail system, it's probably simplest to create a group alias on your company's mail system that you could then send one email to, and let it take care of distributing it -- plus you can then manage that list via the mail system's tools instead of in your application code.

If that's not the case or setting up such an alias is otherwise not possible, then certainly one email with a CC list would be more efficient, particularly if just using the built-in PHP mail() function, which is not optimized for mass mailing use -- not that 30 constitutes much of a "mass". ? Using BCC might be a bit problematic if you are concerned about spam filters, as they may tend to look less favorably upon large bcc lists.
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@ginerjmauthorMar 02.2017 — The messages are going out to a variety of domain names. The total quantity is at most 100 and will not be very frequent either. I could do this with PHP Mailer but had thought of doing it with the old mail() function.

Does that help point out a direction?
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@NogDogMar 02.2017 — I'd personally probably still use PHPMailer, just because it's better than I am at doing any/all fiddly stuff regarding headers and such, including attachments, HTML formatting, whatever. ?

If sending out 100 emails to assorted addresses, I might be inclined to put any new message into some DB table or somewhere in a file, then have a cron job call my PHP (or whatever) script to actually send the mails (then mark it as completed so it doesn't try to send it again). In that case, you could set up everything in one PHPMailer object, then just loop through your list of email addresses/names, change the "To:" header, and send() each one off. (IIRC, you need to make sure you clear the send-to address before adding a new one -- but it's been awhile, so I may be wrong.)
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@ginerjmauthorMar 02.2017 — So now you're of the opinion that I should send the emails one at a time? Why a cron? Why not have it triggered from a form where the boss types out his message and hits Send Mails?
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@NogDogMar 02.2017 — I'm not dead-set on one at a time vs. all at once vs. groups of N addresses at a time. That might be more a business decision as to whether you want every recipient to know who else received it or not. If you decide one message to rule them all is fine, then the cron approach is likely overkill; but if 100 separate messages, I was just envisioning that might take enough time that it might be better as a background job of sorts. Of course, you could just try it from your web form handler, and decide it's fine that way -- or if it takes too long, at that point decide to move it to it's own background job. The "agile" way would be to take whatever you think is "good enough", try it out, and if the stake-holders are happy with it, you're done. If not, then it's re-factoring time. ?
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@ginerjmauthorMar 02.2017 — I was actually more concerned about the response time and/or the resource usage as well as any "mail server" issues with an email going out to 50-100 people all at once.
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@NogDogMar 03.2017 — I [I][B]think[/B][/I] that if you did it as one send to all the addresses at once, PHP would hand it off to the mail server and be done with it, and your PHP script would consider it complete and move on. The mail server would then be doing its own thing to send a copy to each recipient, but your script would not wait for it -- nor would it know if they all really got sent or not. (You'd probably have to check the mail server logs for that.)
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@ginerjmauthorMar 03.2017 — Do most mail servers react more to a big block of individual emails coming thru or to a single email going to a lot of recipients? I don't want my (host's) mail server to be flagged because of my activity. Or should I ask my host?
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@NogDogMar 03.2017 — I'll have to defer that to more knowledgeable people than me. I don't know if one email with X recipients counts as X emails in terms of any limits your hosting service may have, etc. I do know that most businesses that do a lot of emailing (for an unknown value of "a lot") will either use a 3rd-party service with their own servers and who work to keep their IPs off of spam lists, or else they set up their own mail server/IP; but yeah, checking with whoever is currently hosting your site regarding email usage/limits would be a good start.
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@ginerjmauthorMar 03.2017 — Thanks Nogdog. I know more than I did a couple days ago. Will pursue with my hoster.
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