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Bounced email

Avatar Mark Ford
Periodically I send out a BCC email to a group of about 48 people and all except one gets through. This has happened 3 or 4 times over the last two months [so is unrelated to Lion!].

This is part of the message I get about the bounced one:
To: Undisclosed-recipients: &lt;&gt;; Reason: SMTP transmission failure has occurred<br />
Diagnostic code: smtp;550-Syntax error in the headers: Rejected after DATA: missing or malformed local part: failing address in &quot;To:&quot; header is: Undisclosed-recipients: &lt;&gt;; If you are using BCC make sure you have an address in the TO field try putting your own address in t

The message ends with the stray letter t.

I am using BCC and there are 48 addresses in the TO field.

Curious.

The card in Address Book seem to be set up properly.
If I then send the email to just that person it is sent OK.

Anone have any idea what is going on?

Re: Bounced email

Avatar Derek Wright
I presume you are using groups to gather the recipients together, have you tried splitting the recipients into two groups and then sending the two groups out separately.

Do you keep a copy of the file of the email and include yourself on the copy list - if so can you see an error in the email addressees when you do a View - Message - All Headers.

If these are OK - does your ISP have an anti spamming process that limits the number of addressees in a single transmission, of an email

Re: Bounced email

Avatar Mick Burrell
Mark - could you clarify. You say there are 48 addresses in the TO field - what are you putting in the BCC field? I think that if you are using an Address Book group (of 48) that although you enter the group name in the TO field, Mail expands the addresses and puts them in the BCC field.

Mail will allow you to send email with nothing in the TO field as long as there's at least one address in either of the other two fields. Some (all?) Windows software needs an address in the TO field which is why Windows people who know what BCC is for (!) put their own address in the TO field. It sounds to me as if the email server of one recipient is also struggling because there's no address in the TO field. (The stray t is probably has a missing i i.e. it.)

If this turns out to be the case, to get round it you'll have to put the group name and your own address in the TO field. I'd put your address first and then the group in case it sees "undisclosed recipients" (which Mail may or may not put if your address is there) and throws its toys out of the pram again.

Re: Bounced email

Avatar Mark Ford
Thank you for you for your replies - unfortunately I can't irritate the group by sending test mail but next time I will try putting myself into the TO field followed by the name of the Smart Group and see how that goes.

Re: Bounced email

Avatar Drew McFarlane
Hi Mark, was this issue ever resolved?

Re: Bounced email

Avatar Mark Ford
Hi Andrew, I am afraid I have forgotten! I have only sent out 2 batches since then & I sent the odd one separately. However I have to send out a batch over the weekend so i will try sending to all and will report back on how it goes.
 
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