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limit on BCC recipients
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does anyone know how many recipients I can have in the BCC (blind carbon copy) section of an email message?  I will be sending out some mail soon that will have to have more than 50.  Is that over the limit?  and will the message not be delivered if I boost the count to that many?
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I've been sending a daily distro with zero problems to 96 emails BCC'd. Yesterday and today, I am getting notifications EVERY email address BLOCKED the send. Any assistance would be lovely..
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    you cant use gmail.com addresses  for bulk mail anymore
 
  comment from a Google Employee >> https://productforums.google.com/d/msg/gmail/uH2hN6S5OyM/lzdteH-ifvYJ

  if the Failure Notification includes the text "See https://support.google.com/mail/answer/69585 for more information." then the information below will apply to you.  If not, please disregard the rest of this post and provide the complete error message.   The issue   Gmail engineers have recently (early July 2015, it appears) fixed a bug in an anti-Spam feature of Gmail.  This fix means that regular sending of messages to multiple recipients will result in blocking of the messages to one or more of the recipients if one or more recipients have previously reported a message from you as Spam.  The key elements are regular, multiple and Spam reports.  I don't know if only one Spam report will trigger this or if it takes a few.  I don't know if the Spam report has to be from one of the recipients for this particular message or if just any Spam report against you reduces your reputation.  Receiving bounce reports from non-existent or disabled email accounts will reduce your reputation.   The rules are not exact and Google has not published them (for the express purpose of not allowing real Spammers to work around them) so I cannot give any precise guidelines on how to stay clear of this restriction and in some cases, they appear to be extremely tight.  These rules have existed in Gmail for much longer, but due to the bug, they have not been enforced.   If the bounce message includes the text: Delivery to the following recipient failed permanently:       [email address]   Technical details of permanent failure: Message rejected.  See https://support.google.com/mail/answer/69585 for more information. then you have been affected by this restriction.  The key here is the reference to the Help Article 69585.  If you receive any other bounce message then please disregard this information.  If your normal usage triggers this rule, there is nothing you can do to bypass it, you must change to a solution that supports regular bulk messaging.  If you send, for example, weekly messages to hundreds of users, then you will never get reliable delivery using Gmail directly.


  Solutions  
 
( note if you use a signature that may be the cause ) 
 
 
Note that some recipients use "Report as Spam" as an easy way to stop seeing your messages, so including instructions clearly visible in your messages (preferably at the beginning, so that recipients see this before reading anything) on how to get taken off the list is a good way to avoid being caught by the restriction, although if you have discovered this topic, then that advice is probably too late.  Google has recently added a feature to Gmail that offers users the choice to mute this type of conversation instead of mark it as Spam in order to reduce false use of the Spam marker.Always and immediately remove people who have asked to be removed as well as email addresses that fail.

  GMass -   no change of email address The simplest solution appears to be to use the Chrome browser with the extension GMass ( https://chrome.google.com/webstore/detail/gmass-10/ehomdgjhgmbidokdgicgmdiedadncbgf?utm_source=gmail).
 
 This allows you to send customised bulk messages, but even without the customisation, it will send your message individually to each of the recipients in the To field bypassing the check on messages to groups.
 
 This is incredibly easy to set up - just install, then drop your group into the To field of a message and use the GMass Send button that will appear right next to Gmail's send button. NB: (a) GMass will not bypass Gmail's total message restriction of 500 recipients per 24 hours.   (b) GMass will create an individual sent message in your Sent folder for each recipient.   (c) Recipients will not be able to Reply All as the message they receive will look like a personal message addressed to them only
 
  MailChimp (or other bulk mailing systems) - Free - no change of email address The next solution is to use a bulk mailer such as MailChimp.  This is free for use in the volumes that Gmail was previously able to handle and is relatively easy to set up according to reports.  Significantly, MailChimp messages provide an embedded method to unsubscribe. This not only leads recipients to not use Report as Spam, but also relaxes the rules on Spam detection.  
 
Google Groups - Free - no change of email address A third solution which is excellent for large "fixed" groups is to use Google Groups.  Please note that Google Groups are different from Gmail's contact groups and are created at groups.google.com.  These are a little painful to set up as you can only load members ten at a time by copying and pasting from your address list, however the functional flexibility is huge.  Messages sent from Google Groups also provide an embedded method to unsubscribe.  
 
 
Google Apps for Work - Free for registered non-profits - requires change of email address The final solution is to create a Google Apps for Work account.  This is only appropriate for organisation who have an available domain name or can get one.  This solution is not free like the others, but if your organisation is a registered non-profit, then in most countries, the only cost is registering the domain name.  A domain name based Gmail account is not subject to the regular bulk mail tests since the sender is more readily traced. For more information about this type of account, please see apps.google.com.  
 
 
Do these work? There are testimonials from Gmail users who have tried all of these solutions in an old topic at https://productforums.google.com/forum/#!topic/gmail/uH2hN6S5OyM.  To find them, use the keyboard shortcut "o" to open (expand) all the posts then use your browsers word search (usually CTRL f) to find "GMass", "MailChimp", "Apps for Work" or "Google Groups".  Not all posts include the exact term, so some intuition might be needed.   Here is a short list of links that will take you to the exact post (if you wait long enough):
 
 
 
 
 
 
Assistance with setting up solutions  
 
For assistance with setting up Google Groups or an Apps for Work account, use the Apps Help Centre Google Apps Help Articles Google Apps Product Forum
 
  For assistance with setting up Gmass (although you won't need any) and MailChimp, contact the support sites for those products: https://www.gmass.co http://kb.mailchimp.com
 
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