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Outlook/Gmail Group Mail Blocked Issue


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#1 sere83

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Posted 11 February 2017 - 01:41 PM

Hi there,

 

I am having an issue with sending an email to a group of 44 contacts in outlook 2016. At the moment outlook is set up to handle 2 email accounts, a yahoo mail and a gmail account.

 

When I attempt to send a simple group email in the gmail account, all the emails fail to deliver and you I get an error message from each saying they were blocked. I have also manually exported a CSV of outlook contacts and imported it into the gmail account online and even created a group for these 44 contacts in the hope this would help.

 

Its has made not difference.

 

Anyone know how i can solve this issue and use outlook to send a group email to 44 contacts?

 

Any help much appreciated thanks.

 

Thanks


Edited by hamluis, 19 February 2017 - 08:10 PM.
Moved from Business Apps to Web Browsing/Email - Hamluis.


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#2 britechguy

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Posted 11 February 2017 - 01:49 PM

If you have the Gmail account set up to sync then your contacts should be available via the Gmail web interface.  I would at least try to send a message to the same group of contacts via Gmail's web interface just to see whether or not you get the same bounce back via that avenue.

 

There are a lot of e-mail servers that have gotten very restrictive about the maximum number of recipients they will accept on a message as a spam prevention technique.  I have, on more than one occasion, had to take the approach of sending the same message to say, 8 addresses at a time, cyclically, until all the addresses I needed to get a message to had been covered.

 

This may, or may not, be related to Outlook or Gmail.  I would not be shocked in any way if every recipients' e-mail servers are spam-trapping based on having 44 simultaneous recipients.  Things have gotten much more restrictive over the last several years.


Brian  AKA  Bri the Tech Guy (website in my user profile) - Windows 10 Home, 64-Bit, Version 1803, Build 17134 

     . . . the presumption of innocence, while essential in the legal realm, does not mean the elimination of common sense outside it.  The willing suspension of disbelief has its limits, or should.

    ~ Ruth Marcus,  November 10, 2017, in Washington Post article, Bannon is right: It’s no coincidence The Post broke the Moore story


 

 

 

              

 


#3 sere83

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Posted 11 February 2017 - 02:23 PM

If you have the Gmail account set up to sync then your contacts should be available via the Gmail web interface.  I would at least try to send a message to the same group of contacts via Gmail's web interface just to see whether or not you get the same bounce back via that avenue.

 

There are a lot of e-mail servers that have gotten very restrictive about the maximum number of recipients they will accept on a message as a spam prevention technique.  I have, on more than one occasion, had to take the approach of sending the same message to say, 8 addresses at a time, cyclically, until all the addresses I needed to get a message to had been covered.

 

This may, or may not, be related to Outlook or Gmail.  I would not be shocked in any way if every recipients' e-mail servers are spam-trapping based on having 44 simultaneous recipients.  Things have gotten much more restrictive over the last several years.

 

Thanks for your help. It is odd because from the yahoo account messages to the group always goes through fine, seems very restrictive to not allow 44 odd emails. Yes i can try from the gmail web interface as i say i have already recreated the group in there manually. If they do manage to send from there what would that suggest the issue is?



#4 britechguy

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Posted 11 February 2017 - 06:43 PM

I honestly can't tell you what that would suggest about the issue other than that you would know it's not at the level of Gmail's servers when they are not interacting with Outlook.

 

If you can send messages from your yahoo account to the same 44 addresses on a single message it's highly unlikely that the issue is on the recipients' ends.

 

Something weird is going on here, but it's a matter of figuring out exactly where in the process the "here" is between Outlook and Gmail.

 

By any chance are you using different access protocols?  Is one account using IMAP and the other POP?


Brian  AKA  Bri the Tech Guy (website in my user profile) - Windows 10 Home, 64-Bit, Version 1803, Build 17134 

     . . . the presumption of innocence, while essential in the legal realm, does not mean the elimination of common sense outside it.  The willing suspension of disbelief has its limits, or should.

    ~ Ruth Marcus,  November 10, 2017, in Washington Post article, Bannon is right: It’s no coincidence The Post broke the Moore story


 

 

 

              

 


#5 sere83

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Posted 12 February 2017 - 01:47 PM

I honestly can't tell you what that would suggest about the issue other than that you would know it's not at the level of Gmail's servers when they are not interacting with Outlook.

 

If you can send messages from your yahoo account to the same 44 addresses on a single message it's highly unlikely that the issue is on the recipients' ends.

 

Something weird is going on here, but it's a matter of figuring out exactly where in the process the "here" is between Outlook and Gmail.

 

By any chance are you using different access protocols?  Is one account using IMAP and the other POP?

 

Hmm i'm actually helping someone out so cant check right now but I think they are both IMAP accounts as I recall. I will double check and maybe try and send a message from the online gmail client. Could it be the antivirus? They are using avast.



#6 sere83

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Posted 15 February 2017 - 04:23 PM

Hey, so I tried sending an email through gmail in chrome and all was well. What could this mean? Would suggest it is an outlook problem or maybe antivirus? What do you think?



#7 britechguy

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Posted 15 February 2017 - 06:26 PM

What I think is that you need to start looking at what, as far as Gmail, is different in how Outlook is accessing it (servers, ports, passwords, etc.) as opposed to how it's working when you're logged in to the native Gmail webmail interface.

 

This is almost certain to be the result of something really trivial, but what that might be is a very open question.  I doubt very much that your antivirus issue or even an Outlook issue, per se.

 

It would be very helpful to have additional information on what, precisely, is coming back in the bounce messages.  Are you able to send to a single one of the e-mail addresses in question when you're just writing to them when using Outlook and the gmail account?


Edited by britechguy, 15 February 2017 - 06:38 PM.

Brian  AKA  Bri the Tech Guy (website in my user profile) - Windows 10 Home, 64-Bit, Version 1803, Build 17134 

     . . . the presumption of innocence, while essential in the legal realm, does not mean the elimination of common sense outside it.  The willing suspension of disbelief has its limits, or should.

    ~ Ruth Marcus,  November 10, 2017, in Washington Post article, Bannon is right: It’s no coincidence The Post broke the Moore story


 

 

 

              

 


#8 sere83

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Posted 19 February 2017 - 07:26 AM

What I think is that you need to start looking at what, as far as Gmail, is different in how Outlook is accessing it (servers, ports, passwords, etc.) as opposed to how it's working when you're logged in to the native Gmail webmail interface.

 

This is almost certain to be the result of something really trivial, but what that might be is a very open question.  I doubt very much that your antivirus issue or even an Outlook issue, per se.

 

It would be very helpful to have additional information on what, precisely, is coming back in the bounce messages.  Are you able to send to a single one of the e-mail addresses in question when you're just writing to them when using Outlook and the gmail account?

 

The gmail account was just automatically set up in outlook, all that was entered was the gmail address and password. Each message gives an auto response saying that that email address has blocked my message. See below link for a screen grab. Yes sending a single message works fine from both gmail web mail and outlook. Also sending the group message to all the recipients in webmail works fine as mentioned.

 

http://i136.photobucket.com/albums/q177/sere84/Screenshot_30_zpsvjy7ky6c.jpg~original


Edited by sere83, 19 February 2017 - 07:38 AM.


#9 sflatechguy

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Posted 19 February 2017 - 08:57 AM

It would help if you could post the wording of the non-delivery receipt (NDR) you are getting when you try to send these emails, as that could help pinpoint where the blockage is occurring.



#10 sere83

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Posted 19 February 2017 - 09:00 AM

It would help if you could post the wording of the non-delivery receipt (NDR) you are getting when you try to send these emails, as that could help pinpoint where the blockage is occurring.

 

no probs, is that not what I posted in the link above though? What happens is I send to a group of 44 and then i get 44 of the above NDS emails in response, each one from a different recipient.



#11 sflatechguy

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Posted 19 February 2017 - 09:12 AM

My apologies. I see it now.

 

It's definitely Google that's blocking it, but the error message isn't very helpful. Did you create the email group in Outlook, or is it a Gmail contact group? If you created the group in your personal contacts in Outlook, it's possible Google is blocking it because it thinks you are trying to send spam.

 

Also, the contents of the email may be a problem. Some spam filters are known to block emails that contain certain words, phrases or URLs.



#12 sere83

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Posted 19 February 2017 - 01:44 PM

My apologies. I see it now.

 

It's definitely Google that's blocking it, but the error message isn't very helpful. Did you create the email group in Outlook, or is it a Gmail contact group? If you created the group in your personal contacts in Outlook, it's possible Google is blocking it because it thinks you are trying to send spam.

 

Also, the contents of the email may be a problem. Some spam filters are known to block emails that contain certain words, phrases or URLs.

 

Yes the email group was created in outlook personal contacts. But then I exported all outlook contacts as a CSV from outlook and imported them into gmail webmail. I the slightly edited the gmail group though after import because the formatting was off though but it is the same addresses. The contents of the email is nothing crazy, just some text about current affairs no url's or phrases that could trigger spam filters from what I see.



#13 sflatechguy

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Posted 19 February 2017 - 01:52 PM

You mentioned the formatting was off after the import. It's possible there are still issues with the character or formatting that is creating problems when trying to send to the group.
If you send individual emails to those addresses, and manually enter the email address, do they still bounce back as undeliverable?

#14 sere83

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Posted 19 February 2017 - 02:20 PM

Hmm well the formatting only seemed off on the gmail webmail CSV import from Outlook, so i changed the contact formatting of the group in gmail webmail and then obviously sent the email to the group through that and none of them bounced back, well 2 did but because the emails were no longer in use not because of blocking.

 

It is worth noting though that Outlook also handles a btyahoo account that has no problems sending messages to the same contact group, which suggests the formatting is ok. It is only when the group mail is sent using gmail in outlook that it causes the issues.


Edited by sere83, 19 February 2017 - 02:21 PM.


#15 sflatechguy

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Posted 20 February 2017 - 01:03 PM

I suspect that's because when you use the group you created in your Outlook, Gmail thinks you are sending spam due to the large number of recipients the email is being sent to. Using a Gmail contact group seems to be your only option here.






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