Having issues sending emails with our Outlook account through a CRM (customer resource manager).

Jenn - Becca JBRealtors 1

I am trying to send emails through the Jarjamedia.com system. I have our email account set up and am trying to send a mass email to about 60 people. None of the people received them that I'm aware of and there was nothing in my sent folder in the Outlook app. I tried sending another one and it went to 9 people, all the others came back undeliverable. One client emailed back and when I tried responding, I received an error ('Tricia Clark' on 12/14/2020 6:28 PM This message could not be sent. The client operation failed. Try sending the message again later, or contact your network administrator). I had another email doing the same. I spoke to Jarja's customer support and they are saying that it's on the Outlook's side.

Kael Yao-MSFT 37,496 Reputation points Microsoft Vendor

2020-12-16T02:00:18.01+00:00
@Jenn - Becca JBRealtors
Hi,
Sorry I need to ask a few questions in order to get some more information.

Since you added the "office-exchange-server-connectivity" tag to this question,do you have an Exchange on-premises server? Or are you using Exchange Online(Office 365)?

Do you have problem with sending to a certain domain? Or are you not able to send to all domains (gmail for example)?

Did you receive some NDR messages in Outlook?Please post a screenshot if possible. (Note:please remember to remove your personal information in the screenshot for security)

Have you tried bypassing the CRM system and sending the mails? If it works fine, the problem should not be on the Outlook's side.

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Jenn - Becca JBRealtors 1 Reputation point

2020-12-16T15:04:48.173+00:00

I work off of an Outlook application on my computer so I'm assuming that means I use Office 365 (I have word, powerpoint, excel, etc, like it's a package?). I am computer dumb and didn't see any tags that looked like English, so I chose something I recognized, sorry!
2.) and 3.)They are multiple domains. Also, if one email made it through and someone responded (we sent to roughly 60 people from CRM), when I would reply, it would come back undeliverable at that point. 48812-undeliverable-testing-1234.pdf
4.) Ok, so I sent out an email to 10 people at a time and a few came back undeliverable. So, I did some digging and a computer tech from a local shop said if you send a large amount of people 1 email, Outlook will mark you as a spammer and blacklist you from emailing like that? Now, if it helps, we are not spammers and are only sending to our past clients and people we talk to on a regular basis
Kael Yao-MSFT 37,496 Reputation points Microsoft Vendor

2020-12-17T06:57:56.903+00:00

Hi,

Thanks for the detailed information.I think you should be using Office365.
From the NDR message,it also seems to have something to do with being tagged as spam.
Can you find some messages in the inbox or junk folder asking you to verify your office365 account?

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Kael Yao-MSFT 37,496 Reputation points Microsoft Vendor

2020-12-21T09:41:36.253+00:00

Hi,
I am writing here to confirm with you how thing going now?
Was the problem resolved?

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