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Just because this happened to me when we tried doing the same kind of thing----
I ran into a problem trying to send out a Holiday email to all of my 800 tenants. It turned out that our web hosting (which included our company email accounts) had a limit of how many emails it could send per day. I learned that our email account includes "250 SMTP relays per mailbox, per day" so my mass email kept failing. It wasn't Sitelink that caused the issue, we had to talk to our web hosting people.
Capitola brings up a good point, depending on who your server host is will make a big difference. When I got to the store i'm at now we had that issue and I finally realized it was godaddy's silly limits of I think it was 125 per 24 hours. We have 996 units, you do the math on how bad that DOES not work, especially when sending collection emails at the first of the month. I switched us to office 365, still have a limit of how many per minute but it's more of a way to make sure someone isn't sending spam email to thousands of people via their server.
If you're trying to send a blanket email to all those with an email on file you could goto Company>Setup> CRM Campaign Schedule and create one for whatever it is you're needing. For instance we do bi-monthly garage sales here so I have one created with the info in it and I just change the date as needed.On the other hand if you're wanting to send something such as a past due notice you would want to do it under Company>Setup> Past due Schedule
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