Sending Bulk Emails From Office 365 – How to send bulk emails in Gmail and Outlook that feel personal 5 steps to look cool instead of awkward
Want to send bulk emails from your Gmail or Outlook inbox… and look great in front of your email recipient audience? 😎
Sending Bulk Emails From Office 365
There are many ways to send bulk emails, so let’s summarize which ones exist and show you which option is right for you. 😄
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We all know this method of mass mailing. It’s quick and easy, but often leads to awkward results. And it doesn’t look very professional.
Also, you have to play around with copying the list of recipients into the BCC field correctly, and the number of these recipients is always limited.
In short: this is almost never the right choice. If you don’t have time or don’t care, you will definitely look unprofessional. 😟
Need to send a bulk email to over 2,000 people today (and is it really necessary today and today only)? Then this might be your choice. If not, go to option 3!
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If you’re ok, check out our guide to using MailChimp (which is what we use for our email marketing).
If you want to send bulk emails that feel personal and are more likely to be read, we’ll talk about that now. 👇
Need to send a bulk email that feels personal to hundreds or thousands of people at once? Then this is your choice for sure.
Use a platform (like Salesflare) that connects to your inbox and sends personalized emails at a scale that is indistinguishable from the emails you send manually one by one (If you can’t wait: 5 easy steps for that below ! ).
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One limitation with all this power is that with services like G Suite (professional Gmail) or Microsoft/Office 365 (Microsoft’s rival email service), you can send up to 2,000 emails per day. If you need to send more emails, the platform will (in most cases) spread them out over several days.
What if you want to make sure people respond (or open or click) and you want to email them multiple times until they do?
Here are some common reasons why our customers choose this (click to watch the guide on YouTube):
Do you want to be a professional? Creating a sequence of emails instead of just one is step 4 (optional) in our guide. 👇
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We’ll show you how to do this with Salesflare because it’s software we created and use ourselves, and because it has several advantages:
Not sure about using Salesflare? Don’t worry, like I said, the steps are the same across platforms, so let’s dive in. 🤓
To send bulk emails from your Gmail or Outlook mailbox using the platform of your choice, you need to connect your mailbox first. With Salesflare, this is the first thing you do when you sign up.
For the former, it may be better to use a platform like Salesflare, which offers bulk email and CRM in one place. This will avoid a lot of unnecessary work.
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In the second case, you can integrate these other systems with your email platform. Our customers, for example, use Zapier or Piesync for this purpose.
Just the full name for everyone? No problem. Salesflare will automatically split it into first name, middle name, last name, prefix and suffix. Therefore, you can personalize your email without any problems.
Write the email as if you were sending it to one specific person, and then replace certain words (like their name, company name, and whatever) with the combined fields.
And, if you use Salesflare, you can also see if the same people who clicked on links in your emails visited your website, which pages they viewed, when and for how long. Just install the script which you can find in Salesflare settings here.
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I wonder what it can be used for? Watch this use case video from our customer on Youtube.
Ready to sail? Maybe a quick test email to make sure (just hit “submit test” in Salesflare) and then… off to the inbox!
Just create a visual funnel with the steps you need to bring people. This will give you the visibility and control you need to close as many trades as possible.
Want to learn more about how to do it successfully? Just read our guide on how to build a strong sales funnel and manage it like a pro.
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Do you have any questions afterwards? Contact us via chat in our app or on our website! We are prepared to assist.
I’m the co-founder of Salesflare, the only powerful CRM for small businesses. I love growth, sales automation and creating beautiful products. Microsoft explains that Exchange Online is not a bulk mail platform. There are restrictions to prevent people who want to send bulk emails (spam) or have their mailboxes hijacked by malware. In fact, even though Microsoft recently increased the maximum limit of recipients per message from 500 to 1000, that doesn’t mean you should switch bulk email to Exchange Online from a commercial email platform like Mailchimp.
Most of the time, my mailbox never gets the attention of monitoring tools looking for evidence of abuse. I usually don’t send enough emails to reach the limit. But sometimes I need to send a message to a fairly large mailing list (200 to 600 members). I want to know when Exchange Online pauses.
The documented limit for accounts with an Office 365 E3 or E5 license is 10,000 recipients per day. A tenant-managed mailing list (not a private list) counts as one recipient. Managing mailboxes by measuring the number of messages they send is a crude control mechanism. Exchange Online Protection uses smarter algorithms to detect unusual activity that may indicate something is afoot. The settings Microsoft uses to detect problem senders are not documented (as you might expect), but you can force Exchange Online Protection to take an interest in your sending activity.
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For example, if someone who normally sends 10-15 messages a day suddenly sends 200 messages in a short period of time, or suddenly starts sending messages to a large mailing list, they may have been told to send a message about something like a new price list for customer. One event is not enough to raise suspicion, but there may be other signs that increase the confidence that something is wrong. For example, because hyperlinks can lead the unwary to bad places, messages containing links are more suspicious than plain text messages.
A spike in mailbox traffic may not be serious, but if observed mailbox behavior deviates significantly from expected rates over time, then the account may be compromised and action is required. To ensure that potentially compromised accounts cannot be used to send spam or malware, Exchange Online Protection limits (blocks) mailboxes. This means that users are allowed to send messages to internal recipients, but not to external recipients, including mail contacts and guest users registered in the tenant directory.
I tested the theory by sending several emails throughout the business day containing a hyperlink to a mailing list. Of course, after sending the message to about 2,500 recipients spread across multiple distribution lists, Exchange Online Protection decided that was enough and blocked my mailbox. When blocking is applied, Exchange Online generates an NDR (Figure 1) for each external message that the user tries to send. The text of the message is:
“Your message could not be sent because you have not been identified as a valid sender. The most common reason for this is that your email address is suspected of being spam and is no longer allowed to send emails. Contact your email administrator for assistance. The remote server returns “550 5.1.8 Access denied, invalid outgoing sender”.
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Events registered for alerts that generate notifications for administrators. “User prevented from sending email” is one of the standard alert policies created by Office 365 to notify administrators about problems in tenants.
To investigate and unblock restricted accounts, administrators navigate to the Restricted Users section of the Security & Compliance Center to review the current list of blocked users (Figure 2). In this scenario, the account (my) is restricted because Exchange Online Protection has detected a high percentage (20.75%) of suspicious messages in the last 24 hours.
The total number of outgoing messages is 36. Both figures are not entirely clear; 747 divided by 36 equals 20.75, which is the percentage of spam messages. Microsoft needs to do some work to refine the reported data and make it more accurate.
If you recognize an account that is locked and you know it shouldn’t be locked, you can unlock the account using the Security & Compliance Center or PowerShell. Here’s how to do it with
Deploy And Configure Microsoft Office 365 With Area 1 As Mx Record · Cloudflare Area 1 Email Security Docs
I don’t see audit events logged when the account is unlocked. An unlocked account cannot send messages immediately because the mail server that processes outgoing messages needs to be updated.
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