Email deliverability is one of the most common questions we get. This guide covers why emails end up in spam or promotions folders, what you can do about it, and how Check Cherry handles email behind the scenes.
Start here: check your delivery status
Before troubleshooting, check the message status in Check Cherry. We show you whether a message was delivered, opened, bounced, or deferred.
- Delivered: The email reached their mail server. If they can't find it, it was filtered into another folder like Promotions, Spam, or Junk on their end.
- Bounced: The address is invalid or their server rejected it. See understanding bounce errors.
- Deferred: Their server is temporarily delaying it. This usually resolves on its own within a few hours.
This is the fastest way to narrow down what is actually happening.
The most common issue: corporate, school, and government emails
This deserves its own section because it is by far the most common deliverability complaint we hear.
Here is what is happening: you have been emailing a corporate buyer from your personal email. You agree on the details, you send a proposal through Check Cherry, and it goes to spam. The client says "I never got it."
The reason is that your proposal email came from a different address than the one they have been talking to. Corporate, school, and government organizations often use dedicated security services to filter incoming mail. These filters are more aggressive than what Gmail or Yahoo use. They look at the sender address, the domain, and whether they have seen email from that sender before. A first-time email from an unfamiliar sender with a link and an attachment is exactly the kind of thing these filters are built to catch.
What you can do
- Warm up the connection before sending the proposal. Send a simple, low-key message from Check Cherry first. Something like "Hi, I'm going to send over a proposal for your event. Just wanted to make sure you're receiving emails from this address." Once they reply, your future Check Cherry emails are much less likely to be flagged.
- Ask them to check spam or junk. If they find it, marking it "not spam" trains their filter for future messages.
- Ask them to add your sending address to contacts. This whitelists you.
- Use the proposal link instead. Copy the proposal link and paste it into an email you send from your personal inbox. The client clicks the link to view and accept. No spam filter issues because the email comes from you.
General deliverability tips
If you are experiencing general deliverability issues (not just corporate clients), it is likely related to your sending patterns or email content.
- Send fewer automated follow-ups. Sending too many automated emails in a short period can trigger spam filters. Space them out and only send what is necessary.
- Simplify your emails. Heavy images with little text look like marketing emails to spam filters. Keep early emails text-focused.
- Check your sending patterns. If you are sending bulk automated messages, review the frequency. One email per week per client is plenty for most businesses.
- Avoid all caps or excessive punctuation in subject lines. These are classic spam indicators.
- Make sure your email content is relevant. Emails that recipients consistently ignore (no opens, no clicks) can hurt your sending reputation over time.
About Check Cherry's email infrastructure
Check Cherry follows industry best practices for email authentication, including SPF, DKIM, and DMARC. These are the technical standards that help email providers verify that messages are legitimate.
Our sending reputation is healthy. Our spam complaint rate averages well below 0.1%, and our sending IPs and domains are in good standing with all major email providers. Deliverability issues are almost always on the recipient's end, not ours.
Outlook, Hotmail, and Live.com
Microsoft's email services (Outlook.com, Hotmail, Live.com) sometimes temporarily delay emails from legitimate bulk senders. This is a known behavior that affects thousands of businesses, not just Check Cherry. When this happens, the email usually arrives within a few hours. If a recipient using one of these services reports a delay, try resending the message.
Open and click tracking
Check Cherry tracks whether emails are opened using a tiny invisible image embedded in each message. When the recipient's email app loads images, we know it was opened. Click tracking works by routing links through our server so we can record when someone clicks.
Some things to keep in mind:
- Some email apps auto-load images in preview, which counts as an "open" even if the person did not actually read the email.
- Apple Mail's privacy features can pre-load tracking pixels, making open rates appear higher than actual.
- Corporate security programs sometimes click links automatically to check if they are safe, which can cause false click reports.
For more details on tracking, see why emails show as opened when they were not.