Quick Summary
If proposals to corporate, school, or government clients are going to spam or the Promotions folder, you're not alone. Their email filters are aggressive and there's no easy fix on our end, but there are workarounds below that can help.
If you're having general deliverability issues with leads and clients, it's likely related to your sending patterns or message content. Reducing automated follow-ups and simplifying your emails usually makes a difference.
Check Cherry's sending infrastructure is in good standing. Our spam complaint rate averages well below 0.1%, our IP and domain reputation are consistently rated high by Google Postmaster Tools, and our authentication (SPF, DKIM, DMARC) runs at 100% success.
First: Check your delivery status in Check Cherry
Before troubleshooting, check the message status in Check Cherry. We show you whether a message was delivered, bounced, or opened.
If it shows "delivered" - the email got to their mail server. It's being filtered on their end into spam, Promotions, or another folder. That's a different problem than "not delivered" and the tips below will help.
If it shows "bounced" - their mail server rejected the message. This is usually an invalid email address or a full mailbox.
If open tracking shows they opened it - they received it. They may have just missed it or forgotten to respond.
This is the fastest way to narrow down what's actually happening.
If a proposal went to spam or the Promotions folder for a corporate, school, or government client.
This is by far the most common deliverability complaint we hear, and it deserves its own section.
Here's what's happening: You've been emailing a corporate buyer from your personal email. You agree on the details, head over to Check Cherry, create the proposal, and hit send. The buyer's email system has never seen checkcherry-mail.com before, and the very first email from this unknown domain is asking them to sign a contract and make a payment. To a corporate spam filter, that looks suspicious.
Corporate, school, and government organizations often hire dedicated security services to filter their email. These services tend to have aggressive settings, and when employees complain about spam, the easiest thing for an IT department to do is tighten the filters further. That affects all incoming email, including your legitimate proposal.
What you can do:
Instead of sending the proposal as the very first email from Check Cherry, send a simple, low-key message first - something like "Thanks for chatting today! Just reply to this message and I'll send over that proposal."
Warm up the connection before sending the proposal. This is worth trying, especially for corporate clients. Instead of sending the proposal as the very first email from Check Cherry, send a simple, low-key message first - something like "Thanks for chatting today! Just reply to this message and I'll send over that proposal." When they reply, their email system now has a history of back-and-forth with checkcherry-mail.com, and the recipient has actively engaged with the domain - one of the strongest positive signals a spam filter can see. Your proposal then arrives in the context of an existing conversation rather than as an unsolicited first contact asking for money. Google's own sender guidelines confirm that "messages from recipient contacts are less likely to be marked as spam." We can't guarantee this will solve the problem - every corporate mail system is different - but it's based on how spam filters generally work and it's worth a shot for high-value clients.
Give them a heads-up before you send. A quick text or call "I'm about to send the proposal through my booking system, keep an eye out" goes a long way.
Ask them to check spam/junk and mark your message as "Not Spam" or add the sender to their contacts. This trains their filter for future messages.
Ask their IT team to whitelist checkcherry-mail.com if this is a repeat client.
Share the link directly. Every proposal in Check Cherry has a "Copy Link" button at the top. You can paste that link into a text message or send it from your personal email as a backup.
Try SMS. If you have Twilio set up, you can send proposals via text message and skip email entirely for difficult-to-reach clients.
A note on all of this advice: email deliverability is inherently unpredictable. These tips are based on how email filters generally work, and we've seen them help, but because we don't control the recipient's mail system, we can't promise any single change will fix the problem. What we can do is stack the odds in your favor.
If you're experiencing general deliverability issues, it's likely related to your sending patterns or content.
If emails to leads, clients, and bookings are consistently not getting through, the issue is more likely on the sending side. Email service providers like Gmail, Yahoo, and Outlook have become very good at filtering. They don't just look at your emails -they look at how other recipients have responded to similar messages across their entire network. This is machine learning at scale.
Think of Gmail less as a "spam filter" and more as a placement algorithm. It's trying to be helpful by putting messages where it thinks they belong - Primary, Promotions, Updates, or Spam. A proposal with a call to action ("accept this proposal," "choose a template") can look a lot like a promotional email to these algorithms.
Here are the most common patterns we see with accounts that have deliverability issues:
Too many automated follow-ups. Check Cherry makes it easy to set up automated messages, and that's a powerful feature. But if a lead isn't responding after 2-3 follow-ups, more emails aren't going to change their mind - and they may be hurting your deliverability. We've seen accounts sending a daily automated email for 30 days straight after someone books. That's too much. Consider reducing the number of automated follow-ups you send to leads and proposals.
Image-heavy emails with little text. Sending a flyer or graphic as the entire email body is a common spam signal. Your messages should have a healthy balance of text and images.
Emails with nothing but a link. We've seen accounts where the entire email body is just a bare link to a booking page - no greeting, no context, no business info. That's exactly what a phishing email looks like. Add some context about who you are and what they're clicking on, and use descriptive link text like "View your proposal" instead of pasting a raw URL.
Spammy-looking content. Different font sizes, lots of colors, ALL CAPS, excessive exclamation marks, dollar amounts, words like "free" or "discount"- these all trigger filters. They compare your content against spam they're currently seeing across their network.
Mixing content types. Gmail's own documentation says not to mix different types of content in the same message - for example, don't include promotions in a payment receipt. They want to categorize your message accurately, and mixing types confuses their algorithm.
Try turning off email tracking in Check Cherry.
This is the one thing you can change right now in Check Cherry that may improve deliverability.
Check Cherry can track email opens and link clicks, but this works by embedding a tiny invisible tracking pixel and rewriting your links through a tracking server. Spam filters specifically look for these patterns - they're hallmarks of marketing and mass email.
If you're experiencing deliverability issues, try disabling email tracking under Manage --> Business Settings. This will impact all email sent from Check Cherry. You'll lose open and click stats, but your emails will look more like personal business correspondence to spam filters. You can always turn it back on later.
More tips for better inbox placement
Respect the inbox. Before adding another automated email, ask yourself: is this helpful to the recipient? Less is more.
Don't nag via email. One, two, maybe three follow-ups is fine. If they're not responding to email, they're not going to respond to more email. Pick up the phone.
Make messages look personal. Use their name, reference their event, write conversationally. The more your email looks like a 1:1 business conversation, the better it performs. Check Cherry makes it easy for you by including dynamic value tokens that you can paste into the body of your message templates.
Use clear, honest subject lines. Subjects are important to deliverability. Avoid misleading or vague subjects.
Don't mark internal messages as spam. If your staff is getting lead notification emails and marking them as spam because they don't want to see them, that damages your sending reputation. Use filters or notification settings instead.
Don't upload purchased lead lists. If someone didn't give you permission to email them, you're not in compliance with CAN-SPAM law. This is most common with wedding show attendee lists - those people didn't visit your booth and don't know you.
About the Promotions tab
One thing that surprises a lot of people: Gmail considers all tabs -Primary, Promotions, Updates, and Forums - as inbox placement. If your email lands in the Promotions tab, Gmail considers that successfully delivered. It's not spam.
That said, we know most people think of "inbox" as the Primary tab, and they may not check Promotions regularly. There's not much anyone can do about Gmail's tab sorting - it's driven by machine learning based on the content of the message and how Gmail users across their network interact with similar messages.
If a client says they didn't get your email and they use Gmail, it's worth asking them to check the Promotions tab.
What Check Cherry does on our end
Email deliverability depends on both Check Cherry and you as a sender. Here's what we handle:
Proper email authentication - SPF, DKIM, and DMARC are configured and monitored. We maintain 100% success rates on authentication.
Dedicated IP addresses - Our IPs are only shared among Check Cherry customers, not with other companies or services.
Subdomain isolation per account - Each Check Cherry account sends from its own subdomain of checkcherry-mail.com. This means if one sender develops a poor reputation, it's isolated to their subdomain and doesn't drag down deliverability for other customers. Most platforms don't do this.
IP and domain reputation monitoring - We monitor Google Postmaster Tools and other services daily. Our IP reputation and domain reputation are consistently rated high.
Spam rate monitoring - We track spam complaint rates closely. Our rates are very low, with many days having zero complaints.
No bulk email - We don't allow mass email or bulk lead uploads through Check Cherry. This protects the sending reputation for everyone on the platform.
Quarantine system. We proactively detect and address problematic sending patterns before they affect other customers.
CAN-SPAM compliance - All messages include required identification and unsubscribe options.
It's important to understand that all Check Cherry customers share sending infrastructure. Good sending habits from everyone on the platform help everyone. Problematic sending from one account can affect deliverability for others - which is why we take monitoring and enforcement seriously.
What Check Cherry cannot do
We can't guarantee 100% inbox placement. No one can - not us, not Gmail, not any other platform. Email placement algorithms are constantly changing, and they're never 100% accurate. What we can guarantee is that we follow every best practice, maintain clean infrastructure, and give you the tools and education to maximize your chances.
If you're experiencing persistent issues, reach out to our support team. When you do, it helps to include:
- The recipient's email address (so we can check delivery status on our end)
- The approximate date and time the message was sent
- Whether the message shows as "delivered" in Check Cherry
- Any error messages or bounce notifications you've seen
This helps us investigate quickly and skip the back-and-forth.