You've heard it before. Maybe last week.

"I never got your proposal."

And you probably thought: they went with someone cheaper. They weren't serious. They ghosted me. But what if they were telling the truth?

SingleOps has an entire support article in their knowledge base titled "Avoiding Email Spam Filters." In it, they acknowledge that proposals, invoices, and reminders sent through their platform can be flagged as spam. They actually recommend that when you send a proposal onsite, you ask the customer to check their email right then, and if it didn't arrive, have them check their spam folder and mark it safe.

The software company sending your proposals tells you to have customers check spam in real time, because the platform itself can't fully prevent this from happening.

And SingleOps warns about something else most users miss: recipient email servers don't send you any notification when they filter your email to spam. No bounce or error. Your CRM says "sent." The customer never sees it. You never find out.

It's not just SingleOps. Over on Capterra, reviewers have documented 40+ specific instances of Arborgold email delivery failures causing lost bids and customer confusion. One user on Software Advice reported that Arborgold displays a pop-up saying "email sent successfully" whether or not the email was actually delivered. They called it "deceitful and misleading." Arborgold has acknowledged email delivery issues in their own support documentation, but the problem doesn't appear to be fully resolved.

So how widespread is this? According to EmailToolTester's 2026 analysis of 15 email service providers, the average inbox placement rate was 83.1%. That means roughly 1 in 6 business emails never reach the inbox. 10.5% land in spam. 6.4% vanish entirely with no trace.

Your commercial clients are getting hit hardest. GlockApps reported that Office365 inbox placement dropped over 26 percentage points year over year in Q1 2025. Outlook dropped 22.56 points. Property managers, municipalities, HOAs, commercial property companies are overwhelmingly on Microsoft email. Your biggest, highest-value clients are now the hardest inboxes to reach.

A lost proposal is a $5,000 to $15,000 job that went to whichever competitor got their quote through first. It's a crew with a gap in the schedule because the pipeline came up short. It's revenue that disappeared without a notification, without a bounce, without any signal at all.

When's the last time you actually confirmed a customer received your proposal? Not the sent confirmation in your CRM, but whether the email actually landed in their inbox, where they could see it.

Before you fix anything, test it:

Go to mail-tester.com. Copy the temporary email address it gives you. Go into SingleOps or Arborgold and send a test proposal to that address Go back to mail-tester.com and check your score If you score below 7 out of 10, you've got a deliverability problem right now

Two minutes. You'll know where you stand.

If Your Score Is Low, Here's What's Probably Wrong

There are three authentication records your domain likely needs: SPF, DKIM, and DMARC. These records prove to Gmail, Outlook, and Yahoo that your company actually sent this email and it's not spam pretending to be you.

Think of it like a return address on a letter, plus a wax seal, plus a stamp from the post office confirming you're legit. Without those three things, email providers increasingly assume your messages are junk.

Google and Yahoo mandated these records for bulk senders starting February 2024. Microsoft followed in May 2025. If your domain doesn't have them, your emails are getting filtered or rejected. According to Fortra's Q2 2025 data, fully authenticated domains achieve 2.7x higher inbox placement compared to unauthenticated ones. And only about 33.4% of the top 1 million business domains even publish a valid DMARC record.

Log in to your domain registrar (GoDaddy, Namecheap, wherever you bought your domain). Go to DNS settings. Check if you already have SPF, DKIM, and DMARC records. Use MXToolbox.com to check for free. If they're missing, add them. Your CRM's support docs will have the exact records to paste in. SingleOps and Arborgold both have documentation on this. If you're not sure, your web person or IT provider can handle this in one sitting.

In SingleOps, watch how your email templates are configured. Too many links and images in a proposal email can trigger spam filters. Use the visit reference number formula to make each email unique so filters don't flag them as bulk sends. And SingleOps explicitly warns: "Do not use SingleOps for marketing." If you're sending promotional emails through your CRM, you're probably damaging deliverability for your actual proposals. Use a separate tool like MailChimp for marketing emails.

SingleOps also notes that engagement-based filtering (used by Gmail, Yahoo, and Hotmail) means low open rates on past emails can cause future emails to be spam-filtered automatically. So every proposal that lands in spam makes the next one more likely to land there too.

In Arborgold, check your email service partner settings. This is where deliverability often breaks down.

If domain authentication feels over your head right now, here's the immediate backup: send proposals from your own business email (Gmail, Outlook) instead of through the CRM. Use the CRM only for record-keeping. It's not ideal long-term, but it gets your proposals delivered today while you sort out the DNS records.

Hand this entire section to whoever manages your email or your website. They can do this in one sitting.

Action Steps

Tools worth bookmarking:

Google and Yahoo rolled out mandatory email authentication requirements in February 2024. Microsoft followed in May 2025. If your domain doesn't have the right records, your emails are increasingly likely to land in junk or get rejected outright. The bar keeps moving.

The tree services that fix this now will have a quiet advantage over every competitor still scratching their head wondering why customers "never respond." The customer probably wasn't shopping you on price. They just never saw your proposal.

Do you actually know how many of your proposals arrived last month? Or are you just trusting the "sent" status in your CRM and hoping for the best?

Go to mail-tester.com today. Send a test proposal from your CRM. Check the score.

If it's below 7, fix it this week. Every day you wait is another proposal that might be sitting in someone's spam folder right now.

If you've tested your deliverability and found problems (or if you've already fixed them), hit reply and tell us what you found. We're tracking this issue across the industry and your experience helps every owner on this list.

See you all next week!
-Jacob Hastings

The Backcut