Ever had one of those days when your email stats go haywire, and you’re left scratching your head? Yep, that was me last month. Everything looked fine—sales were coming in, servers running smooth—and yet, email bounces were through the roof. Orders were being placed… but receipts weren’t being received. After digging into it, I found the surprising culprit: VPNs. Let’s talk about how it happened and what we did to fix it—without losing a single sale.
Contents of Post
TL;DR
VPN-using customers triggered email blocks due to suspicious IP activity. This led to bounce spikes, especially for transactional emails like receipts. We fixed it with smarter bounce handling, a flexible retry system, and safe fallback logic. Now emails either go through or a failover ensures the customer still gets their receipt—just in time.
Chapter 1: The Mystery of the Vanishing Emails
At first, we didn’t notice anything wrong. Orders were being placed normally. But our email bounce reports told a different story. Bounce rates were up—way up. Weirdly, it was only receipt emails affected. Promotional emails, newsletters, and alerts were fine.
So we pulled a sample of affected orders and manually checked their email activity. The result? Nada. Zilch. It was like throwing emails into a black hole.
🚨 Clue #1: Every single one of these failed messages was tied to orders placed from suspicious or unusual IP addresses.
Digging even deeper into the logs, we saw a pattern: those IPs belonged to commercial VPNs.
Chapter 2: VPNs – Friend or Foe?
Using a VPN isn’t bad. In fact, it’s pretty smart. Some people just want privacy. Others might be ordering gifts while traveling or shopping during lunch breaks in the office.
But here’s the problem:
- Email providers like Gmail and Yahoo see traffic from VPN IPs as suspicious.
- If too many emails go out from one IP and bounce, those IPs get rate-limited or blocked.
- Especially if the destination inbox thinks “this sender looks fishy.”
That’s exactly what was happening here. Imagine you order something small through your VPN—say, a phone case. Our system would send your receipt instantly. But your inbox sees it coming from an IP that’s been flagged and, well… bounce city.
Chapter 3: Bounce, Retry, Repeat
Once we figured out the VPN link, the next question was: how do we make sure the customer still gets their receipt?
Most platforms treat a bounce like an ex. You’re blocked, and that’s it. But not our house. We designed a bounce strategy with a soft heart 🫶 and an engineering brain 🧠.
Here’s our updated process:
- Step 1: An email is sent after checkout.
- Step 2: If it bounces, we categorize the bounce as soft (temporary) or hard (permanent).
- Step 3: For soft bounces, we retry up to 3 times on a delay: 5 min, 30 min, 2 hrs.
- Step 4: If it fails after retries, we mark the status as “Held” and trigger a safe fallback.
What’s the fallback? One of three things, based on user state:
- If they’re a logged-in user, a notification appears in their account dashboard with a link to download the receipt directly from us.
- If they used social login or a guest checkout, we generate a temporary, secure link tied to their order number and email and resend that via a masked sender.
- In critical cases, our support team gets flagged and we either phone call (yes, really) or SMS-text the user a secure download link.
Sounds like a lot. But it runs like a charm.
Chapter 4: Keeping Your Sender Score Squeaky Clean
Bounce rates matter. A high bounce rate can put your entire domain at risk. If you’re marked as a spammy sender, even your legit emails don’t make the inbox.
To stay in good standing, we had to make sure:
- We weren’t sending more retry messages than needed.
- All retries used alternate sending domains and IP pools to avoid continued blacklisting.
- We implemented feedback loops with major providers like Gmail and Outlook.
As a bonus, we now monitor VPN order flags and can assess the “email health risk” of traffic in real-time. If bounce potential is high, the system queues messages and spaces them out to avoid spikes.
Basically, we turned a fire drill into a firewall. 🔥🛡️
Chapter 5: Lessons We Learned
This little bounce spike taught us a lot. And we’re better for it. Here are our biggest takeaways:
- Not all bounces are bad. Some are just misunderstood. Look deeper.
- VPN orders aren’t your enemy. But they need extra care when emailing.
- Bounce retry logic is your safety net. One failed email doesn’t mean a lost sale—unless you ignore it.
- Fallbacks build trust. When customers see that you care enough to reach them, they remember.
Also, and this is huge: our support tickets related to “Hey, did I get a receipt?” dropped by 85% in two weeks. Talk about sweet results.
Chapter 6: Where We Go From Here
We’re now working on smarter geo-IP detection that doesn’t just identify VPNs, but predicts if they’re likely to trigger a bounce. With that, we can switch to delay-send methods or even route the email through a sender with stronger reputation in that geo.
We’re even experimenting with inline receipts—displaying the receipt on the order confirmation screen so even if delivery fails, the info was already seen.
Because let’s face it: receipts are critical. Customers count on them. Refunds, expense claims, return policies—none of those can move without proof of purchase.
And when stuff goes missing in the email black hole? You better believe they’ll be back, and probably mad.
But not anymore. Whether you’re shopping from a bunker, Bali, or your breakroom—if you order from us, you’ll get your receipt. One way or another.
Final Thoughts
If you run an eCommerce platform or transactional system, don’t wait for bounce spikes to ruin your day. Plan for failure, automate responses, and always have backup routes. Bounce handling might not be sexy—but losing trust definitely isn’t.
Happy emailing!