I’m having a major problem with my email system right now and getting nowhere with support.
When I try to send emails through my platform, all the links inside those emails stop working completely. Users get a security warning that pops up saying the SSL certificate has been expired for over a month now.
After doing some digging into my domain settings, I found out that my platform uses Mailgun to handle email delivery, and it looks like Mailgun runs on Google’s infrastructure.
My SSL cert was originally set up back in November 2023. Most SSL certificates are good for about 24 months, so the timing makes sense for why it would be showing as expired now.
The frustrating part is that this isn’t something I can fix on my end. The email service provider needs to generate a new certificate or renew the existing one for my domain.
I’ve been going back and forth with support but they keep acting confused about the whole SSL situation. It’s like they don’t understand how certificates work with email services.
Has anyone else run into this same problem before? I really need to get my email links working again.
Ugh, third-party email services are the worst when they break. Mailgun’s usually solid, but SSL issues mess up everything. Hit up their Twitter support - social teams often escalate faster than regular tickets. Also check if you’ve got backup MX records set up for your domain. Might route around the SSL problem while they fix it.
SSL cert failures on email infrastructure are brutal - you’re stuck waiting while your business stops working.
Stop depending on single email providers for critical stuff. When Mailgun’s cert breaks, you need immediate failover.
I build email systems that monitor cert health and auto-switch providers when things break. Set up health checks that ping your email links every few minutes - catch SSL failures before users notice.
When the primary provider dies, the system instantly routes through backup SMTP services. No waiting for support tickets.
The monitoring logs cert expiration dates across all your domains so you can bug providers about renewals before they break. Way better than discovering problems when users start calling angry.
I use Latenode for these failover systems - you can connect multiple email providers and create smart routing logic. Takes 30 minutes to monitor all your email infrastructure.
Next time Mailgun breaks, your emails work through the backup while they fix their cert mess.
Check your DNS records - Mailgun sometimes pushes new CNAME entries for certificates that need manual approval. I had similar SSL warnings last year and found stale DNS validation records were blocking cert renewal. Log into your domain registrar and check for pending validation requests or TXT records that need updating. Also test if this affects all email links or just specific subdomains - helps narrow down which cert expired. While waiting for support, send test emails to Gmail and Outlook to see if SSL warnings show up across different clients. Sometimes it’s just certain email security policies, not a complete cert failure.
Your timeline confirms it’s definitely a cert renewal failure. Email service SSL certs usually auto-renew through Let’s Encrypt, but when that automation breaks, you get exactly these symptoms. I’ve hit this twice - once with SendGrid, once with a smaller provider. The trick is getting past their front-line support since regular agents don’t get certificate infrastructure. When you contact them, say ‘SSL certificate expired on email delivery subdomain’ and ask for DevOps or infrastructure team immediately. They usually have a separate ticket system for infrastructure that skips normal support entirely. Also check your domain’s DNS records - they might need you to update CNAME records for new cert validation. Worst case, this could take two weeks if they need to manually provision new certs across their infrastructure. I’d set up an alternative SMTP relay temporarily so you can keep sending emails while they fix this.
Been there. SSL cert issues with email providers are a nightmare when you can’t control the infrastructure.
Don’t wait for support to figure it out. Most providers have automated cert renewal, but when it breaks, it really breaks.
Consider building your own email automation instead of relying on managed services. I switched after getting burned by provider downtime and cert issues.
What saved me was using Latenode to create email systems I actually control. You can connect multiple providers as backups, monitor SSL issues, and automate cert checking.
I built a workflow that tests email delivery and switches providers if there are SSL problems. No more waiting on support tickets.
Takes maybe an hour to set up, then you never worry about this again. Way better than email provider roulette.
Same thing happened to me with a different email provider about six months back. Their SSL cert expired and broke all email links - exact same security warnings you’re seeing. The support confusion is pretty typical. Most first-level agents don’t really understand how SSL certs connect to email delivery. When I escalated to their tech team, turns out their auto-renewal failed for several domains including mine. What worked: I sent them specific screenshots of the SSL errors and asked to skip regular email support and go straight to their infrastructure team. I also mentioned potential compliance issues, which seemed to light a fire under them. Meanwhile, I switched to a backup SMTP service to keep things running. Took about 10 days total to fix, but they issued the new cert within 48 hours once the right people got involved. Document everything - infrastructure failures like this usually qualify for service credits.