How I Would Fix emails landing in spam in a Circle and ConvertKit AI chatbot product Using Launch Ready.

How I Would Fix emails landing in spam in a Circle and ConvertKit AI chatbot product Using Launch Ready

The symptom is usually simple: users sign up, get the chatbot flow, but the email ends up in Promotions, Spam, or never arrives at all. In a Circle and ConvertKit setup, the most likely root cause is not "the AI chatbot" itself. It is usually domain authentication, sender reputation, or a broken handoff between your domain, ConvertKit, and any redirect or tracking layer.

The first thing I would inspect is the sending domain setup in ConvertKit and the DNS records on the live domain. If SPF, DKIM, or DMARC are missing or misaligned, inbox providers will treat your mail as risky even if the content is fine.

Triage in the First Hour

1. Check the exact failing email path.

• Is this a welcome email, chatbot follow-up, onboarding sequence, or password reset?
• Note which recipient providers are failing: Gmail, Outlook, Yahoo, Apple Mail.

2. Open ConvertKit sender settings.

• Confirm the sending domain.
• Confirm whether DKIM is verified.
• Check whether SPF includes ConvertKit.
• Review bounce and complaint rates.

3. Inspect DNS at the registrar or Cloudflare.

• Verify SPF TXT record.
• Verify DKIM CNAME or TXT records.
• Verify DMARC policy and reporting address.
• Check for duplicate SPF records or old mail vendors still listed.

4. Review Circle email-related settings.

• Check what domain Circle uses for links and notifications.
• Confirm any custom domain or subdomain is active and resolving correctly.
• Look for broken redirects that can hurt trust signals.

5. Check recent changes.

• New domain?
• New sending address?
• Recent migration from another ESP?
• Changed subdomain, Cloudflare proxy mode, or SSL config?

6. Inspect content and links in one failed message.

• Spammy subject lines?
• Too many links?
• Mismatched link domains?
• Images with little text?
• URL shorteners?

7. Test deliverability from two inboxes.

• Gmail test account
• Outlook test account
• Compare headers and spam placement.

8. Review logs and monitoring.

• Bounce logs
• Complaint logs
• Uptime status for redirect domains
• Any 4xx/5xx responses on linked pages

dig txt yourdomain.com
dig txt _dmarc.yourdomain.com
dig txt k1._domainkey.yourdomain.com

Root Causes

| Likely cause | What it looks like | How I confirm it | | --- | --- | --- | | SPF missing or wrong | Mail sent but flagged as unauthenticated | DNS lookup shows no SPF record or no ConvertKit include | | DKIM not aligned | Message says "signed by" one domain but "from" another | Email headers show DKIM fail or misalignment | | DMARC too weak or broken | Some providers accept mail, others spam it | DMARC reports show fails; policy may be p=none with no alignment plan | | Bad sender reputation | New domain or sudden volume spike causes filtering | High spam placement despite valid auth; low engagement; new IP/domain history | | Broken links or redirects | Email body looks normal but click tracking lands on odd URLs | Test all links through final redirect chain; watch for Cloudflare or app redirect loops | | Content triggers + low trust | Overuse of hype language, images only, too many CTA links | Spam tests score poorly; Gmail tabs into Promotions consistently |

For an AI chatbot product, I also watch for trust issues caused by automation. If your onboarding emails mention "instant AI", "secret system", "guaranteed results", or push too many links at once, inbox providers may not reject them outright but they will often downgrade them.

The Fix Plan

I would fix this in a controlled order so we do not break signup flows while trying to improve deliverability.

1. Lock down authentication first.

• Add one SPF record only.
• Add DKIM exactly as ConvertKit provides it.
• Publish a DMARC record with reporting enabled.
• Make sure the visible From address matches the authenticated sending domain.

2. Remove conflicting mail records.

• Delete old ESP includes from SPF if they are no longer used.
• Remove stale DKIM selectors from previous tools.
• Check there is only one active mail path per sending domain.

3. Move to a clean sending subdomain if needed.

• I usually recommend something like `mail.yourdomain.com` for marketing mail.
• Keep product-critical transactional mail separate from campaigns if possible.
• This reduces blast radius if reputation drops again.

4. Clean up Cloudflare and redirects.

• Make sure important landing pages resolve over HTTPS with valid SSL.
• Avoid chains longer than one redirect where possible.
• Do not proxy email-related verification endpoints unless you know why you are doing it.

5. Simplify the message content.

• Use one clear CTA per email.
• Reduce image-heavy templates until deliverability improves.
• Replace aggressive subject lines with plain language that matches user intent.

6. Warm up volume carefully if this is a new sender identity.

• Start with engaged users first.
• Send smaller batches over 3 to 7 days instead of blasting everyone at once.
• Watch spam complaints daily.

7. Add monitoring before resending broadly.

• Set alerts for bounce spikes above 2 percent.
• Set alerts for complaint rates above 0.1 percent to 0.3 percent depending on provider thresholds and list size.
• Track open rate drops by provider.

8. Re-test with seed inboxes before full rollout. ```text From: hello@yourdomain.com SPF: pass DKIM: pass DMARC: pass Alignment: pass Links: clean HTTPS ```

My rule here is simple: do not touch copy until authentication and routing are correct. If you change subject lines first, you are treating a symptom instead of fixing the actual risk.

Regression Tests Before Redeploy

Before I ship this fix, I want proof that both delivery and user experience are stable.

• Send test emails to Gmail, Outlook, Yahoo, and Apple Mail accounts.
• Confirm inbox placement in at least 3 out of 4 providers before broad release.
• Check full headers for SPF pass, DKIM pass, and DMARC pass.
• Click every link in the message body and verify final destination over HTTPS with no redirect loop.
• Confirm unsubscribe works in one click and does not require login friction that hurts compliance risk.
• Send from desktop and mobile preview modes to catch layout issues that affect trust scores visually.

Acceptance criteria I would use:

• Inbox placement improves from spam/promotions to primary/inbox for at least 2 major providers on seed accounts.
• Bounce rate stays under 2 percent after resend tests.
• Complaint rate stays under 0.1 percent during warmup sends.
• No broken links, mixed content warnings, or SSL errors on linked pages.
• Circle signup flow still works end to end after DNS changes.

If this were part of a production sprint, I would also run a small QA matrix:

• New subscriber path
• Existing subscriber re-entry path
• Mobile email rendering
• Dark mode rendering
• Unsubscribe path
• Reply-to behavior

Prevention

I would put guardrails around this so the problem does not come back two weeks later after another tool change.

• Keep one owner for DNS and email authentication changes. Most deliverability issues start when multiple people edit records without coordination.
• Add a change log for every mail-related update: sender domain, ESP switch, new subdomain, new tracking link pattern, template changes.
• Monitor SPF/DKIM/DMARC status weekly using external checks plus provider reports where available.
• Review copy before launch for trust signals:
• clear From name
• plain subject lines
• fewer links
• no misleading claims
• Separate transactional mail from marketing sequences so product reliability does not depend on campaign performance.
• Keep Cloudflare settings documented:
• SSL mode

clarity, proxied vs DNS-only records, cache rules, WAF exceptions if needed for verification endpoints

From a cyber security lens, this matters because spoofed sender identities create phishing risk as well as deliverability risk. If your authentication is weak, attackers can imitate your brand more easily and users will trust fewer messages from you overall.

When to Use Launch Ready

Use Launch Ready when you need me to fix this fast without turning your app into a science project.

This sprint fits best if:

• emails are landing in spam now,
• you just moved from prototype to live traffic,
• Circle and ConvertKit were stitched together quickly,
• you changed domains recently,
• you are about to spend money on ads but cannot trust delivery yet,
• you need production-safe fixes before more users hit signup.

What I need from you before starting:

• access to registrar or DNS provider,
• access to Cloudflare,
• access to ConvertKit admin,
• access to Circle admin,
• current sending domains and any old ESP details,
• examples of emails that landed in spam,
• list of key customer journeys that depend on email delivery.

My recommendation: do not keep patching this yourself if revenue depends on it. A bad deliverability setup can waste ad spend immediately because paid traffic lands into a broken onboarding funnel instead of a working product experience.

Delivery Map

References

1. Roadmap.sh API Security Best Practices: https://roadmap.sh/api-security-best-practices 2. Roadmap.sh Cyber Security: https://roadmap.sh/cyber-security 3. Roadmap.sh QA: https://roadmap.sh/qa 4. Google Email Sender Guidelines: https://support.google.com/a/answer/81126 5. ConvertKit Help Center on Deliverability and Authentication: https://help.convertkit.com/

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Take the next step

If this is a problem in your product right now, here is what to do next:

• [Use the free Cyprian tools](/tools) - estimate cost, score app risk, check launch readiness, or pick the right service sprint.

• [Book a discovery call](/contact) - I will tell you honestly whether you need a sprint or if you can DIY the next step.

*Written by Cyprian Tinashe Aarons - senior full-stack and AI engineer helping founders rescue, launch, automate, and scale AI-built products.*