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16.1. Live Lookup or webhook stopped working after upgrading to HelpSpot 5.8.7

Updated: 6 Oct 2026, 11:21 AM EDT

Applies to: HelpSpot 5.8.7 and later · HelpSpot Cloud and self-hosted · Live Lookup and automation-rule webhooks

What's happening

After upgrading HelpSpot, a Live Lookup source or an automation-rule webhook that previously worked has stopped. There is no error message:

• Live Lookup returns no matches for every customer, including ones it used to find.
• Automation-rule webhooks stop arriving at the receiving system. Nothing is written to the request history or the HelpSpot log.

Webhooks fired by triggers are not affected by this change and keep working as before.

Cause

As of HelpSpot 5.8.7, HelpSpot checks the TLS certificate on outbound HTTPS requests to Live Lookup sources and automation-rule webhook URLs. Earlier versions skipped certificate and hostname checks, so integrations with invalid certificates worked silently. When the check fails, HelpSpot gets no response from the integration and treats it as an empty result — which is why Live Lookup shows nothing rather than an error.

The integration's certificate is most likely one of the following:

• Self-signed
• Expired
• Issued for a different hostname than the one in the integration URL
• Signed by an internal certificate authority that the HelpSpot server doesn't trust

Confirm it's the certificate

Open the integration URL in a browser from the HelpSpot server, or from any machine on the same network. A certificate or security warning confirms the cause. If the page loads with no warning, the problem is somewhere else — check that the integration's server is reachable from HelpSpot at all.

How to fix it

Option 1: Fix the certificate (recommended)

Install a certificate from a trusted certificate authority on the integration's server, or add your internal CA to the HelpSpot server's trust store. This restores the integration without weakening security and is the only fix that works long-term.

Option 2: Add a temporary exception

1. Go to Admin > Settings > System and scroll to Outbound HTTP Requests.
2. In TLS Verification Exceptions, enter the integration's hostname. Use the exact hostname from the integration URL — no https:// or path. The port doesn't matter. Separate multiple hostnames with commas.
3. Click Save.
4. Run the Live Lookup again, or re-run the automation rule, to confirm it works.

If the entry doesn't match exactly, HelpSpot keeps verifying the request. An incorrect entry never weakens security — it just doesn't take effect.

Important: an exception disables certificate verification for the whole request, including any redirects to other hosts. Treat it as a stopgap and remove the exception once the certificate is fixed. See System for the full behavior of this setting.

Related articles

• System — TLS Verification Exceptions setting
• Live Lookup Configuration and Implementation
• HelpSpot 5.8.7 release notes