Make Evaluations Easier with Pre-Flight Check Tool - Active Deal Blocked

Active deal blocker
Large insurance customer has been trying to evaluate Duo AI for 2+ months and STILL cannot get it working. This is actively blocking their POC. Right now, they are trying to adopt Duo Core into their environment to eventually replace barebones CoPilot and wanting to move on to phase 2 of evaluating Duo Agent Platform in Jan 2026.

Current Status:

  • Both websockets AND gRPC failing due to Zscaler proxy with SSL inspection
  • Customer network team has allowed domains, HTTP/2, but SSL inspection is breaking bidirectional connections
  • Support ticket open since October 17 - still no resolution
  • Customer has SA + Support engaged but we're stuck

Root Cause: Enterprise proxy SSL inspection breaks websocket upgrades and gRPC streams. Our product doesn't detect this or provide actionable guidance.

Customer has indicated that Github has a diagnostic tool in gives actionable guidance , around security and network configuratin and access, to get CoPilot up and running. We need a similar tool.


What We Need to Unblock Future Evaluations:
:rotating_light: Pre-Flight Check Tool (CRITICAL)

  • Day 1 diagnostic that tests actual connectivity to our endpoints
  • Detects SSL inspection, proxy issues, protocol support
  • Gives customer specific "your network needs X, Y, Z" output
  • This would have saved 2 months of back-and-forth

:books: Enterprise Proxy Documentation

  • Step-by-step Zscaler/BlueCoat/Palo Alto configs
  • Exact SSL inspection bypass rules
  • What to ask their network team for

:zap: Smarter Error Handling

  • Detect SSL inspection → "Your proxy is intercepting certificates, websockets won't work. See docs..."
  • Stop showing generic "connection failed" errors

Business Impact:

  • 2+ months of evaluation time wasted
  • Large customer POC stalled, not able to adopt Duo Core + evaluation DAP
  • SA + Support hours consumed
  • Risk of lost deal

Can we prioritize the pre-flight diagnostic tool?

Support ticket: https://gitlab.zendesk.com/agent/tickets/664736

Account team: @sbailey1 @madkerr @rodneybowles @knelson42 @mcbgit @c.stapleton @cherryhan @brianwald

Edited by Ancil McBarnett