SSL Handshake Failed - iOS simulator

[yasinkafadar]

Description

I'm getting SSL Handshake Failed error. code=999. I've double checked iOS simulator settings. Proxyman cert has beed already installed and trusted. Proxyman version: 5.14.0

Steps to Reproduce

Current Behavior

Expected Behavior

Environment

Proxyman Version 5.14.0 (51400) | macOS: Version 15.3 (Build 24D60)

• macOS version: 15.3 (24D60)

[basselalesh]

seeing the same thing, going back to the previous Proxyman release fixes it

[NghiaTranUIT]

@yasinkafadar @basselalesh the latest update didn't change any iOS Simulator / Certificate logic. It should work.

Can you open Simulators -> Device Menu -> Erase all Contents and Settings… then, install the certificate to the simulator again?

I just tested with v5.14.0 and iOS 16.2 Simulator, it can decrypt HTTPS from Safari app.

[NghiaTranUIT]

@basselalesh can you verify both certificate are the same: Name, and expiry date:

• iOS Simulator -> Settings app -> General -> About -> Trust Settings
• Proxyman app -> Settings… -> Certificate Section

It should work if it's the same certificate

[NghiaTranUIT]

Tested with a basic SwiftUI, make a HTTPS requests to httpbin.org by using URLSession.

[basselalesh]

same certificate, erased settings, still doesn't work on the old version

I have the same one side by side with the old version which is intercepting the same responses no problem

[NghiaTranUIT]

Hm, it's odd. Can you launch a new iOS simulator and try again?

[basselalesh]

no luck

[yasinkafadar]

I had tried everything but not working :(

• Erase all content for simulators (tried most of them)
• Restart simulators
• Remove and add cert again and again
• It was working well just previous version

[yasinkafadar]

I removed one of them and then it starts working well again :)

[NghiaTranUIT]

@basselalesh how about your case?

Can you confirm that it's the same certificate?

---

@yasinkafadar do you use custom Root Certificate?

[NghiaTranUIT]

@yasinkafadar @basselalesh I found a bug.

You can fix it by going to the Proxyman -> Certificate menu -> Reset all Certificates. Then re-installing the certificate again.

The problem is: Your Keychain has 2 certificates, which are the same name, so Proxyman gets a wrong one.

[yasinkafadar]

Thank you for your support. When I removed one of them from keychain, It started working. So I couldn't test it as you described.

[TianyiZhao003]

Hi @NghiaTranUIT
I'm seeing the same issue (I'm on Version 5.14.0 (51400)) and I have tried all the troubleshooting provided above
I have only 1 certificate.

[TianyiZhao003]

Error from simulator:

error	16:34:39.037178-0800	com.apple.WebKit.Networking	StrictTrustEvaluate failed
error	16:34:39.046077-0800	com.apple.WebKit.Networking	boringssl_context_handle_fatal_alert(2165) [C1.1.1.1:2][0x138406680] write alert, level: fatal, description: certificate unknown
error	16:34:39.046099-0800	com.apple.WebKit.Networking	boringssl_context_error_print(2155) [C1.1.1.1:2][0x138406680] Error: 4318073472:error:1000007d:SSL routines:OPENSSL_internal:CERTIFICATE_VERIFY_FAILED:/Library/Caches/com.apple.xbs/Sources/boringssl_Sim/ssl/handshake.cc:419:
error	16:34:39.046729-0800	com.apple.WebKit.Networking	boringssl_session_handshake_incomplete(241) [C1.1.1.1:2][0x138406680] SSL library error
error	16:34:39.046751-0800	com.apple.WebKit.Networking	boringssl_session_handshake_error_print(44) [C1.1.1.1:2][0x138406680] Error: 4318073472:error:1000007d:SSL routines:OPENSSL_internal:CERTIFICATE_VERIFY_FAILED:/Library/Caches/com.apple.xbs/Sources/boringssl_Sim/ssl/handshake.cc:419:
error	16:34:39.046767-0800	com.apple.WebKit.Networking	nw_protocol_boringssl_handshake_negotiate_proceed(780) [C1.1.1.1:2][0x138406680] handshake failed at state 12288: not completed
error	16:34:39.046844-0800	com.apple.WebKit.Networking	nw_endpoint_flow_failed_with_error [C1.1.1.1 127.0.0.1:9090 in_progress socket-flow (satisfied (Path is satisfied), interface: lo0, proxy)] already failing, returning

[NghiaTranUIT]

@TianyiZhao003 Try the latest build v5.15.0.

Go to Certificate menu -> Reset all certificate -> Then, reinstalling it again on your Mac and simulator.

You can test it by visiting www.google.com on Safari app from your Simulator