[GH-ISSUE #1021] handshakeFailed(NIOSSL.BoringSSLError.sslError([])) #1016

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opened 2026-03-03 19:23:48 +03:00 by kerem · 2 comments

kerem commented

2026-03-03 19:23:48 +03:00

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Originally created by @novitae on GitHub (Oct 9, 2021).
Original GitHub issue: https://github.com/ProxymanApp/Proxyman/issues/1021

Originally assigned to: @NghiaTranUIT on GitHub.

Proxyman version? (Ex. Proxyman 1.4.3)

2.33.0 (Free Version for now)

macOS Version? (Ex. mac 10.14)

macOs 11.1

Steps to reproduce

(Before doing this, configure your proxy, certificate and all on iPhone and Mac)
Connect the iPhone (it needs to have FaceTime enabled on it), open FaceTime, click "+" and search for a number or email that is connected with FaceTime (you can see if it is by going in contacts and check if the case "FaceTime" with the phone logo and camera logo shows up), then click enter (don't call it). The phone/email should look grey then switch to blue.
After having done this, you'll normally have 2 requests to https://query.ess.apple.com showed in Proxyman.
I enabled SSL proxying for this site (and for the other that might appear during the process).
The request is with a CONNECT method.

My problem

I get from this request a 999 Error code, here is the raw request :
CONNECT query.ess.apple.com:443 HTTP/1.1 Host: query.ess.apple.com:443
and in the response I get handshakeFailed(NIOSSL.BoringSSLError.sslError([])) (btw it seems in the [] we should have a detail from the error, I don't know why I don't get it but that might be because I'm in free version)

Screenshots (optional)

My questions

Since it is an apple domain, that might be very secure (but when we load a contact in apple contacts it shows all the requests details), I think it might be this https://www.raywenderlich.com/1484288-preventing-man-in-the-middle-attacks-in-ios-with-ssl-pinning, but if it is, how can I go threw that ??
And if it is something else, what is it ??

Thanks !

Originally created by @novitae on GitHub (Oct 9, 2021). Original GitHub issue: https://github.com/ProxymanApp/Proxyman/issues/1021 Originally assigned to: @NghiaTranUIT on GitHub. ### Proxyman version? (Ex. Proxyman 1.4.3) 2.33.0 (Free Version for now) ### macOS Version? (Ex. mac 10.14) macOs 11.1 ### Steps to reproduce (Before doing this, configure your proxy, certificate and all on iPhone and Mac) Connect the iPhone (it needs to have FaceTime enabled on it), open FaceTime, click "+" and search for a number or email that is connected with FaceTime (you can see if it is by going in contacts and check if the case "FaceTime" with the phone logo and camera logo shows up), then click enter (don't call it). The phone/email should look grey then switch to blue. After having done this, you'll normally have 2 requests to `https://query.ess.apple.com` showed in Proxyman. I enabled SSL proxying for this site (and for the other that might appear during the process). The request is with a CONNECT method. ### My problem I get from this request a 999 Error code, here is the raw request : `CONNECT query.ess.apple.com:443 HTTP/1.1 Host: query.ess.apple.com:443` and in the response I get `handshakeFailed(NIOSSL.BoringSSLError.sslError([]))` (btw it seems in the [] we should have a detail from the error, I don't know why I don't get it but that might be because I'm in free version) ### Screenshots (optional) <img width="1213" alt="Capture d’écran 2021-10-09 à 11 18 12" src="https://user-images.githubusercontent.com/85891169/136652367-d8f47cd0-5d49-4059-b2e8-c7393d0e1189.png"> ### My questions Since it is an apple domain, that might be very secure (but when we load a contact in apple contacts it shows all the requests details), I think it might be this [https://www.raywenderlich.com/1484288-preventing-man-in-the-middle-attacks-in-ios-with-ssl-pinning](https://www.raywenderlich.com/1484288-preventing-man-in-the-middle-attacks-in-ios-with-ssl-pinning), but if it is, how can I go threw that ?? And if it is something else, what is it ?? Thanks !

kerem closed this issue

2026-03-03 19:23:48 +03:00

kerem commented

2026-03-03 19:23:48 +03:00

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Owner

@NghiaTranUIT commented on GitHub (Oct 9, 2021):

Hey, if you're trying to intercept the FaceTime app, it highly is protected by SSL Pining to prevent the Mitm app to capture HTTPS traffic.

There is no way to bypass it unless you're are a Facetime developer, who has a pinned certificate.

@NghiaTranUIT commented on GitHub (Oct 9, 2021): Hey, if you're trying to intercept the FaceTime app, it highly is protected by SSL Pining to prevent the Mitm app to capture HTTPS traffic. There is no way to bypass it unless you're are a Facetime developer, who has a pinned certificate.

kerem commented

2026-03-03 19:23:49 +03:00

Author

Owner

@novitae commented on GitHub (Oct 9, 2021):

oh okay :( thanks for your answer !

@novitae commented on GitHub (Oct 9, 2021): oh okay :( thanks for your answer !