I asked this over in Networking and was pointed here as a more likely plae to find an answer.
We see that the TLS handshake for Safari connections is sending different sets of ciphers in the CLIENT_HELLO message for connections to the same URL from the same device.
Sometimes the set of cipher suites doesn't include the ciphers accepted by the back end server and sometimes it does. This shows up to the user as intermittent connection failures.
So why isn't the handshake always sending the same list of cipher suites? I can sort of imagine that the system is doing some arcane calculation about what cipher suites to send in the CLIENT_HELLO for a particular URL, but I'd expect the result to always be the same for that URL.
There's a post in the community forums about a similar (but not quite the same) issue which didn't get any real answer: Safari sends different list of supported ciphers for two URLs on the same domain
In that case it was different URLs, in this case it's the exact same URL.
We're seeing this on iOS 12, and it appears to also be happening on iOS 11. Haven't checked earlier versions yet. It happens on both iPad and iPhone.
For example, here are two sets of cipher suites for two sequential connections to the same back end server. These are sequential connections (no other traffic from the device between these two connections). Both handshakes succeeded in this example, so why different cipher suites?:
Cipher Suites (14 suites)
Cipher Suite: Unknown (0x5a5a)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca9)
Cipher Suite: TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca8)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 (0xc02b)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 (0xc02c)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (0xc030)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA (0xc013)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (0xc014)
Cipher Suite: TLS_RSA_WITH_AES_128_GCM_SHA256 (0x009c)
Cipher Suite: TLS_RSA_WITH_AES_256_GCM_SHA384 (0x009d)
Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA (0x002f)
Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA (0x0035)
Cipher Suite: TLS_RSA_WITH_3DES_EDE_CBC_SHA (0x000a)
Cipher Suites (22 suites)
Cipher Suite: TLS_EMPTY_RENEGOTIATION_INFO_SCSV (0x00ff)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 (0xc02c)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 (0xc02b)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384 (0xc024)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256 (0xc023)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA (0xc00a)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA (0xc009)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_3DES_EDE_CBC_SHA (0xc008)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (0xc030)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 (0xc028)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256 (0xc027)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (0xc014)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA (0xc013)
Cipher Suite: TLS_ECDHE_RSA_WITH_3DES_EDE_CBC_SHA (0xc012)
Cipher Suite: TLS_RSA_WITH_AES_256_GCM_SHA384 (0x009d)
Cipher Suite: TLS_RSA_WITH_AES_128_GCM_SHA256 (0x009c)
Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA256 (0x003d)
Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA256 (0x003c)
Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA (0x0035)
Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA (0x002f)
Cipher Suite: TLS_RSA_WITH_3DES_EDE_CBC_SHA (0x000a)
