iis - Chrome reports ERR_SPDY_INADEQUATE_TRANSPORT_SECURITY connecting to local web server over HTTPS

Summary

Chrome is reporting ERR_SPDY_INADEQUATE_TRANSPORT_SECURITY when I try and connect to my local web server over HTTPS. I am almost certain this problem has to do with my recent Windows 10 upgrade, but I don't know how to fix it.

What worked

Here's the chain of events, with me having Windows 8.1 Pro installed at the start:

1. Generated a self-signed certificate intended for use as a trusted root CA using the following command: makecert.exe -pe -ss Root -sr LocalMachine -n "CN=local, OU=development" -r -a sha512 -e 01/01/2020



2. Generated an application-specific certificate from the trusted root CA: makecert.exe -pe -ss My -sr LocalMachine -n "CN=myapp.local, OU=Development" -is Root -ir LocalMachine -in local -sp "Microsoft RSA SChannel Cryptographic Provider" -sy 12 -a sha512 -e 01/01/2020 -sky -eku 1.3.6.1.5.5.7.3.1


3. Added a HOSTS file entry for myapp.local that points to 127.0.0.1


4. Created an IIS 8.5 application that is bound to the myapp.local domain and listens for HTTPS requests only


5. Assigned the myapp.local certificate to the web site

With this setup, I had no trouble accessing my local web site from Chrome without any certificate or security warnings. The browser displayed the green padlock, as expected.

What doesn't work

Recently, I upgraded to Windows 10. I did not know at the time that Windows 10 ships with IIS 10, which supports HTTP/2. Now, when I try and access my local web sites with Chrome, I receive an ERR_SPDY_INADEQUATE_TRANSPORT_SECURITY error. I should note that the same request sent from Edge does not result in an error and does use HTTP/2 for the connection. A cursory Google search didn't turn up anything promising, except to hint that the problem might be that HTTP/2 or Chrome is strict about what ciphers it will accept in SSL certificates.

Thinking it may be an issue with enabled cipher suites in Windows (but not being an expert in such things), I downloaded the latest version of IIS Crypto. I clicked the Best Practices button, clicked Apply, and restarted my machine.

IIS Crypto reports these settings as "best practices":

• Enabled protocols: TLS 1.0, TLS 1.1, TLS 1.2


• Enabled ciphers: Triple DES 168, AES 128/128, AES 256/256


• Enabled hashes: MD5, SHA, SHA 256, SHA 384, SHA 512



• Enabled key exchanges: Diffie-Hellman, PKCS, ECDH



• SSL cipher suite order:

  
  
  

  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P521
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P256
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P521
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P284
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P256
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P521
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P284
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P256
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P521
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P284
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P256
  TLS_RSA_WITH_AES_256_GCM_SHA384
  TLS_RSA_WITH_AES_128_GCM_SHA256
  TLS_RSA_WITH_AES_256_CBC_SHA256
  TLS_RSA_WITH_AES_256_CBC_SHA
  TLS_RSA_WITH_AES_128_CBC_SHA256
  TLS_RSA_WITH_AES_128_CBC_SHA
  TLS_RSA_WITH_3DES_EDE_CBC_SHA

I'll also add that the browser application I'm developing does not need to be usable from Windows XP. I know there are some issues about Windows XP not supporting newer protocols.

Detailed information about the HTTPS negotiation

I decided to use Fiddler to intercept the HTTPS negotiation. Here's what Fiddler reported about the request:

Version: 3.3 (TLS/1.2)
Random: 6B 47 6D 2B BC AE 00 F1 1D 41 57 7C 46 DB 35 19 D7 EF A9 2B B1 D0 81 1D 35 0D 75 7E 4C 05 14 B0
"Time": 2/1/1993 9:53:15 AM
SessionID: 98 2F 00 00 15 E7 C5 70 12 70 CD A8 D5 C7 D4 4D ED D8 1F 42 F9 A8 2C E6 67 13 AD C0 47 C1 EA 04
Extensions: 
    server_name myapp.local
    extended_master_secret  empty
    SessionTicket   empty

    signature_algs  sha512_rsa, sha512_ecdsa, sha384_rsa, sha384_ecdsa, sha256_rsa, sha256_ecdsa, sha224_rsa, sha224_ecdsa, sha1_rsa, sha1_ecdsa
    status_request  OCSP - Implicit Responder
    NextProtocolNego    empty
    SignedCertTimestamp (RFC6962)   empty
    ALPN        http/1.1, spdy/3.1, h2-14, h2
    channel_id(GoogleDraft) empty
    ec_point_formats    uncompressed [0x0]
    elliptic_curves secp256r1 [0x17], secp384r1 [0x18]
Ciphers: 
    [C02B]  TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256

    [C02F]  TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256
    [009E]  TLS_DHE_RSA_WITH_AES_128_GCM_SHA256
    [CC14]  TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256
    [CC13]  TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256
    [CC15]  TLS_DHE_RSA_WITH_CHACHA20_POLY1305_SHA256
    [C00A]  TLS1_CK_ECDHE_ECDSA_WITH_AES_256_CBC_SHA
    [C014]  TLS1_CK_ECDHE_RSA_WITH_AES_256_CBC_SHA
    [0039]  TLS_DHE_RSA_WITH_AES_256_SHA
    [C009]  TLS1_CK_ECDHE_ECDSA_WITH_AES_128_CBC_SHA
    [C013]  TLS1_CK_ECDHE_RSA_WITH_AES_128_CBC_SHA

    [0033]  TLS_DHE_RSA_WITH_AES_128_SHA
    [009C]  TLS_RSA_WITH_AES_128_GCM_SHA256
    [0035]  TLS_RSA_AES_256_SHA
    [002F]  TLS_RSA_AES_128_SHA
    [000A]  SSL_RSA_WITH_3DES_EDE_SHA
    [00FF]  TLS_EMPTY_RENEGOTIATION_INFO_SCSV

Compression: 
    [00]    NO_COMPRESSION

and the response:

Version: 3.3 (TLS/1.2)
SessionID:  98 2F 00 00 15 E7 C5 70 12 70 CD A8 D5 C7 D4 4D ED D8 1F 42 F9 A8 2C E6 67 13 AD C0 47 C1 EA 04
Random:     55 C6 8D BF 78 72 88 41 34 BD B4 B8 DA ED D3 C6 20 5C 46 D6 5A 81 BD 6B FC 36 23 0B 15 21 5C F6
Cipher:     TLS_RSA_WITH_AES_128_GCM_SHA256 [0x009C]
CompressionSuite:   NO_COMPRESSION [0x00]
Extensions:
        ALPN        h2

        0x0017      empty
        renegotiation_info  00
        server_name empty

What's working

Based on Håkan Lindqvist's answer, and the very detailed and apparently-thoroughly-researched answer here, I reconfigured IIS Crypto with the following settings, which eliminated the Chrome error:

• Enabled protocols: TLS 1.0, TLS 2.0, TLS 3.0


• Enabled ciphers: AES 128/128, AES 256/256


• Enabled hashes: SHA, SHA 256, SHA 384, SHA 512


• Enabled key exchanges: Diffie-Hellman, PKCS, ECDH



• SSL cipher suite order:

  
  
  

  TLS_DHE_RSA_WITH_AES_256_GCM_SHA384
  TLS_DHE_RSA_WITH_AES_128_GCM_SHA256
  TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384_P521
  TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384_P384
  TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P521
  TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P384
  TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P256
  TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384_P521
  TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384_P384
  TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P521
  TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P384
  TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P256
  TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P521
  TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P384
  TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P256
  TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P521
  TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P384
  TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P256
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P521
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P256
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P521
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P384
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P256
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P521
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P384
  TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P256
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P521
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P384
  TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P256
  TLS_RSA_WITH_AES_256_GCM_SHA384
  TLS_RSA_WITH_AES_128_GCM_SHA256
  TLS_RSA_WITH_AES_256_CBC_SHA256
  TLS_RSA_WITH_AES_128_CBC_SHA256
  TLS_RSA_WITH_AES_256_CBC_SHA
  TLS_RSA_WITH_AES_128_CBC_SHA

Answer

Http/2 requirements as per https://http2.github.io/http2-spec/#rfc.section.9.2.2 :

9.2.2 TLS 1.2 Cipher Suites

A deployment of HTTP/2 over TLS 1.2 SHOULD NOT use any of the cipher suites that are listed in the cipher suite black list (Appendix A).

Endpoints MAY choose to generate a connection error (Section 5.4.1) of type INADEQUATE_SECURITY if one of the cipher suites from the black list is negotiated. A deployment that chooses to use a black-listed cipher suite risks triggering a connection error unless the set of potential peers is known to accept that cipher suite.

Implementations MUST NOT generate this error in reaction to the negotiation of a cipher suite that is not on the black list. Consequently, when clients offer a cipher suite that is not on the black list, they have to be prepared to use that cipher suite with HTTP/2.

The black list includes the cipher suite that TLS 1.2 makes mandatory, which means that TLS 1.2 deployments could have non-intersecting sets of permitted cipher suites. To avoid this problem causing TLS handshake failures, deployments of HTTP/2 that use TLS 1.2 MUST support TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 [TLS-ECDHE] with the P-256 elliptic curve [FIPS186].

Note that clients might advertise support of cipher suites that are on the black list in order to allow for connection to servers that do not support HTTP/2. This allows servers to select HTTP/1.1 with a cipher suite that is on the HTTP/2 black list. However, this can result in HTTP/2 being negotiated with a black-listed cipher suite if the application protocol and cipher suite are independently selected.

Your negotiated cipher TLS_RSA_WITH_AES_128_GCM_SHA256 is in the above mentioned (and linked) Http/2 blacklist.

I believe you will want to adjust your cipher suites (ordering?) to meet the above requirements. Maybe simply putting TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 with the NIST P-256 elliptic curve (identified as TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256_P256 on Windows) at the top of the list, or at least before anything included in the blacklist?