openssh - cannot connect to some hosts (system ssh can) / rebuild from source

[planetf1]

Output of brew config

HOMEBREW_VERSION: 4.4.20
ORIGIN: https://github.com/Homebrew/brew
HEAD: 47ef1a3b0b742a78be35c016df6a0279d6035ebb
Last commit: 19 hours ago
Branch: stable
Core tap JSON: 04 Feb 11:05 UTC
Core cask tap JSON: 04 Feb 11:05 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: []
HOMEBREW_DISPLAY: /private/tmp/com.apple.launchd.sGrf09RWJX/org.xquartz:0
HOMEBREW_MAKE_JOBS: 10
Homebrew Ruby: 3.3.7 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.3.7/bin/ruby
CPU: deca-core 64-bit arm_firestorm_icestorm
Clang: 16.0.0 build 1600
Git: 2.48.1 => /opt/homebrew/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 15.3-arm64
CLT: 16.2.0.0.1.1733547573
Xcode: 16.2
Rosetta 2: false

Output of brew doctor

Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: Some installed casks are deprecated or disabled.
You should find replacements for the following casks:
  authy
  microsoft-remote-desktop

Warning: Some installed kegs have no formulae!
This means they were either deleted or installed manually.
You should find replacements for the following formulae:
  python-pathspec
  python-typing-extensions

Warning: Some installed formulae are deprecated or disabled.
You should find replacements for the following formulae:
  libgit2@1.7
  node@18
  openssl@1.1
  pyyaml
  terraform

Description of issue

OpenSSH from homebrew seems to have a problem connecting to some hosts, not all, client is running macOS 15.3. The system ssh has no such problems. For example

ie OpenSSH_9.9p1, OpenSSL 3.4.0 22 Oct 2024 fails:

debug3: ssh_connect_direct: entering
debug1: Connecting to 192.168.100.163 [192.168.100.163] port 22.
debug3: set_sock_tos: set socket 3 IP_TOS 0x48
debug1: connect to address 192.168.100.163 port 22: No route to host
ssh: connect to host 192.168.100.163 port 22: No route to host

but OpenSSH_9.8p1, LibreSSL 3.3.6 fails:

debug3: ssh_connect_direct: entering
debug1: Connecting to 192.168.100.163 [192.168.100.163] port 22.
debug3: set_sock_tos: set socket 3 IP_TOS 0x48
debug1: Connection established.
debug1: identity file /Users/jonesn/OneDrive/keys/pi/keyssh type 0
debug1: identity file /Users/jonesn/OneDrive/keys/pi/keyssh-cert type -1
debug1: Local version string SSH-2.0-OpenSSH_9.8
debug1: Remote protocol version 2.0, remote software version OpenSSH_9.9 FreeBSD-openssh-portable-9.9.p1_1,1
debug1: compat_banner: match: OpenSSH_9.9 FreeBSD-openssh-portable-9.9.p1_1,1 pat OpenSSH* compat 0x04000000

The same is seen with some other hosts (all are on the same flat subnet 255.255.255.0), as well as with IPv6

Additionally, I tried building openssh from source (in case of a compile issue) but this failed:

brew install --build-from-source openssh
==> Downloading https://formulae.brew.sh/api/formula.jws.json
==> Downloading https://formulae.brew.sh/api/cask.jws.json
==> Fetching dependencies for openssh: libcbor and libfido2
==> Fetching libcbor
==> Downloading https://ghcr.io/v2/homebrew/core/libcbor/manifests/0.11.0
################################################################################################################ 100.0%
==> Downloading https://ghcr.io/v2/homebrew/core/libcbor/blobs/sha256:1316d2dd79be63a69f00cf06f50dc76fd24ad9e08552cff8a
################################################################################################################ 100.0%
==> Fetching libfido2
==> Downloading https://ghcr.io/v2/homebrew/core/libfido2/manifests/1.15.0
################################################################################################################ 100.0%
==> Downloading https://ghcr.io/v2/homebrew/core/libfido2/blobs/sha256:b07f0c07f5b2bc30b51b11ab15bb6424bc6f12c2d777af1c
################################################################################################################ 100.0%
==> Fetching openssh
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-core/1dec0239090bc2a029a30d15e93ece1a16530065/Formu
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/15d234d73c33f49c0247e2b0bd1b6694959d81bd6215a654e8b559b8eee48a46--openssh.rb
==> Downloading https://raw.githubusercontent.com/Homebrew/patches/1860b0a745f1fe726900974845d1b0dd3c3398d6/openssh/pat
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/95d698837964beb73f06395641d832d2426e0ade19e500e8f7d6722e021eec06--patch-sandbox-darwin.c-apple-sandbox-named-external.diff
==> Downloading https://raw.githubusercontent.com/Homebrew/formula-patches/aa6c71920318f97370d74f2303d6aea387fb68e4/ope
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/4b367cfd6a00f3f02964bf4d6147ab995fabaeb0d11d6a53f2b608f272b56503--patch-sshd.c-apple-sandbox-named-external.diff
==> Downloading https://raw.githubusercontent.com/apple-oss-distributions/OpenSSH/OpenSSH-268.100.4/com.openssh.sshd.sb
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/baa84afa74020f094e529cc17700218caff39c13c378ea1e59a3d53de54d0510--com.openssh.sshd.sb
==> Downloading https://cdn.openbsd.org/pub/OpenBSD/OpenSSH/portable/openssh-9.9p1.tar.gz
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/b671b4c8ee4ddea54a1e8ce9c9e1e09c48f7fcf0e3b1f92e234b74e5355e6472--openssh-9.9p1.tar.gz
==> Installing dependencies for openssh: libcbor and libfido2
==> Installing openssh dependency: libcbor
==> Downloading https://ghcr.io/v2/homebrew/core/libcbor/manifests/0.11.0
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/547a8f3a73e95b1a6ae76032004f514d926b4dbe82bab530cb3dd011c85c23ed--libcbor-0.11.0.bottle_manifest.json
==> Pouring libcbor--0.11.0.arm64_sequoia.bottle.tar.gz
🍺  /opt/homebrew/Cellar/libcbor/0.11.0: 34 files, 201.9KB
==> Installing openssh dependency: libfido2
==> Downloading https://ghcr.io/v2/homebrew/core/libfido2/manifests/1.15.0
Already downloaded: /Users/jonesn/Library/Caches/Homebrew/downloads/292955ce6f66d4d7d827690a78eeac2946aab6468af64c128d6083ee8658337d--libfido2-1.15.0.bottle_manifest.json
==> Pouring libfido2--1.15.0.arm64_sequoia.bottle.tar.gz
🍺  /opt/homebrew/Cellar/libfido2/1.15.0: 562 files, 1.3MB
==> Installing openssh
==> Patching
==> Applying patch-sandbox-darwin.c-apple-sandbox-named-external.diff
==> Applying patch-sshd.c-apple-sandbox-named-external.diff
==> ./configure --sysconfdir=/opt/homebrew/etc/ssh --with-ldns --with-libedit --with-kerberos5 --with-pam --with-ssl-di
==> make
==> make install
Error: inreplace failed
/opt/homebrew/etc/ssh/sshd_config:
  expected replacement of "/opt/homebrew/Cellar/openssh/9.9p1" with "/opt/homebrew/opt/openssh"

READ THIS: https://docs.brew.sh/Troubleshooting

Any ideas of things to check? Or how to get the local build working (other than go back to original sources & create a custom build)

[SMillerDev]

Did you report this to the OpenSSH project? They're much better equipped to help you debug this.

[imboli]

Backup and remove the directory /opt/homebrew/etc/ssh/.

[planetf1]

~macos 15.3.1 had some wierd ssh issues. Since then I've applied OS updates (and openssh is also up to date) and not seeing issues. therefore closing.