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Cade's Dotfiles

OpenSSH upgrade fails with `inreplace failed ... sshd_config`

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Source: Troubleshooting reference

Symptom: OpenSSH finishes make install, then Homebrew aborts while replacing its Cellar prefix in the persistent configuration:

Error: inreplace failed
.../brew/etc/ssh/sshd_config:
  expected replacement of ".../Cellar/openssh/<version>" with ".../opt/openssh"

Root cause: Homebrew preserves files under etc across upgrades. After the first install, sshd_config already contains opt/openssh; a later install has no Cellar path left to replace, but the formula treats that valid no-op as an error.

Fix: install/patch-homebrew-openssh.sh guards the replacement with a content check. It leaves an already-normalized configuration untouched, while the formula’s test still rejects any Cellar path that remains.