From 41132b72db599dffcb3c17d84f27517ef89c6c4b Mon Sep 17 00:00:00 2001
From: Paul Medynski <31868385+paulmedynski@users.noreply.github.com>
Date: Mon, 15 Jun 2026 11:52:50 -0300
Subject: [PATCH 1/2] Fix macOS CI: trust microsoft/mssql-release tap for
 Homebrew 5.2+

Homebrew 5.2.0 made untrusted-tap enforcement the default. After
'brew update' pulls in the new version, 'brew install mssql-tools18'
is refused because the microsoft/mssql-release tap is untrusted.

This caused sqlcmd to never be installed (exit code 127), so the
SQL Server connectivity check looped for 72 attempts and failed.

Add 'brew trust microsoft/mssql-release' after tapping and before
'brew update' to explicitly trust the Microsoft tap.
---
 .../common/templates/steps/configure-sql-server-macos-step.yml   | 1 +
 1 file changed, 1 insertion(+)

diff --git a/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml b/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml
index a989bf19bf..95d3ac7b7a 100644
--- a/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml
+++ b/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml
@@ -33,6 +33,7 @@ steps:
       brew install colima
       brew install docker
       brew tap microsoft/mssql-release https://github.com/Microsoft/homebrew-mssql-release
+      brew trust microsoft/mssql-release
       brew update
       HOMEBREW_ACCEPT_EULA=Y brew install mssql-tools18
 

From 5c479a5eb09b267c0f39431f26a4e0c0e94474c2 Mon Sep 17 00:00:00 2001
From: Paul Medynski <31868385+paulmedynski@users.noreply.github.com>
Date: Mon, 15 Jun 2026 12:23:51 -0300
Subject: [PATCH 2/2] Address PR #4363 review feedback

- Move 'brew trust' after 'brew update' so it works even when the
  runner image starts with a Homebrew version older than 5.2.
- Add a fail-fast check after 'brew install mssql-tools18' to
  immediately abort with a clear error if sqlcmd is not on PATH,
  avoiding the 6-minute timeout loop.
---
 .../steps/configure-sql-server-macos-step.yml        | 12 +++++++++++-
 1 file changed, 11 insertions(+), 1 deletion(-)

diff --git a/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml b/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml
index 95d3ac7b7a..6e1541f939 100644
--- a/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml
+++ b/eng/pipelines/common/templates/steps/configure-sql-server-macos-step.yml
@@ -33,10 +33,20 @@ steps:
       brew install colima
       brew install docker
       brew tap microsoft/mssql-release https://github.com/Microsoft/homebrew-mssql-release
-      brew trust microsoft/mssql-release
       brew update
+      # Homebrew 5.2+ requires explicit trust for third-party taps.  Run this
+      # after 'brew update' so the trust command is available even if the runner
+      # image shipped an older Homebrew version.
+      brew trust microsoft/mssql-release
       HOMEBREW_ACCEPT_EULA=Y brew install mssql-tools18
 
+      # Fail fast if sqlcmd was not installed (e.g. tap-trust or formula error).
+      # Without this check the script would loop for ~6 minutes trying to connect.
+      if ! command -v sqlcmd &>/dev/null; then
+        echo "ERROR: sqlcmd is not on PATH after brew install. Check the mssql-tools18 installation above."
+        exit 1
+      fi
+
       # Start Colima with Virtualization.framework for x86_64 binary translation
       # on Apple Silicon.  Rosetta/binfmt emulation is enabled by default in
       # Colima >= 0.8 when using --vm-type vz, which is dramatically faster than