in arm64 macs, the sqlsrv drivers are failing to link to the openssl libraries

[triankar]

Over the last 10 days I have tried literally everything on the internet, trying to get my new M4 MBP to connect to some MSSQL servers ranging from 2016 to 2022.
I'm running an M4 Max machine with the latest macOS Tahoe 26.1. My previous dev machine is a 2019 i9 MBP, where everything was running smoothly until I did the absolutely stupidest ever mistake* of upgrading all homebrew packages. "oooh, 57 packages are out of date, let's upgrade things"! 🤡 Now nothing works there as well.

The homebrew method was obviously the first thing I tried on my new machine. I followed all the usual guides at learn.microsoft.com in order to install apache2, php and sqlsrv + pdo_sqlsrv packages and everything else the guide recommends.

I started off by installing the latest packages of each. php@8.5, msodbcsql18, openssl3 etc. And I could not connect.
Then I came to read that the latest packages DON'T work, so I tried installing lesser and lesser versions, going down to php@8.2 and msodbcsql13, among other things. Obviously unlinking and relinking everything along the way. And I was very careful about keeping everything under /opt/homebrew/etc/ in check.

Again, nothing worked.

I came to understand that it is mostly due to TLS handshakes failing between my macOS machine and the server(s), but there is nothing that will make them work. And believe me I tried every hint under the -sun- web!

Then I tried the "ditch arm64, install everything x86" path, and again NOTHING works.

Maybe I'm a little rusty with my Unix shell days and [configure/make/make install], but has ANYBODY had ANY luck connecting to an SQL server from PHP in an arm64 Mac???

*yes, that's a terrible habit: I see something that says "a new version of XYZ is there" and I immediately hit "update"

[triankar]

To help others narrow down the issue, I've gotten so far (with the help of Google Gemini) as to narrow things down to that "the Microsoft ODBC Driver 17 installer (even via Homebrew) is fundamentally failing to link to your OpenSSL 3.x library on your ARM64 system, and the driver is unusable for encrypted connections."

The last steps I did were:
otool -L /opt/homebrew/lib/libmsodbcsql.17.dylib | grep ssl
This returned nothing.
Then
brew remove msodbcsql17
export LDFLAGS="-L/opt/homebrew/opt/openssl@3/lib"
export CPPFLAGS="-I/opt/homebrew/opt/openssl@3/include"
brew install msodbcsql17

And then ran these two, which both produced no results:
otool -L /opt/homebrew/opt/msodbcsql17/lib/libmsodbcsql.17.dylib | grep ssl
otool -L /opt/homebrew/lib/libmsodbcsql.17.dylib | grep ssl

I hope this helps the dev team in MS to solve things

[David-Engel]

I don't have a Mac to play with so I can't replicate your scenario, but some things to keep in mind:

• The PHP driver only supports x64, so your "install everything x86" efforts should be on the right track.
• Stick to PHP 8.3 for now (or 8.1 or 8.2). The PHP driver doesn't yet support PHP 8.4+.
• Start with just getting the ODBC Driver to work. Use mssql-tools/mssql-tools18 and sqlcmd to verify (recommend 18, but 17 should also work).
• Your output/commands tells me that you are using ARM64 Homebrew (/opt/homebrew paths), which isn't going to work (see first bullet point). Homebrew running Rosetta 2 / x64 emulation will be under /usr/local. Make sure to start your terminal in emulation mode (arch -x86_64 /bin/zsh) when installing homebrew.

[triankar]

ok, I finally solved it. The problem is that macOS is very insistent in using the openssl@3 libraries.

Quick instructions:
DO NOT install anything using the arm64 version of homebrew. Do EVERYTHING using the x86 version. So, your very first step is
arch -x86_64 zsh

After that, do everything under this microsoft guide, completely ignoring any pointers to the Apple Silicon versions of the commands. You will need to stick to php@8.2 and openssl@1.1 (at least now - Dec/2025).

The things I do remember installing with brew are these at least: openssl@1.1, apache2, php@8.2, unixodbc, freetds.

Then the last bit is you need to check this:
ls -l /usr/local/opt/openssl/lib
If you see things pointing to openssl@3, you will need to
brew unlink openssl@3
brew link --force openssl@1
though these won't exactly solve the issue. You need one last step. From a root shell
cd /usr/local/opt/openssl/lib
ln -s openssl@1.1 openssl
And now if you run the previous ls -l command you need to see things pointing to @1.1 versions.

Only then will you stop getting the 0x2746 error.

I hope this helps some poor soul out there who's spent hours or even days in frustration getting those drivers to work!