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Created October 6, 2017 19:44
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Homebrew troubleshooting output on macOS 10.13
Overview

Homebrew does not recognize my Command Line Tools installation on macOS High Sierra (10.13). I had a working Homebrew installation before the upgrade. I'm getting the following any time I try to brew install:

Warning: Your Command Line Tools are too outdated. Update them from Software Update in the App Store.

I'm looking at the App Store right now and see that I have "Command Line Tools (macOS High Sierra version 10.13) for Xcode" installed. It's version 9.0.

brew doctor Output
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 and just ignore them. Thanks!

Warning: Your Command Line Tools are too outdated.
Update them from Software Update in the App Store.


Warning: Unbrewed header files were found in /usr/local/include.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae, and may need to be deleted.

Unexpected header files:
  /usr/local/include/tdbc.h
  /usr/local/include/mysqlStubs.h
  /usr/local/include/pqStubs.h
  /usr/local/include/tclOODecls.h
  /usr/local/include/itclTclIntStubsFcn.h
  /usr/local/include/itclIntDecls.h
  /usr/local/include/tcl.h
  /usr/local/include/itclMigrate2TclCore.h
  /usr/local/include/itcl.h
  /usr/local/include/tclThread.h
  /usr/local/include/tdbcInt.h
  /usr/local/include/tdbcDecls.h
  /usr/local/include/tclOO.h
  /usr/local/include/itcl2TclOO.h
  /usr/local/include/tk.h
  /usr/local/include/odbcStubs.h
  /usr/local/include/fakepq.h
  /usr/local/include/itclInt.h
  /usr/local/include/tkPlatDecls.h
  /usr/local/include/tclTomMathDecls.h
  /usr/local/include/tclTomMath.h
  /usr/local/include/fakemysql.h
  /usr/local/include/tclDecls.h
  /usr/local/include/tkDecls.h
  /usr/local/include/fakesql.h
  /usr/local/include/itclDecls.h
  /usr/local/include/tclPlatDecls.h

Warning: Some installed formula are missing dependencies.
You should `brew install` the missing dependencies:
  brew install openssl@1.1

Run `brew missing` for more details.

I think those header files are related to psycopg2 or similar. Not sure about the Tk/Tcl stuff. I have gone through and removed as many issues as I could. Without being able to do brew install, I can't take care of the openssl dependency.

brew config Output
HOMEBREW_VERSION: 1.3.4
ORIGIN: https://github.com/Homebrew/brew
HEAD: ac8b58537fe3dd71098a43afcc6a1785dcde1d39
Last commit: 11 days ago
Core tap ORIGIN: https://github.com/Homebrew/homebrew-core
Core tap HEAD: 0fdbc64e53a2b1e178093762742a0f8316aa9f2d
Core tap last commit: 3 hours ago
HOMEBREW_PREFIX: /usr/local
HOMEBREW_REPOSITORY: /usr/local/Homebrew
HOMEBREW_CELLAR: /usr/local/Cellar
HOMEBREW_BOTTLE_DOMAIN: https://homebrew.bintray.com
CPU: quad-core 64-bit broadwell
Homebrew Ruby: 2.3.3 => /System/Library/Frameworks/Ruby.framework/Versions/2.3/usr/bin/ruby
Clang: 9.0 build 900
Git: 2.12.2 => /usr/local/bin/git
Perl: /usr/bin/perl
Python: /usr/bin/python
Ruby: /usr/bin/ruby => /System/Library/Frameworks/Ruby.framework/Versions/2.3/usr/bin/ruby
Java: N/A
macOS: 10.13-x86_64
Xcode: N/A
CLT: (null)
X11: 2.7.11 => /opt/X11

The CLT: (null) is the troubling portion, as I have the CLT installed:

$ xcode-select -p
/Library/Developer/CommandLineTools
$ ll /Library/Developer/CommandLineTools/
total 0
drwxr-xr-x  5 root  admin  160 Sep  2 11:36 Library
drwxr-xr-x  4 root  wheel  128 Oct  6 15:01 SDKs
drwxr-xr-x  7 root  admin  224 Sep  2 11:36 usr

There are many executables in /Library/Developer/CommandLineTools/usr/bin/, most with root:admin and 755 perms. However, there are a few that are more restrictive:

$ find /Library/Developer/CommandLineTools/usr/bin/ -perm 700
/Library/Developer/CommandLineTools/usr/bin//gcov
/Library/Developer/CommandLineTools/usr/bin//g++
/Library/Developer/CommandLineTools/usr/bin//c++
/Library/Developer/CommandLineTools/usr/bin//git-receive-pack
/Library/Developer/CommandLineTools/usr/bin//objdump
/Library/Developer/CommandLineTools/usr/bin//git-upload-archive
/Library/Developer/CommandLineTools/usr/bin//dsymutil
/Library/Developer/CommandLineTools/usr/bin//otool
/Library/Developer/CommandLineTools/usr/bin//nm
/Library/Developer/CommandLineTools/usr/bin//clang++
/Library/Developer/CommandLineTools/usr/bin//swiftc
/Library/Developer/CommandLineTools/usr/bin//cc
/Library/Developer/CommandLineTools/usr/bin//size
/Library/Developer/CommandLineTools/usr/bin//ranlib
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