On fresh macOS install, `skip doctor` fails

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Steps to reproduce

Using UTM I installed a VM with a fresh copy of macOS Tahoe 26.2. (I created it with 16GB of RAM and 84 GB of disk; the default 64 wasn't enough for Xcode + iOS SDK, Android Studio + Android SDK, etc.)

VMs aren't allowed to use the App Store, so I then went to https://developer.apple.com/download/all/?q=Xcode and downloaded https://download.developer.apple.com/Developer_Tools/Xcode_26.2/Xcode_26.2_Apple_silicon.xip. I unxipped it it and copied Xcode.app into my Applications folder, without opening it.

Then, I ran /bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)" and then the post-install steps to add Homebrew to my path, and ran brew install skiptools/skip/skip. Then, I ran skip doctor --verbose. It failed.

Actual results

skip doctor --verbose failed.

Logs


executing command: /opt/homebrew/bin/skip version
Skip version 1.7.0
executing command: /usr/bin/sw_vers --productVersion
26.2
executing command: /usr/sbin/sysctl -n sysctl.proc_translated
0
executing command: /usr/bin/swift -version
Apple Swift version 6.2.3 (swiftlang-6.2.3.3.21 clang-1700.6.3.2)
Target: arm64-apple-macosx26.0
swift-driver version: 1.127.14.1 
executing command: /opt/homebrew/bin/swiftly --version
Could not load swiftly's configuration file at
/Users/dfabulich/.swiftly/config.json.
To begin using swiftly you can install it: '/opt/homebrew/bin/swiftly init'.
executing command: /usr/bin/xcodebuild -version
xcode-select: error: tool 'xcodebuild' requires Xcode, but active developer directory '/Library/Developer/CommandLineTools' is a command line tools instance
executing command: /opt/homebrew/bin/brew --version
Homebrew 5.0.13
executing command: /opt/homebrew/bin/gradle -version
------------------------------------------------------------
Gradle 9.3.1
------------------------------------------------------------
Build time:    2026-01-29 14:15:01 UTC
Revision:      44f4e8d3122ee6e7cbf5a248d7e20b4ca666bda3
Kotlin:        2.2.21
Groovy:        4.0.29
Ant:           Apache Ant(TM) version 1.10.15 compiled on August 25 2024
Launcher JVM:  25.0.2 (Homebrew 25.0.2)
Daemon JVM:    /opt/homebrew/Cellar/openjdk/25.0.2/libexec/openjdk.jdk/Contents/Home (no Daemon JVM specified, using current Java home)
OS:            Mac OS X 26.2 aarch64
executing command: /opt/homebrew/opt/java/bin/java -version
openjdk version "25.0.2" 2026-01-20
OpenJDK Runtime Environment Homebrew (build 25.0.2)
OpenJDK 64-Bit Server VM Homebrew (build 25.0.2, mixed mode, sharing)
executing command: /opt/homebrew/bin/adb version
Android Debug Bridge version 1.0.41
Version 36.0.2-14143358
Installed as /opt/homebrew/bin/adb
Running on Darwin 25.2.0 (arm64)

Skip Checkup output

Checkup output


dfabulich@Dans-Virtual-Machine ~ % skip checkup                                   
[✓] Skip version 1.7.0 (= 1.7.0)
[✓] macOS version 26.2 (> 13.5.0)
[✓] macOS architecture: ARM
[✓] Swift version 6.2.3 (> 5.9.0)
[✗] Swiftly version: error executing swiftly
[✗] Command failed with exit code 1
[✗] Skip 1.7.0 checkup failed with 2 errors

Start by reproducing skip doctor --verbose and skip checkup on the fresh macOS setup described, paying attention to the missing Swiftly configuration and the xcodebuild error. Trace the checkup entry point that reports Swiftly failures and determine the expected result for an uninitialized Swiftly installation; done means the reported failure matches the supported setup and the checkup output is correct.

Written by the indexing model from the issue text.

Description

Steps to reproduce

Actual results

Logs

Skip Checkup output

Contributor guide

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Assessment

On fresh macOS install, `skip doctor` fails

Description

Steps to reproduce

Actual results

Logs

Skip Checkup output

Contributor guide

First steps

Research direction

Assessment

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