diff --git a/.gitlab/ci/test.gitlab-ci.yml b/.gitlab/ci/test.gitlab-ci.yml
index 0608f1504a9eba2b4b23157e949622d62a6b0f5b..bf7d10592c9b5872b73d5bfc2a95ba33c1545bb5 100644
--- a/.gitlab/ci/test.gitlab-ci.yml
+++ b/.gitlab/ci/test.gitlab-ci.yml
@@ -4,6 +4,15 @@
   stage: test
   needs: []
 
+.ruby-job:
+  image: "ruby:${RUBY_VERSION}"
+  before_script:
+    - gem install gitlab-sdk
+    - gem install sentry-ruby
+  parallel:
+    matrix:
+      - RUBY_VERSION: ["3.0", "3.1", "3.2"]
+
 docs-lint:
   extends:
     - .test-job
@@ -16,26 +25,19 @@ rubocop:
   extends:
     - .test-job
     - .rules:code-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   script:
     - make rubocop
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
 
 rspec:
   extends:
     - .test-job
     - .rules:code-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   variables:
     RSPEC_ARGS: "--format doc --format RspecJunitFormatter --out rspec.xml"
   script:
     - make rspec
-  cache:
-    key: "ruby-${RUBY_VERSION}-bundle"
-    paths:
-      - $BUNDLE_PATH
   artifacts:
     paths:
       - rspec.xml
@@ -44,27 +46,24 @@ rspec:
       coverage_report:
         coverage_format: cobertura
         path: coverage/coverage.xml
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
 
 shellcheck:
   extends:
     - .test-job
     - .rules:code-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   script:
     - apt-get update
     - make shellcheck
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
 
 checkmake:
   extends:
     - .test-job
     - .rules:code-changes
   image: registry.gitlab.com/gitlab-org/gitlab-development-kit/asdf-bootstrapped-verify:main
+  before_script:
+    - gem install gitlab-sdk
+    - gem install sentry-ruby
   script:
     - make checkmake
 
@@ -72,18 +71,15 @@ gdk-example-yml:
   extends:
     - .test-job
     - .rules:code-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   script:
     - make verify-gdk-example-yml
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
 
 asdf-combine:
   extends:
     - .test-job
     - .rules:code-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   artifacts:
     when: on_failure
     paths:
@@ -92,33 +88,24 @@ asdf-combine:
     - make verify-asdf-combine
   rules:
     - if: '$CI_PIPELINE_SOURCE == "schedule"'
-    - if: '$CI_MERGE_REQUEST_IID'
+    - if: "$CI_MERGE_REQUEST_IID"
       changes:
         - ".tool-versions*"
         - "support/asdf-combine"
         - "support/ci/verify-asdf-combine"
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
 
 makefile-config:
   extends:
     - .test-job
     - .rules:code-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   script:
     - support/ci/verify-makefile-config
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
 
 ruby-version:
   extends:
     - .test-job
     - .rules:ruby-version-changes
-  image: "ruby:${RUBY_VERSION}"
+    - .ruby-job
   script:
     - support/ruby-check-versions
-  parallel:
-    matrix:
-      - RUBY_VERSION: ['3.0', '3.1', '3.2']
diff --git a/Gemfile b/Gemfile
index e5b92b598cd972a02363442d9b579ccc071cdbe7..52f1849cda38d6377480d4c69580f46767f8c2ad 100644
--- a/Gemfile
+++ b/Gemfile
@@ -23,3 +23,6 @@ group :development, :test, :danger do
   gem 'gitlab-dangerfiles', '~> 3.10.0', require: false
   gem 'resolv', '~> 0.2.2', require: false
 end
+
+gem 'gitlab-sdk', '~> 0.2.2'
+gem 'sentry-ruby', '~> 5.11'
diff --git a/Gemfile.lock b/Gemfile.lock
index ab310f477a64934e272f39f2c5dde7e9f501fa20..55d8186800b9e29b06093a8a6de2514a16186c41 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -54,6 +54,10 @@ GEM
       danger (>= 8.4.5)
       danger-gitlab (>= 8.0.0)
       rake
+    gitlab-sdk (0.2.2)
+      activesupport (>= 5.2.0)
+      rake (~> 13.0)
+      snowplow-tracker (~> 0.8.0)
     gitlab-styles (10.0.0)
       rubocop (~> 1.43.0)
       rubocop-graphql (~> 0.18)
@@ -151,6 +155,8 @@ GEM
     sawyer (0.9.2)
       addressable (>= 2.3.5)
       faraday (>= 0.17.3, < 3)
+    sentry-ruby (5.11.0)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
     simplecov (0.21.2)
       docile (~> 1.1)
       simplecov-html (~> 0.11)
@@ -160,6 +166,7 @@ GEM
       simplecov (~> 0.19)
     simplecov-html (0.12.3)
     simplecov_json_formatter (0.1.4)
+    snowplow-tracker (0.8.0)
     terminal-table (3.0.2)
       unicode-display_width (>= 1.1.1, < 3)
     tzinfo (2.0.6)
@@ -172,6 +179,7 @@ PLATFORMS
 
 DEPENDENCIES
   gitlab-dangerfiles (~> 3.10.0)
+  gitlab-sdk (~> 0.2.2)
   gitlab-styles (~> 10.0.0)
   irb (~> 1.7.0)
   lefthook (~> 1.4.1)
@@ -182,6 +190,7 @@ DEPENDENCIES
   rspec_junit_formatter (~> 0.6.0)
   rubocop
   rubocop-rake (~> 0.6.0)
+  sentry-ruby (~> 5.11)
   simplecov-cobertura (~> 2.1.0)
   yard (~> 0.9.34)
 
diff --git a/HELP b/HELP
index 74a026582ab86dc10a498674f6e10fa2cc28086f..1518c99587a1bfa6a581c76a312880263dc74cfc 100644
--- a/HELP
+++ b/HELP
@@ -40,6 +40,8 @@ Manage GDK:
   gdk diff-config                                   # Print difference between current
                                                     #  and new configuration values
 
+  gdk telemetry                                     # Opt in or out of error tracking and analytic data collection
+
   gdk reset-data                                    # Back up and create fresh git repository, PostgreSQL
                                                     #  data and Rails upload directory
   gdk reset-praefect-data                           # Back up and create fresh Praefect PostgreSQL data
diff --git a/data/announcements/0007_telemetry.yml b/data/announcements/0007_telemetry.yml
new file mode 100644
index 0000000000000000000000000000000000000000..e3316a74c65b34a26d5132d921f6d612d25ecd20
--- /dev/null
+++ b/data/announcements/0007_telemetry.yml
@@ -0,0 +1,10 @@
+---
+header: GDK now supports error tracking and analytic data
+body: |
+  To improve GDK, GitLab would like to collect basic error and usage
+  data to see how GDK is used and how it is performing.
+  
+  You can opt in to send error and analytic data to GitLab by running `gdk telemetry`.
+
+  For more details, see
+  https://gitlab.com/groups/gitlab-org/-/epics/9255.
diff --git a/doc/gdk_commands.md b/doc/gdk_commands.md
index 40c7489c57ec4b45ec4f90d4c08827c97bccd6c8..0dfa6891f9e289ca81f51bc38fee52fc82089b0e 100644
--- a/doc/gdk_commands.md
+++ b/doc/gdk_commands.md
@@ -292,3 +292,15 @@ basic workflow in the repository.
 
 The reports are stored in `<gdk-root>/sitespeed-result` as `<branch>_YYYY-MM-DD-HH-MM-SS`. This
 requires Docker installed and running.
+
+## Toggle Telemetry
+
+```shell
+gdk telemetry
+```
+
+Use the `gdk telemetry` command to enable and disable GDK telemetry. GDK telemetry can be:
+
+- Enabled, and associated with a GitLab username.
+- Enabled anonymously.
+- Disabled.
diff --git a/gdk.example.yml b/gdk.example.yml
index 9baeb86c067b4b4085573a0b32fd0963119f03d1..aee8ea969feb451065a8ecfca79ec3d3b3dbc642 100644
--- a/gdk.example.yml
+++ b/gdk.example.yml
@@ -428,6 +428,9 @@ sshd:
   use_gitlab_sshd: true
   user: git
   web_listen: 127.0.0.1:9122
+telemetry:
+  enabled: false
+  username: ''
 tracer:
   build_tags: tracer_static tracer_static_jaeger
   jaeger:
diff --git a/gem/gitlab-development-kit.gemspec b/gem/gitlab-development-kit.gemspec
index c1874d2a3734290d7c3e9342f75ad71672f19e9f..1441ee74002672e0316e9cf67b851fedc85f8410 100644
--- a/gem/gitlab-development-kit.gemspec
+++ b/gem/gitlab-development-kit.gemspec
@@ -17,6 +17,8 @@ Gem::Specification.new do |spec|
   spec.executables   = ['gdk']
 
   spec.required_ruby_version = '>= 3.0.5'
+  spec.add_dependency 'gitlab-sdk', '~> 0.2.2'
   spec.add_dependency 'rake', '~> 13.0'
+  spec.add_dependency 'sentry-ruby', '~> 5.11'
   spec.metadata['rubygems_mfa_required'] = 'true'
 end
diff --git a/lib/gdk.rb b/lib/gdk.rb
index 8e79ee3052fdbd359743637fc139c277d11cb757..2573ccef37b452f1acefa7ac77e48216a6b9004f 100644
--- a/lib/gdk.rb
+++ b/lib/gdk.rb
@@ -13,6 +13,7 @@
 
 autoload :Asdf, 'asdf'
 autoload :Shellout, 'shellout'
+autoload :Telemetry, 'telemetry'
 
 # GitLab Development Kit
 module GDK
@@ -104,7 +105,7 @@ def self.main
     validate_yaml! unless SUBCOMMANDS_NOT_REQUIRING_YAML_VALIDATION.include?(subcommand)
 
     if ::GDK::Command::COMMANDS.key?(subcommand)
-      exit(::GDK::Command::COMMANDS[subcommand].call.new.run(ARGV))
+      exit(run(subcommand))
     else
       suggestions = DidYouMean::SpellChecker.new(dictionary: ::GDK::Command::COMMANDS.keys).correct(subcommand)
       message = ["#{subcommand} is not a GDK command"]
@@ -151,15 +152,19 @@ def self.template_root
   def self.make(*targets, env: {})
     sh = Shellout.new(MAKE, targets, chdir: GDK.root, env: env)
     sh.stream
-    sh.success?
+    sh
   end
 
   def self.validate_yaml!
     config.validate!
     nil
   rescue StandardError => e
-    GDK::Output.error("Your gdk.yml is invalid.\n\n")
+    GDK::Output.error("Your gdk.yml is invalid.\n\n", e)
     GDK::Output.puts(e.message, stderr: true)
     abort('')
   end
+
+  def self.run(subcommand)
+    Telemetry.with_telemetry(subcommand) { ::GDK::Command::COMMANDS[subcommand].call.new.run(ARGV) }
+  end
 end
diff --git a/lib/gdk/command.rb b/lib/gdk/command.rb
index 8df3cd012cdcca8648b0670a3969432d20af6733..1c21fa494cac16ae2371028f71466d9d3026094a 100644
--- a/lib/gdk/command.rb
+++ b/lib/gdk/command.rb
@@ -18,6 +18,7 @@ module Command
     autoload :MeasureUrl, 'gdk/command/measure_url'
     autoload :MeasureWorkflow, 'gdk/command/measure_workflow'
     autoload :Open, 'gdk/command/open'
+    autoload :Telemetry, 'gdk/command/telemetry'
     autoload :Pristine, 'gdk/command/pristine'
     autoload :Psql, 'gdk/command/psql'
     autoload :PsqlGeo, 'gdk/command/psql_geo'
@@ -57,6 +58,7 @@ module Command
       'measure' => -> { GDK::Command::MeasureUrl },
       'measure-workflow' => -> { GDK::Command::MeasureWorkflow },
       'open' => -> { GDK::Command::Open },
+      'telemetry' => -> { GDK::Command::Telemetry },
       'psql' => -> { GDK::Command::Psql },
       'psql-geo' => -> { GDK::Command::PsqlGeo },
       'pristine' => -> { GDK::Command::Pristine },
diff --git a/lib/gdk/command/config.rb b/lib/gdk/command/config.rb
index 0218cf902db471bbea3d8f3eef1103717fe88a95..ebddc855ecc8877f214fcf33fcb9c804197b8806 100644
--- a/lib/gdk/command/config.rb
+++ b/lib/gdk/command/config.rb
@@ -42,7 +42,7 @@ def config_get(*name)
       rescue GDK::ConfigSettings::SettingUndefined
         GDK::Output.abort("Cannot get config for #{name.join('.')}")
       rescue GDK::ConfigSettings::UnsupportedConfiguration => e
-        GDK::Output.abort("#{e.message}.")
+        GDK::Output.abort("#{e.message}.", e)
       end
 
       def config_set(slug, value)
@@ -65,12 +65,12 @@ def config_set(slug, value)
         GDK::Output.info("Don't forget to run 'gdk reconfigure'.")
 
         true
-      rescue GDK::ConfigSettings::SettingUndefined
-        GDK::Output.abort("Cannot get config for '#{slug}'.")
+      rescue GDK::ConfigSettings::SettingUndefined => e
+        GDK::Output.abort("Cannot get config for '#{slug}'.", e)
       rescue TypeError => e
-        GDK::Output.abort(e.message)
+        GDK::Output.abort(e.message, e)
       rescue StandardError => e
-        GDK::Output.error(e.message)
+        GDK::Output.error(e.message, e)
         abort
       end
     end
diff --git a/lib/gdk/command/install.rb b/lib/gdk/command/install.rb
index 8e870fb4553c86a23c4ab0e02290b3a936b48e43..356bfb2c030df1c7f4ba5a54560f80a61ba50421 100644
--- a/lib/gdk/command/install.rb
+++ b/lib/gdk/command/install.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require_relative '../../telemetry'
+
 module GDK
   module Command
     # Handles `gdk install` command execution
@@ -8,14 +10,23 @@ module Command
     # - gitlab_repo=<url to repository> (defaults to: "https://gitlab.com/gitlab-org/gitlab")
     class Install < BaseCommand
       def run(args = [])
+        args.each do |arg|
+          next unless arg.start_with?('telemetry_user=')
+
+          username = arg.split('=').last
+          ::Telemetry.update_settings(username)
+
+          break
+        end
+
         result = GDK.make('install', *args)
 
-        unless result
-          GDK::Output.error('Failed to install.')
+        unless result.success?
+          GDK::Output.error('Failed to install.', result.stderr_str)
           display_help_message
         end
 
-        result
+        result.success?
       end
     end
   end
diff --git a/lib/gdk/command/pristine.rb b/lib/gdk/command/pristine.rb
index 6a83f9ae22b7dddd2ced41ac364796b0f92092bf..f960c63f0c0d81a4f14bfaacfa16043b489480b1 100644
--- a/lib/gdk/command/pristine.rb
+++ b/lib/gdk/command/pristine.rb
@@ -30,7 +30,7 @@ def run(_args = [])
 
         true
       rescue StandardError => e
-        GDK::Output.error("Failed to run 'gdk pristine' - #{e.message}.")
+        GDK::Output.error("Failed to run 'gdk pristine' - #{e.message}.", e)
         display_help_message
 
         false
diff --git a/lib/gdk/command/reconfigure.rb b/lib/gdk/command/reconfigure.rb
index cf3bf2ba51b1e20db849bd2785bb8b0edcd43113..c2875b37e125125e6b0e3b986faa4bdd61be7145 100644
--- a/lib/gdk/command/reconfigure.rb
+++ b/lib/gdk/command/reconfigure.rb
@@ -7,12 +7,12 @@ class Reconfigure < BaseCommand
       def run(_args = [])
         result = GDK.make('reconfigure')
 
-        unless result
-          GDK::Output.error('Failed to reconfigure.')
+        unless result.success?
+          GDK::Output.error('Failed to reconfigure.', result.stderr_str)
           display_help_message
         end
 
-        result
+        result.success?
       end
     end
   end
diff --git a/lib/gdk/command/reset_data.rb b/lib/gdk/command/reset_data.rb
index 45194970e6338f479108b63ad073758f13c90bd7..fc632264c7b6552c2cc490b33fd814f1a6423035 100644
--- a/lib/gdk/command/reset_data.rb
+++ b/lib/gdk/command/reset_data.rb
@@ -27,11 +27,13 @@ def stop_and_backup!
       end
 
       def reset_data!
-        if GDK.make('ensure-databases-setup', 'reconfigure')
+        result = GDK.make('ensure-databases-setup', 'reconfigure')
+
+        if result.success?
           GDK::Output.notice('Successfully reset data!')
           GDK::Command::Start.new.run
         else
-          GDK::Output.error('Failed to reset data.')
+          GDK::Output.error('Failed to reset data.', result.stderr_str)
           display_help_message
 
           false
@@ -61,7 +63,7 @@ def create_directory(directory)
 
         true
       rescue Errno::ENOENT => e
-        GDK::Output.error("Failed to create directory '#{directory}' - #{e}")
+        GDK::Output.error("Failed to create directory '#{directory}' - #{e}", e)
         false
       end
 
@@ -78,7 +80,7 @@ def backup_path(message, *path)
 
         true
       rescue SystemCallError => e
-        GDK::Output.error("Failed to rename path '#{path}' to '#{path_to_backup}/' - #{e}")
+        GDK::Output.error("Failed to rename path '#{path}' to '#{path_to_backup}/' - #{e}", e)
         false
       end
 
diff --git a/lib/gdk/command/telemetry.rb b/lib/gdk/command/telemetry.rb
new file mode 100644
index 0000000000000000000000000000000000000000..24941f5d1cc42d2b4cd538561bdd0bd754253bea
--- /dev/null
+++ b/lib/gdk/command/telemetry.rb
@@ -0,0 +1,34 @@
+# frozen_string_literal: true
+
+require_relative '../../telemetry'
+
+module GDK
+  module Command
+    class Telemetry < BaseCommand
+      def run(_ = [])
+        puts <<~TEXT
+          To improve GDK, GitLab would like to collect basic error and usage data. Please choose one of the following options:
+
+          - To send data to GitLab, enter your GitLab username.
+          - To send data to GitLab anonymously, leave blank.
+          - To avoid sending data to GitLab, enter a period ('.').
+        TEXT
+
+        username = $stdin.gets&.chomp
+        ::Telemetry.update_settings(username)
+
+        puts \
+          case username
+          when '.'
+            'Error tracking and analytic data will not be collected.'
+          when '', NilClass
+            'Error tracking and analytic data will now be collected anonymously.'
+          else
+            "Error tracking and analytic data will now be collected as '#{username}'."
+          end
+
+        true
+      end
+    end
+  end
+end
diff --git a/lib/gdk/command/update.rb b/lib/gdk/command/update.rb
index ce675d0de923628138f903f75742d5c9e38a5dc3..1c1f74c995fb3b4e431cf8b10f2f85afed69890d 100644
--- a/lib/gdk/command/update.rb
+++ b/lib/gdk/command/update.rb
@@ -25,15 +25,15 @@ def update!
         GDK::Hooks.with_hooks(config.gdk.update_hooks, 'gdk update') do
           if self_update?
             GDK.make('self-update')
-            GDK.make('self-update', 'update', env: update_env)
+            GDK.make('self-update', 'update', env: update_env).success?
           else
-            GDK.make('update', env: update_env)
+            GDK.make('update', env: update_env).success?
           end
         end
       end
 
       def reconfigure!
-        GDK.make('reconfigure-tasks')
+        GDK.make('reconfigure-tasks').success?
       end
 
       def self_update?
diff --git a/lib/gdk/config.rb b/lib/gdk/config.rb
index ac1764f3bcbb1d29e6748c4784bdb60e99cfa7c8..e37a5b908644f2761a405d7cb72dc28062f48d79 100644
--- a/lib/gdk/config.rb
+++ b/lib/gdk/config.rb
@@ -43,6 +43,11 @@ class Config < ConfigSettings
       string(:ca_path) { '' }
     end
 
+    settings :telemetry do
+      string(:username) { '' }
+      bool(:enabled) { false }
+    end
+
     settings :repositories do
       string(:charts_gitlab) { 'https://gitlab.com/gitlab-org/charts/gitlab.git' }
       string(:gitaly) { 'https://gitlab.com/gitlab-org/gitaly.git' }
diff --git a/lib/gdk/diagnostic/ruby_gems.rb b/lib/gdk/diagnostic/ruby_gems.rb
index 0c96c1ad8dd2b0c6351ef34bc831273369bc6650..5350f7468678ec2c354b22e348138f45ab873edd 100644
--- a/lib/gdk/diagnostic/ruby_gems.rb
+++ b/lib/gdk/diagnostic/ruby_gems.rb
@@ -6,7 +6,7 @@ module GDK
   module Diagnostic
     class RubyGems < Base
       TITLE = 'Ruby Gems'
-      GITLAB_GEMS_TO_CHECK = %w[charlock_holmes ffi gpgme pg oj].freeze
+      GITLAB_GEMS_WITH_C_CODE_TO_CHECK = %w[charlock_holmes ffi gpgme pg oj].freeze
 
       def initialize(allow_gem_not_installed: false)
         @allow_gem_not_installed = allow_gem_not_installed
@@ -31,7 +31,7 @@ def allow_gem_not_installed?
       end
 
       def failed_to_load_gitlab_gems
-        @failed_to_load_gitlab_gems ||= GITLAB_GEMS_TO_CHECK.reject { |name| gem_ok?(name) }
+        @failed_to_load_gitlab_gems ||= GITLAB_GEMS_WITH_C_CODE_TO_CHECK.reject { |name| gem_ok?(name) }
       end
 
       def gem_ok?(name)
diff --git a/lib/gdk/erb_renderer.rb b/lib/gdk/erb_renderer.rb
index a591e78b8daaf7d6eb1c14483df3fac197642f2b..c59e138862aaf1dfde1e586811c5cc04e84ca59e 100644
--- a/lib/gdk/erb_renderer.rb
+++ b/lib/gdk/erb_renderer.rb
@@ -34,7 +34,7 @@ def safe_render!
       FileUtils.mkdir_p(File.dirname(target)) # Ensure target's directory exists
       FileUtils.mv(temp_file.path, target)
     rescue GDK::ConfigSettings::UnsupportedConfiguration => e
-      GDK::Output.abort("#{e.message}.")
+      GDK::Output.abort("#{e.message}.", e)
       false
     ensure
       temp_file&.close
@@ -49,7 +49,7 @@ def render!(target = @target)
 
       File.write(target, result)
     rescue GDK::ConfigSettings::UnsupportedConfiguration => e
-      GDK::Output.abort("#{e.message}.")
+      GDK::Output.abort("#{e.message}.", e)
       false
     end
 
diff --git a/lib/gdk/hooks.rb b/lib/gdk/hooks.rb
index 9dc78430602aecef7fe34b0fc604bcd74f329e6d..68aeb0a57dbe4b776ac6a16ff720d3cbbdb0dc63 100644
--- a/lib/gdk/hooks.rb
+++ b/lib/gdk/hooks.rb
@@ -29,7 +29,7 @@ def self.execute_hook_cmd(cmd, description)
 
       true
     rescue HookCommandError, Shellout::StreamCommandFailedError => e
-      GDK::Output.abort(e.message)
+      GDK::Output.abort(e.message, e)
     end
   end
 end
diff --git a/lib/gdk/output.rb b/lib/gdk/output.rb
index aabba8d469618621dcebf2a359c173485c3e8fae..5297f67e67077e683c748bb7ec4e92695cad16b3 100644
--- a/lib/gdk/output.rb
+++ b/lib/gdk/output.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require_relative '../telemetry'
+
 module GDK
   module Output
     COLOR_CODE_RED = '31'
@@ -100,11 +102,15 @@ def format_error(message)
         icon(:error) + wrap_in_color('ERROR', COLOR_CODE_RED) + ": #{message}"
       end
 
-      def error(message)
+      def error(message, exception = nil)
+        Telemetry.capture_exception(exception || message)
+
         puts(format_error(message), stderr: true)
       end
 
-      def abort(message)
+      def abort(message, exception = nil)
+        Telemetry.capture_exception(exception || message)
+
         Kernel.abort(format_error(message))
       end
 
diff --git a/lib/gdk/postgresql_upgrader.rb b/lib/gdk/postgresql_upgrader.rb
index a70981149c2fe38a41f2494414482acab05377f6..1b21561bef0fea610e8b23097306fadd4b044872 100644
--- a/lib/gdk/postgresql_upgrader.rb
+++ b/lib/gdk/postgresql_upgrader.rb
@@ -41,7 +41,7 @@ def upgrade!
         pg_replica_upgrade('replica_2')
       rescue StandardError => e
         success = false
-        GDK::Output.error "An error occurred: #{e}"
+        GDK::Output.error("An error occurred: #{e}", e)
         GDK::Output.warn 'Rolling back..'
         rename_current_data_dir_back
       end
diff --git a/lib/gdk/project/git_worktree.rb b/lib/gdk/project/git_worktree.rb
index 680d6de7d8923bac7a179fe7d56c5eb4d5b8982d..82075329a89d713758ccfdebb0a8e482e264eef4 100644
--- a/lib/gdk/project/git_worktree.rb
+++ b/lib/gdk/project/git_worktree.rb
@@ -18,7 +18,7 @@ def update
         sh = execute_command(fetch_cmd)
         unless sh.success?
           GDK::Output.puts(sh.read_stderr, stderr: true)
-          GDK::Output.error("Failed to fetch for '#{short_worktree_path}'")
+          GDK::Output.error("Failed to fetch for '#{short_worktree_path}'", sh.read_stderr)
           return false
         end
 
@@ -58,7 +58,7 @@ def checkout_revision
           true
         else
           GDK::Output.puts(sh.read_stderr, stderr: true)
-          GDK::Output.error("Failed to fetch and check out '#{revision}' for '#{short_worktree_path}'")
+          GDK::Output.error("Failed to fetch and check out '#{revision}' for '#{short_worktree_path}'", sh.read_stderr)
           false
         end
       end
@@ -72,7 +72,7 @@ def pull_ff_only
           true
         else
           GDK::Output.puts(sh.read_stderr, stderr: true)
-          GDK::Output.error("Failed to pull (--ff-only) for for '#{short_worktree_path}'")
+          GDK::Output.error("Failed to pull (--ff-only) for for '#{short_worktree_path}'", sh.read_stderr)
           false
         end
       end
@@ -109,7 +109,7 @@ def rebase
           true
         else
           GDK::Output.puts(sh.read_stderr, stderr: true)
-          GDK::Output.error("Failed to rebase '#{default_branch}' on '#{current_branch_name}' for '#{short_worktree_path}'")
+          GDK::Output.error("Failed to rebase '#{default_branch}' on '#{current_branch_name}' for '#{short_worktree_path}'", sh.read_stderr)
           execute_command('git rebase --abort', display_output: false)
           false # Always send false as the initial 'git rebase' failed.
         end
diff --git a/lib/shellout.rb b/lib/shellout.rb
index eb1ce22173049af4b4d20cd2a1c304972825200f..47654e4f3ac4f60ad297b78bf2c530002288bbe5 100644
--- a/lib/shellout.rb
+++ b/lib/shellout.rb
@@ -5,7 +5,7 @@
 
 # Controls execution of commands delegated to the running shell
 class Shellout
-  attr_reader :args, :env, :opts
+  attr_reader :args, :env, :opts, :stderr_str
 
   DEFAULT_EXECUTE_DISPLAY_OUTPUT = true
   DEFAULT_EXECUTE_RETRY_ATTEMPTS = 0
@@ -41,17 +41,17 @@ def execute(display_output: true, display_error: true, retry_attempts: DEFAULT_E
     end
 
     self
-  rescue StreamCommandFailedError, ExecuteCommandFailedError
+  rescue StreamCommandFailedError, ExecuteCommandFailedError => e
     error_message = "'#{command}' failed."
 
     if (retry_attempts -= 1).negative?
-      GDK::Output.error(error_message) if display_error
+      GDK::Output.error(error_message, e) if display_error
 
       self
     else
       retried = true
       error_message += " Retrying in #{retry_delay_secs} secs.."
-      GDK::Output.error(error_message) if display_error
+      GDK::Output.error(error_message, e) if display_error
 
       sleep(retry_delay_secs)
       retry
diff --git a/lib/telemetry.rb b/lib/telemetry.rb
new file mode 100644
index 0000000000000000000000000000000000000000..ee237aee4efe7967059e8ab760db0c15f0fc8afd
--- /dev/null
+++ b/lib/telemetry.rb
@@ -0,0 +1,81 @@
+# frozen_string_literal: true
+
+autoload :FileUtils, 'fileutils'
+autoload :GitlabSDK, 'gitlab-sdk'
+autoload :Logger, 'logger'
+autoload :Sentry, 'sentry-ruby'
+autoload :SnowplowTracker, 'snowplow-tracker'
+
+module Telemetry
+  ANALYTICS_APP_ID = '35SLpKmD0ZB-K34dBAz9Tg'
+  ANALYTICS_BASE_URL = 'https://collector.prod-1.gl-product-analytics.com'
+  SENTRY_DSN = 'https://glet_1a56990d202783685f3708b129fde6c0@observe.gitlab.com:443/errortracking/api/v1/projects/48924931'
+
+  def self.with_telemetry(command)
+    return yield unless telemetry_enabled?
+
+    start = Process.clock_gettime(Process::CLOCK_MONOTONIC)
+    client.identify(GDK.config.telemetry.username)
+    client.track("Start #{command} #{ARGV}", {})
+
+    result = yield
+
+    # This is tightly coupled to GDK commands which return false to indicate failure?
+    message = result ? 'Finish' : 'Failed'
+    duration = Process.clock_gettime(Process::CLOCK_MONOTONIC) - start
+    client.track("#{message} #{command} #{ARGV}", { duration: duration })
+
+    result
+  end
+
+  def self.client
+    return @client if @client
+
+    app_id = ENV.fetch('GITLAB_SDK_APP_ID', ANALYTICS_APP_ID)
+    host = ENV.fetch('GITLAB_SDK_HOST', ANALYTICS_BASE_URL)
+
+    SnowplowTracker::LOGGER.level = Logger::WARN
+    @client = GitlabSDK::Client.new(app_id: app_id, host: host)
+  end
+
+  def self.init_sentry
+    Sentry.init do |config|
+      config.dsn = SENTRY_DSN
+      config.breadcrumbs_logger = [:sentry_logger]
+      config.traces_sample_rate = 1.0
+      config.logger.level = Logger::WARN
+    end
+  end
+
+  def self.capture_exception(message)
+    return unless telemetry_enabled?
+
+    if message.is_a?(Exception)
+      exception = message
+    else
+      exception = StandardError.new(message)
+      exception.set_backtrace(caller)
+    end
+
+    init_sentry
+    Sentry.capture_exception(exception)
+  end
+
+  def self.telemetry_enabled?
+    GDK.config.telemetry.enabled
+  end
+
+  def self.update_settings(username)
+    enabled = true
+
+    if username == '.'
+      username = ''
+      enabled = false
+    end
+
+    FileUtils.touch(GDK::Config::FILE)
+    GDK.config.bury!('telemetry.enabled', enabled)
+    GDK.config.bury!('telemetry.username', username)
+    GDK.config.save_yaml!
+  end
+end
diff --git a/spec/lib/gdk/command/install_spec.rb b/spec/lib/gdk/command/install_spec.rb
index e5b0e64cb7c6e62e651390009bd70e7b1c3edd05..8a1b0dac61fb50f2a125fc034d81b0c16b735c98 100644
--- a/spec/lib/gdk/command/install_spec.rb
+++ b/spec/lib/gdk/command/install_spec.rb
@@ -4,16 +4,20 @@
   let(:args) { [] }
 
   context 'when install fails' do
+    let(:sh) { instance_double(Shellout, success?: false, stderr_str: nil) }
+
     it 'returns an error message' do
-      allow(GDK).to receive(:make).with('install')
+      allow(GDK).to receive(:make).with('install').and_return(sh)
 
       expect { subject.run(args) }.to output(/Failed to install/).to_stderr.and output(/You can try the following that may be of assistance/).to_stdout
     end
   end
 
   context 'when install succeeds' do
+    let(:sh) { instance_double(Shellout, success?: true) }
+
     it 'finishes without problem' do
-      allow(GDK).to receive(:make).with('install').and_return('Some output')
+      allow(GDK).to receive(:make).with('install').and_return(sh)
 
       expect { subject.run(args) }.not_to raise_error
     end
diff --git a/spec/lib/gdk/command/pristine_spec.rb b/spec/lib/gdk/command/pristine_spec.rb
index e3e1e791265fd71fbc0f65eff8ac5b89f8cdd8b0..bae8eeca9d68eb0fcea7880a72ccbd49356874d7 100644
--- a/spec/lib/gdk/command/pristine_spec.rb
+++ b/spec/lib/gdk/command/pristine_spec.rb
@@ -14,7 +14,7 @@
       it 'displays an error and returns false', :hide_stdout do
         expect(Runit).to receive(:stop).with(quiet: true).and_return(false)
 
-        expect(GDK::Output).to receive(:error).with("Failed to run 'gdk pristine' - Had an issue with 'gdk_stop'.")
+        expect(GDK::Output).to receive(:error).with("Failed to run 'gdk pristine' - Had an issue with 'gdk_stop'.", RuntimeError)
 
         expect(subject.run).to be(false)
       end
diff --git a/spec/lib/gdk/command/reconfigure_spec.rb b/spec/lib/gdk/command/reconfigure_spec.rb
index 7a38a24470557e50b9449b9a5154296ef0584365..ccca60199b9eaeb532f151cd26b08ec1787c6364 100644
--- a/spec/lib/gdk/command/reconfigure_spec.rb
+++ b/spec/lib/gdk/command/reconfigure_spec.rb
@@ -18,6 +18,7 @@
   end
 
   def stub_make_reconfigure(success:)
-    expect(GDK).to receive(:make).with('reconfigure').and_return(success)
+    sh = instance_double(Shellout, success?: success, stderr_str: nil)
+    expect(GDK).to receive(:make).with('reconfigure').and_return(sh)
   end
 end
diff --git a/spec/lib/gdk/command/reset_data_spec.rb b/spec/lib/gdk/command/reset_data_spec.rb
index 0e90719f178aa4b3fcd6a94f309d7fe8237da8cf..04c7cecd3d4452ca1e4b75e8ed2f1f562ee5998c 100644
--- a/spec/lib/gdk/command/reset_data_spec.rb
+++ b/spec/lib/gdk/command/reset_data_spec.rb
@@ -57,7 +57,7 @@
           stub_postgres_data_move
           allow(FileUtils).to receive(:mv).with(postgresql_data_directory, backup_postgresql_data_directory).and_raise(Errno::ENOENT)
 
-          expect(GDK::Output).to receive(:error).with("Failed to rename path '#{postgresql_data_directory}' to '#{backup_postgresql_data_directory}/' - No such file or directory")
+          expect(GDK::Output).to receive(:error).with("Failed to rename path '#{postgresql_data_directory}' to '#{backup_postgresql_data_directory}/' - No such file or directory", Errno::ENOENT)
           expect(GDK::Output).to receive(:error).with('Failed to backup data.')
           expect(subject).to receive(:display_help_message)
           expect(GDK).not_to receive(:make)
@@ -80,9 +80,10 @@
           travel_to(now) do
             stub_data_moves
 
-            expect(GDK).to receive(:make).with('ensure-databases-setup', 'reconfigure').and_return(false)
+            sh = instance_double(Shellout, success?: false, stderr_str: 'Error')
+            expect(GDK).to receive(:make).with('ensure-databases-setup', 'reconfigure').and_return(sh)
 
-            expect(GDK::Output).to receive(:error).with('Failed to reset data.')
+            expect(GDK::Output).to receive(:error).with('Failed to reset data.', 'Error')
             expect(GDK::Command::Start).not_to receive(:new)
             expect(subject).to receive(:display_help_message)
 
@@ -96,7 +97,8 @@
           travel_to(now) do
             stub_data_moves
 
-            expect(GDK).to receive(:make).with('ensure-databases-setup', 'reconfigure').and_return(true)
+            sh = instance_double(Shellout, success?: true)
+            expect(GDK).to receive(:make).with('ensure-databases-setup', 'reconfigure').and_return(sh)
 
             expect(GDK::Output).to receive(:notice).with("Moving PostgreSQL data from '#{postgresql_data_directory}' to '#{backup_postgresql_data_directory}/'")
             expect(GDK::Output).to receive(:notice).with("Moving redis dump.rdb from '#{redis_dump_rdb_path}' to '#{backup_redis_dump_rdb_path}/'")
diff --git a/spec/lib/gdk/command/update_spec.rb b/spec/lib/gdk/command/update_spec.rb
index e096fdbe2795c07352baa73a4370a69f9bd89cbf..3d33b4e47b0cddb2d1e1e83e6433f1520908a2cf 100644
--- a/spec/lib/gdk/command/update_spec.rb
+++ b/spec/lib/gdk/command/update_spec.rb
@@ -1,9 +1,11 @@
 # frozen_string_literal: true
 
 RSpec.describe GDK::Command::Update do
+  let(:sh) { instance_double(Shellout, success?: true) }
+
   before do
     allow(GDK::Hooks).to receive(:execute_hooks)
-    allow(GDK).to receive(:make)
+    allow(GDK).to receive(:make).and_return(sh)
   end
 
   describe '#run' do
diff --git a/spec/lib/gdk/diagnostic/ruby_gems_spec.rb b/spec/lib/gdk/diagnostic/ruby_gems_spec.rb
index 31fc9607e692e7b6f2e15d4d4fe24270d5c6dd13..e3a17b32c859c005c115d8e425dcd041f69e021f 100644
--- a/spec/lib/gdk/diagnostic/ruby_gems_spec.rb
+++ b/spec/lib/gdk/diagnostic/ruby_gems_spec.rb
@@ -6,7 +6,7 @@
   subject(:diagnostic) { described_class.new(allow_gem_not_installed: allow_gem_not_installed) }
 
   before do
-    stub_const('GDK::Diagnostic::RubyGems::GITLAB_GEMS_TO_CHECK', %w[bad_gem])
+    stub_const('GDK::Diagnostic::RubyGems::GITLAB_GEMS_WITH_C_CODE_TO_CHECK', %w[bad_gem])
   end
 
   describe '#success?' do
diff --git a/spec/lib/gdk/project/git_worktree_spec.rb b/spec/lib/gdk/project/git_worktree_spec.rb
index 693742287098eea3d74931e8d30135420f51c489..5c0f4b32f09cd7cb50fc5b4f27e1e2aff446a760 100644
--- a/spec/lib/gdk/project/git_worktree_spec.rb
+++ b/spec/lib/gdk/project/git_worktree_spec.rb
@@ -32,7 +32,7 @@
       it 'fetch fails, but stash pops' do
         expect_update(stash_result: stash_saved_something, fetch_success: false, shallow_clone: shallow_clone)
         expect(GDK::Output).to receive(:puts).with("fetch_success: false", stderr: true)
-        expect(GDK::Output).to receive(:error).with("Failed to fetch for '#{short_worktree_path}'")
+        expect(GDK::Output).to receive(:error).with("Failed to fetch for '#{short_worktree_path}'", 'fetch_success: false')
         expect_shellout('git stash pop')
         expect(subject.update).to be_falsey
       end
@@ -71,7 +71,7 @@
       it 'fetch fails, but stash pops' do
         expect_update(stash_result: stash_saved_something, fetch_success: false, shallow_clone: shallow_clone)
         expect(GDK::Output).to receive(:puts).with("fetch_success: false", stderr: true)
-        expect(GDK::Output).to receive(:error).with("Failed to fetch for '#{short_worktree_path}'")
+        expect(GDK::Output).to receive(:error).with("Failed to fetch for '#{short_worktree_path}'", "fetch_success: false")
         expect_shellout('git stash pop')
         expect(subject.update).to be_falsey
       end
@@ -144,7 +144,7 @@ def expect_auto_rebase(rebase_success = true)
         expect(GDK::Output).to receive(:success).with("Successfully fetched and rebased '#{default_branch}' on '#{current_branch_name}' for '#{short_worktree_path}'")
       else
         expect(GDK::Output).to receive(:puts).with(stderr, stderr: true)
-        expect(GDK::Output).to receive(:error).with("Failed to rebase '#{default_branch}' on '#{current_branch_name}' for '#{short_worktree_path}'")
+        expect(GDK::Output).to receive(:error).with("Failed to rebase '#{default_branch}' on '#{current_branch_name}' for '#{short_worktree_path}'", stderr)
       end
     end
 
@@ -163,12 +163,12 @@ def expect_checkout_and_pull(checkout_success: true, pull_success: true)
             expect(GDK::Output).to receive(:success).with("Successfully pulled (--ff-only) for '#{short_worktree_path}'")
           else
             expect(GDK::Output).to receive(:puts).with(pull_stderr, stderr: true)
-            expect(GDK::Output).to receive(:error).with("Failed to pull (--ff-only) for for '#{short_worktree_path}'")
+            expect(GDK::Output).to receive(:error).with("Failed to pull (--ff-only) for for '#{short_worktree_path}'", pull_stderr)
           end
         end
       else
         expect(GDK::Output).to receive(:puts).with(checkout_stderr, stderr: true)
-        expect(GDK::Output).to receive(:error).with("Failed to fetch and check out '#{revision}' for '#{short_worktree_path}'")
+        expect(GDK::Output).to receive(:error).with("Failed to fetch and check out '#{revision}' for '#{short_worktree_path}'", checkout_stderr)
       end
     end
 
@@ -181,7 +181,7 @@ def expect_just_checkout(checkout_success = true)
         expect(GDK::Output).to receive(:success).with("Successfully fetched and checked out '#{revision}' for '#{short_worktree_path}'")
       else
         expect(GDK::Output).to receive(:puts).with(checkout_stderr, stderr: true)
-        expect(GDK::Output).to receive(:error).with("Failed to fetch and check out '#{revision}' for '#{short_worktree_path}'")
+        expect(GDK::Output).to receive(:error).with("Failed to fetch and check out '#{revision}' for '#{short_worktree_path}'", checkout_stderr)
       end
     end
 
diff --git a/spec/lib/gdk/telemetry_spec.rb b/spec/lib/gdk/telemetry_spec.rb
new file mode 100644
index 0000000000000000000000000000000000000000..c618bce0dffe8fbb8c7dec25b692e92268667691
--- /dev/null
+++ b/spec/lib/gdk/telemetry_spec.rb
@@ -0,0 +1,184 @@
+# frozen_string_literal: true
+
+require 'fileutils'
+require 'gitlab-sdk'
+require 'sentry-ruby'
+require 'snowplow-tracker'
+
+# rubocop:disable RSpec/ExpectInHook
+RSpec.describe Telemetry do
+  describe '.with_telemetry' do
+    let(:command) { 'test_command' }
+    let(:args) { %w[arg1 arg2] }
+    let(:telemetry_enabled) { true }
+
+    before do
+      expect(described_class).to receive(:telemetry_enabled?).and_return(telemetry_enabled)
+      expect(described_class).to receive(:with_telemetry).and_call_original
+
+      allow(GDK).to receive_message_chain(:config, :telemetry, :username).and_return('testuser')
+      allow(described_class).to receive(:client)
+
+      stub_const('ARGV', args)
+    end
+
+    context 'when telemetry is not enabled' do
+      let(:telemetry_enabled) { false }
+
+      it 'does not track telemetry and directly yields the block' do
+        expect { |b| described_class.with_telemetry(command, &b) }.to yield_control
+      end
+    end
+
+    it 'tracks the start and finish of the command' do
+      expect(described_class).to receive_message_chain(:client, :identify).with('testuser')
+      expect(described_class).to receive_message_chain(:client, :track).with("Start #{command} #{args.inspect}", {})
+      expect(described_class).to receive_message_chain(:client, :track).with(a_string_starting_with('Finish'), hash_including(:duration))
+
+      described_class.with_telemetry(command) { true }
+    end
+
+    context 'when the block returns false' do
+      it 'tracks the start and failure of the command' do
+        expect(described_class).to receive_message_chain(:client, :identify).with('testuser')
+        expect(described_class).to receive_message_chain(:client, :track).with("Start #{command} #{args.inspect}", {})
+        expect(described_class).to receive_message_chain(:client, :track).with(a_string_starting_with('Failed'), hash_including(:duration))
+
+        described_class.with_telemetry(command) { false }
+      end
+    end
+  end
+
+  describe '.client' do
+    before do
+      described_class.instance_variable_set(:@client, nil)
+
+      stub_env('GITLAB_SDK_APP_ID', 'app_id')
+      stub_env('GITLAB_SDK_HOST', 'https://collector')
+
+      allow(GitlabSDK::Client).to receive(:new).and_return(mocked_client)
+    end
+
+    let(:mocked_client) { instance_double(GitlabSDK::Client) }
+
+    it 'initializes the gitlab sdk client with the correct configuration' do
+      expect(SnowplowTracker::LOGGER).to receive(:level=).with(Logger::WARN)
+      expect(GitlabSDK::Client).to receive(:new).with(app_id: 'app_id', host: 'https://collector').and_return(mocked_client)
+
+      described_class.client
+    end
+
+    context 'when client is already initialized' do
+      before do
+        described_class.instance_variable_set(:@client, mocked_client)
+      end
+
+      it 'returns the existing client without reinitializing' do
+        expect(GitlabSDK::Client).not_to receive(:new)
+        expect(described_class.client).to eq(mocked_client)
+      end
+    end
+  end
+
+  describe '.init_sentry' do
+    let(:config) { instance_double(Sentry::Configuration) }
+
+    it 'initializes the sentry client with expected values' do
+      allow(Sentry).to receive(:init).and_yield(config)
+
+      expect(config).to receive(:dsn=).with('https://glet_1a56990d202783685f3708b129fde6c0@observe.gitlab.com:443/errortracking/api/v1/projects/48924931')
+      expect(config).to receive(:breadcrumbs_logger=).with([:sentry_logger])
+      expect(config).to receive(:traces_sample_rate=).with(1.0)
+      expect(config).to receive_message_chain(:logger, :level=).with(Logger::WARN)
+
+      described_class.init_sentry
+    end
+  end
+
+  describe '.telemetry_enabled?' do
+    [true, false].each do |value|
+      context "when #{value}" do
+        it "returns #{value}" do
+          expect(GDK).to receive_message_chain(:config, :telemetry, :enabled).and_return(value)
+
+          expect(described_class.telemetry_enabled?).to eq(value)
+        end
+      end
+    end
+  end
+
+  describe '.update_settings' do
+    before do
+      expect(FileUtils).to receive(:touch)
+      expect(GDK.config).to receive(:save_yaml!)
+    end
+
+    context 'when username is not .' do
+      let(:username) { 'testuser' }
+
+      it 'updates the settings with the provided username and enables telemetry' do
+        expect(GDK.config).to receive(:bury!).with('telemetry.enabled', true)
+        expect(GDK.config).to receive(:bury!).with('telemetry.username', username)
+
+        described_class.update_settings(username)
+      end
+    end
+
+    context 'when username is .' do
+      let(:username) { '.' }
+
+      it 'updates the settings with an empty username and disables telemetry' do
+        expect(GDK.config).to receive(:bury!).with('telemetry.enabled', false)
+        expect(GDK.config).to receive(:bury!).with('telemetry.username', '')
+
+        described_class.update_settings(username)
+      end
+    end
+  end
+
+  describe '.capture_exception' do
+    let(:telemetry_enabled) { true }
+
+    before do
+      expect(described_class).to receive(:telemetry_enabled?).and_return(telemetry_enabled)
+
+      allow(described_class).to receive(:capture_exception).and_call_original
+      allow(described_class).to receive(:init_sentry)
+    end
+
+    context 'when telemetry is not enabled' do
+      let(:telemetry_enabled) { false }
+
+      it 'does not capture the exception' do
+        expect(Sentry).not_to receive(:capture_exception)
+
+        described_class.capture_exception('Test error')
+      end
+    end
+
+    context 'when given an exception' do
+      let(:exception) { StandardError.new('Test error') }
+
+      it 'captures the given exception' do
+        expect(Sentry).to receive(:capture_exception).with(exception)
+
+        described_class.capture_exception(exception)
+      end
+    end
+
+    context 'when given a string' do
+      let(:message) { 'Test error message' }
+
+      it 'captures a new exception with the given message' do
+        expect(Sentry).to receive(:capture_exception) do |exception|
+          expect(exception).to be_a(StandardError)
+          expect(exception.message).to eq(message)
+          expect(exception.backtrace).not_to be_empty
+        end
+
+        described_class.capture_exception(message)
+      end
+    end
+  end
+end
+# rubocop:enable RSpec/ExpectInHook
diff --git a/spec/lib/gdk_spec.rb b/spec/lib/gdk_spec.rb
index b5ebdbfd01bf4314c1597e635e193f49272fd47a..448302020cf36c65dd755b1ccff29b3bc3bba584 100644
--- a/spec/lib/gdk_spec.rb
+++ b/spec/lib/gdk_spec.rb
@@ -68,7 +68,7 @@ def expect_output(level, message: nil)
 
     shared_examples 'invalid YAML' do |error_message|
       it 'prints an error' do
-        expect(GDK::Output).to receive(:error).with("Your gdk.yml is invalid.\n\n")
+        expect(GDK::Output).to receive(:error).with("Your gdk.yml is invalid.\n\n", StandardError)
         expect(GDK::Output).to receive(:puts).with(error_message, stderr: true)
 
         expect { described_class.validate_yaml! }.to raise_error(SystemExit).and output("\n").to_stderr
diff --git a/spec/lib/shellout_spec.rb b/spec/lib/shellout_spec.rb
index 505f272203d8160da6f530278aab9e55557c060c..0a9183818531ff70238100b86238375f87a88973 100644
--- a/spec/lib/shellout_spec.rb
+++ b/spec/lib/shellout_spec.rb
@@ -112,7 +112,7 @@
 
         it 'displays output and errors' do
           expect(GDK::Output).to receive(:print).with(expected_command_stderr_puts, stderr: true)
-          expect(GDK::Output).to receive(:error).with(expected_command_error)
+          expect(GDK::Output).to receive(:error).with(expected_command_error, Shellout::ShelloutBaseError)
 
           subject.execute
         end
@@ -132,8 +132,8 @@
           expect(subject).to receive(expected_execute_method).exactly(3).times # 1 for the first run + 2 retries
           expect(subject).to receive(:success?).exactly(6).times.and_return(false)
 
-          expect(GDK::Output).to receive(:error).with("'#{command}' failed. Retrying in 2 secs..").twice
-          expect(GDK::Output).to receive(:error).with("'#{command}' failed.")
+          expect(GDK::Output).to receive(:error).with("'#{command}' failed. Retrying in 2 secs..", Shellout::ExecuteCommandFailedError).twice
+          expect(GDK::Output).to receive(:error).with("'#{command}' failed.", Shellout::ExecuteCommandFailedError)
 
           subject.execute(display_output: display_output, retry_attempts: 2)
         end
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 956bd5954ae6a307e58774dd8bcf701ceebb183d..442b4aaf3807fc6d5928044acd359720d52584e2 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -14,6 +14,7 @@
 
 require_relative '../lib/gdk'
 require_relative '../lib/gdk/task_helpers'
+require_relative '../lib/telemetry'
 
 RSpec.configure do |config|
   config.before do |example|
@@ -45,6 +46,13 @@
 
       allow(GDK).to receive(:root).and_return(gdk_root_tmp_path)
     end
+
+    unless example.metadata[:with_telemetry]
+      allow(Telemetry).to receive(:with_telemetry).and_wrap_original do |_method, *_args, &block|
+        block.call
+      end
+      allow(Telemetry).to receive(:capture_exception)
+    end
   end
 
   config.disable_monkey_patching
diff --git a/support/install b/support/install
index 6ae1c8705008a4be3b58cd9d54c034d41ba826a8..a98bb6e04d3f9284ed0fe897ec67aa3084f4e162 100755
--- a/support/install
+++ b/support/install
@@ -66,7 +66,7 @@ bootstrap() {
 gdk_install() {
   # shellcheck disable=SC1090
   source "${ASDF_SH_PATH}"
-  gdk install gitlab_repo="$GITLAB_REPO_URL"
+  gdk install gitlab_repo="$GITLAB_REPO_URL" telemetry_user="$GITLAB_USERNAME"
 }
 
 echo
@@ -80,13 +80,20 @@ echo
 if [ $# -eq 1 ]; then
   echo "Where would you like to install the GDK? [./${DEFAULT_GDK_INSTALL_DIR}]"
   read -r GDK_INSTALL_DIR </dev/tty
-
+  echo
   echo "Which GitLab repo URL would you like to clone? [${DEFAULT_GITLAB_REPO_URL}]"
   echo
   echo "ATTENTION: For members of the wider community, it is recommended to use the community fork (https://gitlab.com/gitlab-community/gitlab.git)."
   echo "See https://gitlab.com/gitlab-community/meta for instructions on how to join."
   echo "If you'd prefer to use your own repository, please ensure that its visibility is set to public."
   read -r GITLAB_REPO_URL </dev/tty
+  echo
+  echo "To improve GDK, GitLab would like to collect basic error and usage data. Please choose one of the following options:"
+  echo
+  echo "- To send data to GitLab, enter your GitLab username."
+  echo "- To send data to GitLab anonymously, leave blank."
+  echo "- To avoid sending data to GitLab, enter a period ('.')."
+  read -r GITLAB_USERNAME </dev/tty
 else
   GDK_INSTALL_DIR="${2-gitlab-development-kit}"
   GDK_CLONE_BRANCH="${3-main}"
diff --git a/support/test_url b/support/test_url
index eed23cbc81b75c3d42c1aac491615708862f60e0..fb2d315c3f154503bf111b09c0fe541c3842a7b8 100755
--- a/support/test_url
+++ b/support/test_url
@@ -9,7 +9,7 @@ verbose = ENV['QUIET'] == 'false'
 
 begin
   exit(GDK::TestURL.new(url).wait(verbose: verbose))
-rescue GDK::TestURL::UrlAppearsInvalid
-  GDK::Output.error("'#{url}' does not appear to be a valid URL?")
+rescue GDK::TestURL::UrlAppearsInvalid => e
+  GDK::Output.error("'#{url}' does not appear to be a valid URL?", e)
   exit(1)
 end