diff --git a/CHANGELOG.md b/CHANGELOG.md
index fe3d6561c..a7036f100 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,7 +10,7 @@ _None_
 
 ### New Features
 
-_None_
+- Improve failure message when pinned commit cannot be found during `configure_update` [#410]
 
 ### Bug Fixes
 
diff --git a/lib/fastlane/plugin/wpmreleasetoolkit/helper/configure_helper.rb b/lib/fastlane/plugin/wpmreleasetoolkit/helper/configure_helper.rb
index 1d58bf4c1..5cce113df 100644
--- a/lib/fastlane/plugin/wpmreleasetoolkit/helper/configure_helper.rb
+++ b/lib/fastlane/plugin/wpmreleasetoolkit/helper/configure_helper.rb
@@ -3,6 +3,7 @@
 require 'English'
 require 'fastlane_core/ui/ui'
 require 'fileutils'
+require 'git'
 
 require_relative '../models/configuration'
 
@@ -74,8 +75,10 @@ def self.update_configure_file_commit_hash(new_hash)
       ### Returns the currently checked out branch for the `~/.mobile-secrets` repository.
       ### NB: Returns nil if the repo is in a detached HEAD state.
       def self.repo_branch_name
-        result = `cd #{repository_path} && git rev-parse --abbrev-ref HEAD`.strip
-        result == 'HEAD' ? nil : result
+        git = Git.open(repository_path)
+        return nil if git.branches.select(&:current).empty?
+
+        git.current_branch
       end
 
       ### Returns the most recent commit hash in the `~/.mobile-secrets` repository.
@@ -102,11 +105,16 @@ def self.configure_file_is_behind_local
       end
 
       def self.configure_file_commits_behind_repo
-        # Get a sily number of revisions to ensure we don't miss any
+        # Get a large number of revisions to ensure we don't miss any
         result = `cd #{repository_path} && git --no-pager log -10000 --pretty=format:"%H" && echo`
         hashes = result.each_line.map(&:strip).reverse
 
         index_of_configure_hash = hashes.find_index(configure_file_commit_hash)
+
+        UI.user_error!("Could not find Git commit #{configure_file_commit_hash} from `.configure` file in local secrets repository. Please verify your local copy is up to date with the remote.") if index_of_configure_hash.nil?
+
+        # No need to check for this to be `nil` because it comes by reading the
+        # local `.mobile-secrets` repo itself.
         index_of_repo_commit_hash = hashes.find_index(repo_commit_hash)
 
         return 0 if index_of_configure_hash >= index_of_repo_commit_hash
diff --git a/spec/configure_helper_spec.rb b/spec/configure_helper_spec.rb
index 221e1a64a..d0e4a0318 100644
--- a/spec/configure_helper_spec.rb
+++ b/spec/configure_helper_spec.rb
@@ -1,8 +1,48 @@
 # frozen_string_literal: true
 
 require 'spec_helper'
+require 'tmpdir'
 
 describe Fastlane::Helper::ConfigureHelper do
+  let(:test_repo_path) { Dir.mktmpdir }
+
+  def run_git_command(command:, repo_path: test_repo_path)
+    # Notice that this will break if the command contains arguments in quotes,
+    # e.g. `commit -m "Test commit"` will be split into `['commit', '-m', '"Test', 'commit"']`
+    # which is not a valid arguments list for Git.
+    #
+    # For the context of these tests, we can deal with this limitation.
+    system('git', '-C', repo_path, *command.split, %I[out err] => File::NULL)
+  end
+
+  before do
+    allow(described_class).to receive(:repository_path).and_return(test_repo_path)
+
+    run_git_command(command: 'init')
+    run_git_command(command: 'config user.email test@example.com')
+    run_git_command(command: 'config user.name Test User')
+    File.write(File.join(test_repo_path, 'test.txt'), 'test content')
+    run_git_command(command: 'add test.txt')
+    run_git_command(command: 'commit -m test')
+  end
+
+  after do
+    FileUtils.remove_entry test_repo_path
+  end
+
+  describe '.repo_branch_name' do
+    it 'returns the current branch name when on a branch' do
+      run_git_command(command: 'checkout -b feature-branch')
+      expect(described_class.repo_branch_name).to eq('feature-branch')
+    end
+
+    it 'returns nil when in detached HEAD state' do
+      current_sha = `git -C #{test_repo_path} rev-parse HEAD`.strip
+      run_git_command(command: "checkout #{current_sha}")
+      expect(described_class.repo_branch_name).to be_nil
+    end
+  end
+
   describe '#add_file' do
     let(:destination) { 'path/to/destination' }