diff --git a/bin/changelog b/bin/changelog
index d7b2a1a2de9b524601c3fd2079383c238dd7f31d..758c036161e6d5d978f850fb7cc371a1973a81f4 100755
--- a/bin/changelog
+++ b/bin/changelog
@@ -23,6 +23,8 @@ module ChangelogHelpers
   Abort = Class.new(StandardError)
   Done = Class.new(StandardError)
 
+  MAX_FILENAME_LENGTH = 140 # ecryptfs has a limit of 140 characters
+
   def capture_stdout(cmd)
     output = IO.popen(cmd, &:read)
     fail_with "command failed: #{cmd.join(' ')}" unless $?.success?
@@ -142,7 +144,9 @@ class ChangelogEntry
 
   def initialize(options)
     @options = options
+  end
 
+  def execute
     assert_feature_branch!
     assert_title!
     assert_new_file!
@@ -221,10 +225,12 @@ class ChangelogEntry
   end
 
   def file_path
-    File.join(
+    base_path = File.join(
       unreleased_path,
-      branch_name.gsub(/[^\w-]/, '-') << '.yml'
-    )
+      branch_name.gsub(/[^\w-]/, '-'))
+
+    # Add padding for .yml extension
+    base_path[0..MAX_FILENAME_LENGTH - 5] + '.yml'
   end
 
   def unreleased_path
@@ -250,7 +256,7 @@ end
 if $0 == __FILE__
   begin
     options = ChangelogOptionParser.parse(ARGV)
-    ChangelogEntry.new(options)
+    ChangelogEntry.new(options).execute
   rescue ChangelogHelpers::Abort => ex
     $stderr.puts ex.message
     exit 1
diff --git a/spec/bin/changelog_spec.rb b/spec/bin/changelog_spec.rb
index f278043028f09295081c606d184e62367c46de8b..9dc4edf97d1f7d34c3feb12b96754a923b13f424 100644
--- a/spec/bin/changelog_spec.rb
+++ b/spec/bin/changelog_spec.rb
@@ -3,6 +3,20 @@ require 'spec_helper'
 load File.expand_path('../../bin/changelog', __dir__)
 
 describe 'bin/changelog' do
+  let(:options) { OpenStruct.new(title: 'Test title', type: 'fixed', dry_run: true) }
+
+  describe ChangelogEntry do
+    it 'truncates the file path' do
+      entry = described_class.new(options)
+
+      allow(entry).to receive(:ee?).and_return(false)
+      allow(entry).to receive(:branch_name).and_return('long-branch-' * 100)
+
+      file_path = entry.send(:file_path)
+      expect(file_path.length).to eq(140)
+    end
+  end
+
   describe ChangelogOptionParser do
     describe '.parse' do
       it 'parses --amend' do