diff --git a/app/models/repository.rb b/app/models/repository.rb
index c646f567b949644f1b3badc584934e940ad65511..ef204170732c90b9768dc0616d19d6979732e2a4 100644
--- a/app/models/repository.rb
+++ b/app/models/repository.rb
@@ -1059,6 +1059,10 @@ def lfsconfig_for(sha)
     blob_data_at(sha, '.lfsconfig')
   end
 
+  def changelog_config(ref = 'HEAD')
+    blob_data_at(ref, Gitlab::Changelog::Config::FILE_PATH)
+  end
+
   def fetch_ref(source_repository, source_ref:, target_ref:)
     raw_repository.fetch_ref(source_repository.raw_repository, source_ref: source_ref, target_ref: target_ref)
   end
diff --git a/lib/gitlab/changelog/committer.rb b/lib/gitlab/changelog/committer.rb
new file mode 100644
index 0000000000000000000000000000000000000000..d2563590bed7b4984306594a3b5e5ef9e603552e
--- /dev/null
+++ b/lib/gitlab/changelog/committer.rb
@@ -0,0 +1,65 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    # A class used for committing a release's changelog to a Git repository.
+    class Committer
+      CommitError = Class.new(StandardError)
+
+      def initialize(project, user)
+        @project = project
+        @user = user
+      end
+
+      # Commits a release's changelog to a file on a branch.
+      #
+      # The `release` argument is a `Gitlab::Changelog::Release` for which to
+      # update the changelog.
+      #
+      # The `file` argument specifies the path to commit the changes to.
+      #
+      # The `branch` argument specifies the branch to commit the changes on.
+      #
+      # The `message` argument specifies the commit message to use.
+      def commit(release:, file:, branch:, message:)
+        # When retrying, we need to reprocess the existing changelog from
+        # scratch, otherwise we may end up throwing away changes. As such, all
+        # the logic is contained within the retry block.
+        Retriable.retriable(on: CommitError) do
+          commit = @project.commit(branch)
+          content = blob_content(file, commit)
+
+          # If the release has already been added (e.g. concurrently by another
+          # API call), we don't want to add it again.
+          break if content&.match?(release.header_start_pattern)
+
+          service = Files::MultiService.new(
+            @project,
+            @user,
+            commit_message: message,
+            branch_name: branch,
+            start_branch: branch,
+            actions: [
+              {
+                action: content ? 'update' : 'create',
+                content: Generator.new(content.to_s).add(release),
+                file_path: file,
+                last_commit_id: commit&.sha
+              }
+            ]
+          )
+
+          result = service.execute
+
+          raise CommitError.new(result[:message]) if result[:status] != :success
+        end
+      end
+
+      def blob_content(file, commit = nil)
+        return unless commit
+
+        @project.repository.blob_at(commit.sha, file)&.data
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/changelog/config.rb b/lib/gitlab/changelog/config.rb
new file mode 100644
index 0000000000000000000000000000000000000000..ac62572576e2bacfa62ccafd67e26a27c0545cc7
--- /dev/null
+++ b/lib/gitlab/changelog/config.rb
@@ -0,0 +1,74 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    # Configuration settings used when generating changelogs.
+    class Config
+      ConfigError = Class.new(StandardError)
+
+      # When rendering changelog entries, authors are not included.
+      AUTHORS_NONE = 'none'
+
+      # The path to the configuration file as stored in the project's Git
+      # repository.
+      FILE_PATH = '.gitlab/changelog_config.yml'
+
+      # The default date format to use for formatting release dates.
+      DEFAULT_DATE_FORMAT = '%Y-%m-%d'
+
+      # The default template to use for generating release sections.
+      DEFAULT_TEMPLATE = File.read(File.join(__dir__, 'template.tpl'))
+
+      attr_accessor :date_format, :categories, :template
+
+      def self.from_git(project)
+        if (yaml = project.repository.changelog_config)
+          from_hash(project, YAML.safe_load(yaml))
+        else
+          new(project)
+        end
+      end
+
+      def self.from_hash(project, hash)
+        config = new(project)
+
+        if (date = hash['date_format'])
+          config.date_format = date
+        end
+
+        if (template = hash['template'])
+          config.template = Template::Compiler.new.compile(template)
+        end
+
+        if (categories = hash['categories'])
+          if categories.is_a?(Hash)
+            config.categories = categories
+          else
+            raise ConfigError, 'The "categories" configuration key must be a Hash'
+          end
+        end
+
+        config
+      end
+
+      def initialize(project)
+        @project = project
+        @date_format = DEFAULT_DATE_FORMAT
+        @template = Template::Compiler.new.compile(DEFAULT_TEMPLATE)
+        @categories = {}
+      end
+
+      def contributor?(user)
+        @project.team.contributor?(user)
+      end
+
+      def category(name)
+        @categories[name] || name
+      end
+
+      def format_date(date)
+        date.strftime(@date_format)
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/changelog/generator.rb b/lib/gitlab/changelog/generator.rb
new file mode 100644
index 0000000000000000000000000000000000000000..a80ca0728f98595b48949653f4d2b570b9a0960f
--- /dev/null
+++ b/lib/gitlab/changelog/generator.rb
@@ -0,0 +1,59 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    # Parsing and generating of Markdown changelogs.
+    class Generator
+      # The regex used to parse a release header.
+      RELEASE_REGEX =
+        /^##\s+(?<version>#{Gitlab::Regex.unbounded_semver_regex})/.freeze
+
+      # The `input` argument must be a `String` containing the existing
+      # changelog Markdown. If no changelog exists, this should be an empty
+      # `String`.
+      def initialize(input = '')
+        @lines = input.lines
+        @locations = {}
+
+        @lines.each_with_index do |line, index|
+          matches = line.match(RELEASE_REGEX)
+
+          next if !matches || !matches[:version]
+
+          @locations[matches[:version]] = index
+        end
+      end
+
+      # Generates the Markdown for the given release and returns the new
+      # changelog Markdown content.
+      #
+      # The `release` argument must be an instance of
+      # `Gitlab::Changelog::Release`.
+      def add(release)
+        versions = [release.version, *@locations.keys]
+
+        VersionSorter.rsort!(versions)
+
+        new_index = versions.index(release.version)
+        new_lines = @lines.dup
+        markdown = release.to_markdown
+
+        if (insert_after = versions[new_index + 1])
+          line_index = @locations[insert_after]
+
+          new_lines.insert(line_index, markdown)
+        else
+          # When adding to the end of the changelog, the previous section only
+          # has a single newline, resulting in the release section title
+          # following it immediately. When this is the case, we insert an extra
+          # empty line to keep the changelog readable in its raw form.
+          new_lines.push("\n") if versions.length > 1
+          new_lines.push(markdown.rstrip)
+          new_lines.push("\n")
+        end
+
+        new_lines.join
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/changelog/release.rb b/lib/gitlab/changelog/release.rb
new file mode 100644
index 0000000000000000000000000000000000000000..4c78eb5080c7ce673945cf281ede3caa6625946a
--- /dev/null
+++ b/lib/gitlab/changelog/release.rb
@@ -0,0 +1,94 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    # A release to add to a changelog.
+    class Release
+      attr_reader :version
+
+      def initialize(version:, date:, config:)
+        @version = version
+        @date = date
+        @config = config
+        @entries = Hash.new { |h, k| h[k] = [] }
+
+        # This ensures that entries are presented in the same order as the
+        # categories Hash in the user's configuration.
+        @config.categories.values.each do |category|
+          @entries[category] = []
+        end
+      end
+
+      def add_entry(
+        title:,
+        commit:,
+        category:,
+        author: nil,
+        merge_request: nil
+      )
+        # When changing these fields, keep in mind that this needs to be
+        # backwards compatible. For example, you can't just remove a field as
+        # this will break the changelog generation process for existing users.
+        entry = {
+          'title' => title,
+          'commit' => {
+            'reference' => commit.to_reference(full: true),
+            'trailers' => commit.trailers
+          }
+        }
+
+        if author
+          entry['author'] = {
+            'reference' => author.to_reference(full: true),
+            'contributor' => @config.contributor?(author)
+          }
+        end
+
+        if merge_request
+          entry['merge_request'] = {
+            'reference' => merge_request.to_reference(full: true)
+          }
+        end
+
+        @entries[@config.category(category)] << entry
+      end
+
+      def to_markdown
+        # While not critical, we would like release sections to be separated by
+        # an empty line in the changelog; ensuring it's readable even in its
+        # raw form.
+        #
+        # Since it can be a bit tricky to get this right using Liquid, we
+        # enforce an empty line separator ourselves.
+        markdown =
+          @config.template.render('categories' => entries_for_template).strip
+
+        # The release header can't be changed using the Liquid template, as we
+        # need this to be in a known format. Without this restriction, we won't
+        # know where to insert a new release section in an existing changelog.
+        "## #{@version} (#{release_date})\n\n#{markdown}\n\n"
+      end
+
+      def header_start_pattern
+        /^##\s*#{Regexp.escape(@version)}/
+      end
+
+      private
+
+      def release_date
+        @config.format_date(@date)
+      end
+
+      def entries_for_template
+        @entries.map do |category, entries|
+          {
+            'title' => category,
+            'count' => entries.length,
+            'single_change' => entries.length == 1,
+            'entries' => entries
+          }
+        end
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/changelog/template.tpl b/lib/gitlab/changelog/template.tpl
new file mode 100644
index 0000000000000000000000000000000000000000..838b7080f6841140c8dea81b2ebb031f29267682
--- /dev/null
+++ b/lib/gitlab/changelog/template.tpl
@@ -0,0 +1,14 @@
+{% if categories %}
+{% each categories %}
+### {{ title }} ({% if single_change %}1 change{% else %}{{ count }} changes{% end %})
+
+{% each entries %}
+- [{{ title }}]({{ commit.reference }})\
+{% if author.contributor %} by {{ author.reference }}{% end %}\
+{% if merge_request %} ([merge request]({{ merge_request.reference }})){% end %}
+{% end %}
+
+{% end %}
+{% else %}
+No changes.
+{% end %}
diff --git a/lib/gitlab/changelog/template/compiler.rb b/lib/gitlab/changelog/template/compiler.rb
new file mode 100644
index 0000000000000000000000000000000000000000..f67bab0f29fa0b31fb17f0ac095d3959c15ff501
--- /dev/null
+++ b/lib/gitlab/changelog/template/compiler.rb
@@ -0,0 +1,146 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    module Template
+      # Compiler is used for turning a minimal user templating language into an
+      # ERB template, without giving the user access to run arbitrary code.
+      #
+      # The template syntax is deliberately made as minimal as possible, and
+      # only supports the following:
+      #
+      # * Printing a value
+      # * Iterating over collections
+      # * if/else
+      #
+      # The syntax looks as follows:
+      #
+      #     {% each users %}
+      #
+      #     Name: {{user}}
+      #     Likes cats: {% if likes_cats %}yes{% else %}no{% end %}
+      #
+      #     {% end %}
+      #
+      # Newlines can be escaped by ending a line with a backslash. So this:
+      #
+      #     foo \
+      #     bar
+      #
+      # Is the same as this:
+      #
+      #     foo bar
+      #
+      # Templates are compiled into ERB templates, while taking care to make
+      # sure the user can't run arbitrary code. By using ERB we can let it do
+      # the heavy lifting of rendering data; all we need to provide is a
+      # translation layer.
+      #
+      # # Security
+      #
+      # The template syntax this compiler exposes is safe to be used by
+      # untrusted users. Not only are they unable to run arbitrary code, the
+      # compiler also enforces a limit on the integer sizes and the number of
+      # nested loops. ERB tags added by the user are also disabled.
+      class Compiler
+        # A pattern to match a single integer, with an upper size limit.
+        #
+        # We enforce a limit of 10 digits (= a 32 bits integer) so users can't
+        # trigger the allocation of infinitely large bignums, or trigger
+        # RangeError errors when using such integers to access an array value.
+        INTEGER = /^\d{1,10}$/.freeze
+
+        # The name/path of a variable, such as `user.address.city`.
+        #
+        # It's important that this regular expression _doesn't_ allow for
+        # anything but letters, numbers, and underscores, otherwise a user may
+        # use those to "escape" our template and run arbirtary Ruby code. For
+        # example, take this variable:
+        #
+        #     {{') ::Kernel.exit #'}}
+        #
+        # This would then be compiled into:
+        #
+        #     <%= read(variables, '') ::Kernel.exit #'') %>
+        #
+        # Restricting the allowed characters makes this impossible.
+        VAR_NAME = /([\w\.]+)/.freeze
+
+        # A variable tag, such as `{{username}}`.
+        VAR = /{{ \s* #{VAR_NAME} \s* }}/x.freeze
+
+        # The opening tag for a statement.
+        STM_START = /{% \s*/x.freeze
+
+        # The closing tag for a statement.
+        STM_END = /\s* %}/x.freeze
+
+        # A regular `end` closing tag.
+        NORMAL_END = /#{STM_START} end #{STM_END}/x.freeze
+
+        # An `end` closing tag on its own line, without any non-whitespace
+        # preceding or following it.
+        #
+        # These tags need some special care to make it easier to control
+        # whitespace.
+        LONELY_END = /^\s*#{NORMAL_END}\s$/x.freeze
+
+        # An `else` tag.
+        ELSE = /#{STM_START} else #{STM_END}/x.freeze
+
+        # The start of an `each` tag.
+        EACH = /#{STM_START} each \s+ #{VAR_NAME} #{STM_END}/x.freeze
+
+        # The start of an `if` tag.
+        IF = /#{STM_START} if \s+ #{VAR_NAME} #{STM_END}/x.freeze
+
+        # The pattern to use for escaping newlines.
+        ESCAPED_NEWLINE = /\\\n$/.freeze
+
+        # The start tag for ERB tags. These tags will be escaped, preventing
+        # users FROM USING erb DIRECTLY.
+        ERB_START_TAG = '<%'
+
+        def compile(template)
+          transformed_lines = ['<% it = variables %>']
+
+          template.each_line { |line| transformed_lines << transform(line) }
+          Template.new(transformed_lines.join)
+        end
+
+        def transform(line)
+          line.gsub!(ESCAPED_NEWLINE, '')
+          line.gsub!(ERB_START_TAG, '<%%')
+
+          # This replacement ensures that "end" blocks on their own lines
+          # don't add extra newlines. Using an ERB -%> tag sadly swallows too
+          # many newlines.
+          line.gsub!(LONELY_END, '<% end %>')
+          line.gsub!(NORMAL_END, '<% end %>')
+          line.gsub!(ELSE, '<% else -%>')
+
+          line.gsub!(EACH) do
+            # No, `it; variables` isn't a syntax error. Using `;` marks
+            # `variables` as block-local, making it possible to re-assign it
+            # without affecting outer definitions of this variable. We use
+            # this to scope template variables to the right input Hash.
+            "<% each(#{read_path(Regexp.last_match(1))}) do |it; variables| -%><% variables = it -%>"
+          end
+
+          line.gsub!(IF) { "<% if truthy?(#{read_path(Regexp.last_match(1))}) -%>" }
+          line.gsub!(VAR) { "<%= #{read_path(Regexp.last_match(1))} %>" }
+          line
+        end
+
+        def read_path(path)
+          return path if path == 'it'
+
+          args = path.split('.')
+          args.map! { |arg| arg.match?(INTEGER) ? "#{arg}" : "'#{arg}'" }
+
+          "read(variables, #{args.join(', ')})"
+        end
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/changelog/template/context.rb b/lib/gitlab/changelog/template/context.rb
new file mode 100644
index 0000000000000000000000000000000000000000..8a0796d767e2b14ff8d327c5a7ff1acc3a448eb5
--- /dev/null
+++ b/lib/gitlab/changelog/template/context.rb
@@ -0,0 +1,70 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    module Template
+      # Context is used to provide a binding/context to ERB templates used for
+      # rendering changelogs.
+      #
+      # This class extends BasicObject so that we only expose the bare minimum
+      # needed to render the ERB template.
+      class Context < BasicObject
+        MAX_NESTED_LOOPS = 4
+
+        def initialize(variables)
+          @variables = variables
+          @loop_nesting = 0
+        end
+
+        def get_binding
+          ::Kernel.binding
+        end
+
+        def each(value, &block)
+          max = MAX_NESTED_LOOPS
+
+          if @loop_nesting == max
+            ::Kernel.raise(
+              ::Template::TemplateError.new("You can only nest up to #{max} loops")
+            )
+          end
+
+          @loop_nesting += 1
+          result = value.each(&block) if value.respond_to?(:each)
+          @loop_nesting -= 1
+
+          result
+        end
+
+        # rubocop: disable Style/TrivialAccessors
+        def variables
+          @variables
+        end
+        # rubocop: enable Style/TrivialAccessors
+
+        def read(source, *steps)
+          current = source
+
+          steps.each do |step|
+            case current
+            when ::Hash
+              current = current[step]
+            when ::Array
+              return '' unless step.is_a?(::Integer)
+
+              current = current[step]
+            else
+              break
+            end
+          end
+
+          current
+        end
+
+        def truthy?(value)
+          value.respond_to?(:any?) ? value.any? : !!value
+        end
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/changelog/template/template.rb b/lib/gitlab/changelog/template/template.rb
new file mode 100644
index 0000000000000000000000000000000000000000..0ff2852d6d486db0acb998373194a90c9f94a9be
--- /dev/null
+++ b/lib/gitlab/changelog/template/template.rb
@@ -0,0 +1,29 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module Changelog
+    module Template
+      # A wrapper around an ERB template user for rendering changelogs.
+      class Template
+        TemplateError = Class.new(StandardError)
+
+        def initialize(erb)
+          # Don't change the trim mode, as this may require changes to the
+          # regular expressions used to turn the template syntax into ERB
+          # tags.
+          @erb = ERB.new(erb, trim_mode: '-')
+        end
+
+        def render(data)
+          context = Context.new(data).get_binding
+
+          # ERB produces a SyntaxError when processing templates, as it
+          # internally uses eval() for this.
+          @erb.result(context)
+        rescue SyntaxError
+          raise TemplateError.new("The template's syntax is invalid")
+        end
+      end
+    end
+  end
+end
diff --git a/spec/lib/gitlab/changelog/committer_spec.rb b/spec/lib/gitlab/changelog/committer_spec.rb
new file mode 100644
index 0000000000000000000000000000000000000000..71a80264f29d4974baa71ea076e3388b9b9363df
--- /dev/null
+++ b/spec/lib/gitlab/changelog/committer_spec.rb
@@ -0,0 +1,90 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::Changelog::Committer do
+  let(:project) { create(:project, :repository) }
+  let(:user) { project.creator }
+  let(:committer) { described_class.new(project, user) }
+  let(:config) { Gitlab::Changelog::Config.new(project) }
+
+  describe '#commit' do
+    context "when the release isn't in the changelog" do
+      it 'commits the changes' do
+        release = Gitlab::Changelog::Release
+          .new(version: '1.0.0', date: Time.utc(2020, 1, 1), config: config)
+
+        committer.commit(
+          release: release,
+          file: 'CHANGELOG.md',
+          branch: 'master',
+          message: 'Test commit'
+        )
+
+        content = project.repository.blob_at('master', 'CHANGELOG.md').data
+
+        expect(content).to eq(<<~MARKDOWN)
+          ## 1.0.0 (2020-01-01)
+
+          No changes.
+        MARKDOWN
+      end
+    end
+
+    context 'when the release is already in the changelog' do
+      it "doesn't commit the changes" do
+        release = Gitlab::Changelog::Release
+          .new(version: '1.0.0', date: Time.utc(2020, 1, 1), config: config)
+
+        2.times do
+          committer.commit(
+            release: release,
+            file: 'CHANGELOG.md',
+            branch: 'master',
+            message: 'Test commit'
+          )
+        end
+
+        content = project.repository.blob_at('master', 'CHANGELOG.md').data
+
+        expect(content).to eq(<<~MARKDOWN)
+          ## 1.0.0 (2020-01-01)
+
+          No changes.
+        MARKDOWN
+      end
+    end
+
+    context 'when committing the changes fails' do
+      it 'retries the operation' do
+        release = Gitlab::Changelog::Release
+          .new(version: '1.0.0', date: Time.utc(2020, 1, 1), config: config)
+
+        service = instance_spy(Files::MultiService)
+        errored = false
+
+        allow(Files::MultiService)
+          .to receive(:new)
+          .and_return(service)
+
+        allow(service).to receive(:execute) do
+          if errored
+            { status: :success }
+          else
+            errored = true
+            { status: :error }
+          end
+        end
+
+        expect do
+          committer.commit(
+            release: release,
+            file: 'CHANGELOG.md',
+            branch: 'master',
+            message: 'Test commit'
+          )
+        end.not_to raise_error
+      end
+    end
+  end
+end
diff --git a/spec/lib/gitlab/changelog/config_spec.rb b/spec/lib/gitlab/changelog/config_spec.rb
new file mode 100644
index 0000000000000000000000000000000000000000..adf82fa3ac201aa26f52f0050a213c45d191af85
--- /dev/null
+++ b/spec/lib/gitlab/changelog/config_spec.rb
@@ -0,0 +1,96 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::Changelog::Config do
+  let(:project) { build_stubbed(:project) }
+
+  describe '.from_git' do
+    it 'retrieves the configuration from Git' do
+      allow(project.repository)
+        .to receive(:changelog_config)
+        .and_return("---\ndate_format: '%Y'")
+
+      expect(described_class)
+        .to receive(:from_hash)
+        .with(project, 'date_format' => '%Y')
+
+      described_class.from_git(project)
+    end
+
+    it 'returns the default configuration when no YAML file exists in Git' do
+      allow(project.repository)
+        .to receive(:changelog_config)
+        .and_return(nil)
+
+      expect(described_class)
+        .to receive(:new)
+        .with(project)
+
+      described_class.from_git(project)
+    end
+  end
+
+  describe '.from_hash' do
+    it 'sets the configuration according to a Hash' do
+      config = described_class.from_hash(
+        project,
+        'date_format' => 'foo',
+        'template' => 'bar',
+        'categories' => { 'foo' => 'bar' }
+      )
+
+      expect(config.date_format).to eq('foo')
+      expect(config.template).to be_instance_of(Gitlab::Changelog::Template::Template)
+      expect(config.categories).to eq({ 'foo' => 'bar' })
+    end
+
+    it 'raises ConfigError when the categories are not a Hash' do
+      expect { described_class.from_hash(project, 'categories' => 10) }
+        .to raise_error(described_class::ConfigError)
+    end
+  end
+
+  describe '#contributor?' do
+    it 'returns true if a user is a contributor' do
+      user = build_stubbed(:author)
+
+      allow(project.team).to receive(:contributor?).with(user).and_return(true)
+
+      expect(described_class.new(project).contributor?(user)).to eq(true)
+    end
+
+    it "returns true if a user isn't a contributor" do
+      user = build_stubbed(:author)
+
+      allow(project.team).to receive(:contributor?).with(user).and_return(false)
+
+      expect(described_class.new(project).contributor?(user)).to eq(false)
+    end
+  end
+
+  describe '#category' do
+    it 'returns the name of a category' do
+      config = described_class.new(project)
+
+      config.categories['foo'] = 'Foo'
+
+      expect(config.category('foo')).to eq('Foo')
+    end
+
+    it 'returns the raw category name when no alternative name is configured' do
+      config = described_class.new(project)
+
+      expect(config.category('bla')).to eq('bla')
+    end
+  end
+
+  describe '#format_date' do
+    it 'formats a date according to the configured date format' do
+      config = described_class.new(project)
+      time = Time.utc(2021, 1, 5)
+
+      expect(config.format_date(time)).to eq('2021-01-05')
+    end
+  end
+end
diff --git a/spec/lib/gitlab/changelog/generator_spec.rb b/spec/lib/gitlab/changelog/generator_spec.rb
new file mode 100644
index 0000000000000000000000000000000000000000..bc4a7c5dd6b93264d39aade57208f0e556e00a18
--- /dev/null
+++ b/spec/lib/gitlab/changelog/generator_spec.rb
@@ -0,0 +1,164 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::Changelog::Generator do
+  describe '#add' do
+    let(:project) { build_stubbed(:project) }
+    let(:author) { build_stubbed(:user) }
+    let(:commit) { build_stubbed(:commit) }
+    let(:config) { Gitlab::Changelog::Config.new(project) }
+
+    it 'generates the Markdown for the first release' do
+      release = Gitlab::Changelog::Release.new(
+        version: '1.0.0',
+        date: Time.utc(2021, 1, 5),
+        config: config
+      )
+
+      release.add_entry(
+        title: 'This is a new change',
+        commit: commit,
+        category: 'added',
+        author: author
+      )
+
+      gen = described_class.new('')
+
+      expect(gen.add(release)).to eq(<<~MARKDOWN)
+        ## 1.0.0 (2021-01-05)
+
+        ### added (1 change)
+
+        - [This is a new change](#{commit.to_reference(full: true)})
+      MARKDOWN
+    end
+
+    it 'generates the Markdown for a newer release' do
+      release = Gitlab::Changelog::Release.new(
+        version: '2.0.0',
+        date: Time.utc(2021, 1, 5),
+        config: config
+      )
+
+      release.add_entry(
+        title: 'This is a new change',
+        commit: commit,
+        category: 'added',
+        author: author
+      )
+
+      gen = described_class.new(<<~MARKDOWN)
+        This is a changelog file.
+
+        ## 1.0.0
+
+        This is the changelog for version 1.0.0.
+      MARKDOWN
+
+      expect(gen.add(release)).to eq(<<~MARKDOWN)
+        This is a changelog file.
+
+        ## 2.0.0 (2021-01-05)
+
+        ### added (1 change)
+
+        - [This is a new change](#{commit.to_reference(full: true)})
+
+        ## 1.0.0
+
+        This is the changelog for version 1.0.0.
+      MARKDOWN
+    end
+
+    it 'generates the Markdown for a patch release' do
+      release = Gitlab::Changelog::Release.new(
+        version: '1.1.0',
+        date: Time.utc(2021, 1, 5),
+        config: config
+      )
+
+      release.add_entry(
+        title: 'This is a new change',
+        commit: commit,
+        category: 'added',
+        author: author
+      )
+
+      gen = described_class.new(<<~MARKDOWN)
+        This is a changelog file.
+
+        ## 2.0.0
+
+        This is another release.
+
+        ## 1.0.0
+
+        This is the changelog for version 1.0.0.
+      MARKDOWN
+
+      expect(gen.add(release)).to eq(<<~MARKDOWN)
+        This is a changelog file.
+
+        ## 2.0.0
+
+        This is another release.
+
+        ## 1.1.0 (2021-01-05)
+
+        ### added (1 change)
+
+        - [This is a new change](#{commit.to_reference(full: true)})
+
+        ## 1.0.0
+
+        This is the changelog for version 1.0.0.
+      MARKDOWN
+    end
+
+    it 'generates the Markdown for an old release' do
+      release = Gitlab::Changelog::Release.new(
+        version: '0.5.0',
+        date: Time.utc(2021, 1, 5),
+        config: config
+      )
+
+      release.add_entry(
+        title: 'This is a new change',
+        commit: commit,
+        category: 'added',
+        author: author
+      )
+
+      gen = described_class.new(<<~MARKDOWN)
+        This is a changelog file.
+
+        ## 2.0.0
+
+        This is another release.
+
+        ## 1.0.0
+
+        This is the changelog for version 1.0.0.
+      MARKDOWN
+
+      expect(gen.add(release)).to eq(<<~MARKDOWN)
+        This is a changelog file.
+
+        ## 2.0.0
+
+        This is another release.
+
+        ## 1.0.0
+
+        This is the changelog for version 1.0.0.
+
+        ## 0.5.0 (2021-01-05)
+
+        ### added (1 change)
+
+        - [This is a new change](#{commit.to_reference(full: true)})
+      MARKDOWN
+    end
+  end
+end
diff --git a/spec/lib/gitlab/changelog/release_spec.rb b/spec/lib/gitlab/changelog/release_spec.rb
new file mode 100644
index 0000000000000000000000000000000000000000..50a23d23299300c6b7c2930ce141c5586a436e4e
--- /dev/null
+++ b/spec/lib/gitlab/changelog/release_spec.rb
@@ -0,0 +1,107 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::Changelog::Release do
+  describe '#to_markdown' do
+    let(:config) { Gitlab::Changelog::Config.new(build_stubbed(:project)) }
+    let(:commit) { build_stubbed(:commit) }
+    let(:author) { build_stubbed(:user) }
+    let(:mr) { build_stubbed(:merge_request) }
+    let(:release) do
+      described_class
+        .new(version: '1.0.0', date: Time.utc(2021, 1, 5), config: config)
+    end
+
+    context 'when there are no entries' do
+      it 'includes a notice about the lack of entries' do
+        expect(release.to_markdown).to eq(<<~OUT)
+          ## 1.0.0 (2021-01-05)
+
+          No changes.
+
+        OUT
+      end
+    end
+
+    context 'when all data is present' do
+      it 'includes all data' do
+        allow(config).to receive(:contributor?).with(author).and_return(true)
+
+        release.add_entry(
+          title: 'Entry title',
+          commit: commit,
+          category: 'fixed',
+          author: author,
+          merge_request: mr
+        )
+
+        expect(release.to_markdown).to eq(<<~OUT)
+          ## 1.0.0 (2021-01-05)
+
+          ### fixed (1 change)
+
+          - [Entry title](#{commit.to_reference(full: true)}) \
+          by #{author.to_reference(full: true)} \
+          ([merge request](#{mr.to_reference(full: true)}))
+
+        OUT
+      end
+    end
+
+    context 'when no merge request is present' do
+      it "doesn't include a merge request link" do
+        allow(config).to receive(:contributor?).with(author).and_return(true)
+
+        release.add_entry(
+          title: 'Entry title',
+          commit: commit,
+          category: 'fixed',
+          author: author
+        )
+
+        expect(release.to_markdown).to eq(<<~OUT)
+          ## 1.0.0 (2021-01-05)
+
+          ### fixed (1 change)
+
+          - [Entry title](#{commit.to_reference(full: true)}) \
+          by #{author.to_reference(full: true)}
+
+        OUT
+      end
+    end
+
+    context 'when the author is not a contributor' do
+      it "doesn't include the author" do
+        allow(config).to receive(:contributor?).with(author).and_return(false)
+
+        release.add_entry(
+          title: 'Entry title',
+          commit: commit,
+          category: 'fixed',
+          author: author
+        )
+
+        expect(release.to_markdown).to eq(<<~OUT)
+          ## 1.0.0 (2021-01-05)
+
+          ### fixed (1 change)
+
+          - [Entry title](#{commit.to_reference(full: true)})
+
+        OUT
+      end
+    end
+  end
+
+  describe '#header_start_position' do
+    it 'returns a regular expression for finding the start of a release section' do
+      config = Gitlab::Changelog::Config.new(build_stubbed(:project))
+      release = described_class
+        .new(version: '1.0.0', date: Time.utc(2021, 1, 5), config: config)
+
+      expect(release.header_start_pattern).to eq(/^##\s*1\.0\.0/)
+    end
+  end
+end
diff --git a/spec/lib/gitlab/changelog/template/compiler_spec.rb b/spec/lib/gitlab/changelog/template/compiler_spec.rb
new file mode 100644
index 0000000000000000000000000000000000000000..d940fbaec89e5230ed371d2306ee45dafd1849a9
--- /dev/null
+++ b/spec/lib/gitlab/changelog/template/compiler_spec.rb
@@ -0,0 +1,129 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::Changelog::Template::Compiler do
+  def compile(template, data = {})
+    Gitlab::Changelog::Template::Compiler.new.compile(template).render(data)
+  end
+
+  describe '#compile' do
+    it 'compiles an empty template' do
+      expect(compile('')).to eq('')
+    end
+
+    it 'compiles a template with an undefined variable' do
+      expect(compile('{{number}}')).to eq('')
+    end
+
+    it 'compiles a template with a defined variable' do
+      expect(compile('{{number}}', 'number' => 42)).to eq('42')
+    end
+
+    it 'compiles a template with the special "it" variable' do
+      expect(compile('{{it}}', 'values' => 10)).to eq({ 'values' => 10 }.to_s)
+    end
+
+    it 'compiles a template containing an if statement' do
+      expect(compile('{% if foo %}yes{% end %}', 'foo' => true)).to eq('yes')
+    end
+
+    it 'compiles a template containing an if/else statement' do
+      expect(compile('{% if foo %}yes{% else %}no{% end %}', 'foo' => false))
+        .to eq('no')
+    end
+
+    it 'compiles a template that iterates over an Array' do
+      expect(compile('{% each numbers %}{{it}}{% end %}', 'numbers' => [1, 2, 3]))
+        .to eq('123')
+    end
+
+    it 'compiles a template that iterates over a Hash' do
+      output = compile(
+        '{% each pairs %}{{0}}={{1}}{% end %}',
+        'pairs' => { 'key' => 'value' }
+      )
+
+      expect(output).to eq('key=value')
+    end
+
+    it 'compiles a template that iterates over a Hash of Arrays' do
+      output = compile(
+        '{% each values %}{{key}}{% end %}',
+        'values' => [{ 'key' => 'value' }]
+      )
+
+      expect(output).to eq('value')
+    end
+
+    it 'compiles a template with a variable path' do
+      output = compile('{{foo.bar}}', 'foo' => { 'bar' => 10 })
+
+      expect(output).to eq('10')
+    end
+
+    it 'compiles a template with a variable path that uses an Array index' do
+      output = compile('{{foo.values.1}}', 'foo' => { 'values' => [10, 20] })
+
+      expect(output).to eq('20')
+    end
+
+    it 'compiles a template with a variable path that uses a Hash and a numeric index' do
+      output = compile('{{foo.1}}', 'foo' => { 'key' => 'value' })
+
+      expect(output).to eq('')
+    end
+
+    it 'compiles a template with a variable path that uses an Array and a String based index' do
+      output = compile('{{foo.numbers.bla}}', 'foo' => { 'numbers' => [10, 20] })
+
+      expect(output).to eq('')
+    end
+
+    it 'ignores ERB tags provided by the user' do
+      input = '<% exit %> <%= exit %> <%= foo -%>'
+
+      expect(compile(input)).to eq(input)
+    end
+
+    it 'removes newlines introduced by end statements on their own lines' do
+      output = compile(<<~TPL, 'foo' => true)
+        {% if foo %}
+        foo
+        {% end %}
+      TPL
+
+      expect(output).to eq("foo\n")
+    end
+
+    it 'supports escaping of trailing newlines' do
+      output = compile(<<~TPL)
+        foo \
+        bar\
+        baz
+      TPL
+
+      expect(output).to eq("foo barbaz\n")
+    end
+
+    # rubocop: disable Lint/InterpolationCheck
+    it 'ignores embedded Ruby expressions' do
+      input = '#{exit}'
+
+      expect(compile(input)).to eq(input)
+    end
+    # rubocop: enable Lint/InterpolationCheck
+
+    it 'ignores ERB tags inside variable tags' do
+      input = '{{<%= exit %>}}'
+
+      expect(compile(input)).to eq(input)
+    end
+
+    it 'ignores malicious code that tries to escape a variable' do
+      input = "{{') ::Kernel.exit # '}}"
+
+      expect(compile(input)).to eq(input)
+    end
+  end
+end