diff --git a/Makefile b/Makefile
index 4a53fd06153..ad041b48ebc 100644
--- a/Makefile
+++ b/Makefile
@@ -15,7 +15,7 @@ K8S_VERSION = v1.17.2
 REPO = github.com/operator-framework/operator-sdk
 BUILD_PATH = $(REPO)/cmd/operator-sdk
 PKGS = $(shell go list ./... | grep -v /vendor/)
-TEST_PKGS = $(shell go list ./... | grep -v -E 'github.com/operator-framework/operator-sdk/(hack/|test/)')
+TEST_PKGS = $(shell go list ./... | grep -v -E 'github.com/operator-framework/operator-sdk/test/')
 SOURCES = $(shell find . -name '*.go' -not -path "*/vendor/*")
 
 ANSIBLE_BASE_IMAGE = quay.io/operator-framework/ansible-operator
@@ -98,6 +98,9 @@ gen-cli-doc: ## Generate CLI documentation
 gen-test-framework: build/operator-sdk ## Run generate commands to update test/test-framework
 	./hack/generate/gen-test-framework.sh
 
+gen-changelog: ## Generate CHANGELOG.md and migration guide updates
+	./hack/generate/gen-changelog.sh
+
 generate: gen-cli-doc gen-test-framework  ## Run all generate targets
 .PHONY: generate gen-cli-doc gen-test-framework
 
diff --git a/changelog/fragments/00-template.yaml b/changelog/fragments/00-template.yaml
new file mode 100644
index 00000000000..44f68b5ba65
--- /dev/null
+++ b/changelog/fragments/00-template.yaml
@@ -0,0 +1,36 @@
+# entries is a list of entries to include in
+# release notes and/or the migration guide
+entries:
+  - description: >
+      Description is the line that shows up in the CHANGELOG. This
+      should be formatted as markdown and be on a single line. Using
+      the YAML string '>' operator means you can write your entry
+      multiple lines and it will still be parsed as a single line.
+
+    # kind is one of:
+    # - addition
+    # - change
+    # - deprecation
+    # - removal
+    # - bugfix
+    kind: ""
+
+    # Is this a breaking change?
+    breaking: false
+
+    # NOTE: ONLY USE `pull_request_override` WHEN ADDING THIS
+    # FILE FOR A PREVIOUSLY MERGED PULL_REQUEST!
+    #
+    # The generator auto-detects the PR number from the commit
+    # message in which this file was originally added.
+    #
+    # What is the pull request number (without the "#")?
+    # pull_request_override: 0
+
+
+    # Migration can be defined to automatically add a section to
+    # the migration guide. This is required for breaking changes.
+    migration:
+      header: Header text for the migration section
+      body: >
+        Body of the migration section.
diff --git a/doc/dev/release.md b/doc/dev/release.md
index 243c4f8f8b0..4631ac02290 100644
--- a/doc/dev/release.md
+++ b/doc/dev/release.md
@@ -2,7 +2,7 @@
 
 Making an Operator SDK release involves:
 
-- Updating `CHANGELOG.md`.
+- Updating `CHANGELOG.md` and migration guide.
 - Tagging and signing a git commit and pushing the tag to GitHub.
 - Building a release binary and signing the binary
 - Creating a release by uploading binary, signature, and `CHANGELOG.md` updates for the release to GitHub.
@@ -193,7 +193,7 @@ $ git push origin release-v1.3.1
 
 Create a PR from `release-v1.3.1` to `v1.3.x`. Once CI passes and your PR is merged, continue to step 1.
 
-### 1. Create a PR for release version and CHANGELOG.md updates
+### 1. Create a PR for release version, CHANGELOG.md, and migration guide updates
 
 Once all PR's needed for a release have been merged, branch from `master`:
 
@@ -215,14 +215,22 @@ Create a new branch to push release commits:
 $ git checkout -b release-v1.3.0
 ```
 
+Run the CHANGELOG and migration guide generator:
+
+```sh
+$ GEN_CHANGELOG_TAG=v1.3.0 make gen-changelog
+```
+
 Commit the following changes:
 
 - `version/version.go`: update `Version` to `v1.3.0`.
 - `internal/scaffold/go_mod.go`, change the `require` line version for `github.com/operator-framework/operator-sdk` from `master` to `v1.3.0`.
 - `internal/scaffold/helm/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
 - `internal/scaffold/ansible/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
-- `CHANGELOG.md`: update the `## Unreleased` header to `## v1.3.0`.
 - `doc/user/install-operator-sdk.md`: update the linux and macOS URLs to point to the new release URLs.
+- `CHANGELOG.md`: commit changes (updated by changelog generation).
+- `website/content/en/docs/migration/v1.3.0.md`: commit changes (created by changelog generation).
+- `changelog/fragments/*`: commit deleted fragment files (deleted by changelog generation).
 
 _(Non-patch releases only)_ Lock down the master branch to prevent further commits between this and step 4. See [this section](#locking-down-branches) for steps to do so.
 
@@ -254,7 +262,7 @@ Once this tag passes CI, go to step 3. For more info on tagging, see the [releas
 
 **Note:** If CI fails for some reason, you will have to revert the tagged commit, re-commit, and make a new PR.
 
-### 3. Create a PR for post-release version and CHANGELOG.md updates
+### 3. Create a PR for post-release version updates
 
 Check out a new branch from master (or use your `release-v1.3.0` branch) and commit the following changes:
 
@@ -262,21 +270,6 @@ Check out a new branch from master (or use your `release-v1.3.0` branch) and com
 - `internal/scaffold/go_mod.go`, change the `require` line version for `github.com/operator-framework/operator-sdk` from `v1.3.0` to `master`.
 - `internal/scaffold/helm/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
 - `internal/scaffold/ansible/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
-- `CHANGELOG.md`: add the following as a new set of headers above `## v1.3.0`:
-
-    ```markdown
-    ## Unreleased
-
-    ### Added
-
-    ### Changed
-
-    ### Deprecated
-
-    ### Removed
-
-    ### Bug Fixes
-    ```
 
 Create a new PR for this branch, targetting the `master` branch. Once this PR passes CI and is merged, `master` can be unfrozen.
 
diff --git a/hack/generate/changelog/gen-changelog.go b/hack/generate/changelog/gen-changelog.go
new file mode 100644
index 00000000000..fcdf4de705c
--- /dev/null
+++ b/hack/generate/changelog/gen-changelog.go
@@ -0,0 +1,73 @@
+package main
+
+import (
+	"flag"
+	"fmt"
+	"path/filepath"
+	"strings"
+
+	"github.com/blang/semver"
+	log "github.com/sirupsen/logrus"
+
+	"github.com/operator-framework/operator-sdk/hack/generate/changelog/util"
+)
+
+const repo = "github.com/operator-framework/operator-sdk"
+
+func main() {
+	var (
+		tag           string
+		fragmentsDir  string
+		changelogFile string
+		migrationDir  string
+		validateOnly  bool
+	)
+
+	flag.StringVar(&tag, "tag", "",
+		"Title for generated CHANGELOG and migration guide sections")
+	flag.StringVar(&fragmentsDir, "fragments-dir", filepath.Join("changelog", "fragments"),
+		"Path to changelog fragments directory")
+	flag.StringVar(&changelogFile, "changelog", "CHANGELOG.md",
+		"Path to CHANGELOG")
+	flag.StringVar(&migrationDir, "migration-guide-dir",
+		filepath.Join("website", "content", "en", "docs", "migration"),
+		"Path to migration guide directory")
+	flag.BoolVar(&validateOnly, "validate-only", false,
+		"Only validate fragments")
+	flag.Parse()
+
+	if tag == "" && !validateOnly {
+		log.Fatalf("flag '-tag' is required without '-validate-only'")
+	}
+
+	entries, err := util.LoadEntries(fragmentsDir, repo)
+	if err != nil {
+		log.Fatalf("failed to load fragments: %v", err)
+	}
+	if len(entries) == 0 {
+		log.Warnf("no entries found")
+	}
+
+	if validateOnly {
+		return
+	}
+
+	version, err := semver.Parse(strings.TrimPrefix(tag, "v"))
+	if err != nil {
+		log.Fatalf("flag '-tag' is not a valid semantic version: %v", err)
+	}
+	if len(version.Pre) > 0 || len(version.Build) > 0 {
+		log.Fatalf("flag '-tag' must not include a build number or pre-release identifiers")
+	}
+
+	cl := util.ChangelogFromEntries(version, entries)
+	if err := cl.WriteFile(changelogFile); err != nil {
+		log.Fatalf("failed to update CHANGELOG: %v", err)
+	}
+
+	mg := util.MigrationGuideFromEntries(version, entries)
+	mgFile := filepath.Join(migrationDir, fmt.Sprintf("v%s.md", version))
+	if err := mg.WriteFile(mgFile); err != nil {
+		log.Fatalf("failed to create migration guide: %v", err)
+	}
+}
diff --git a/hack/generate/changelog/gen-changelog.sh b/hack/generate/changelog/gen-changelog.sh
new file mode 100755
index 00000000000..f208cb400a8
--- /dev/null
+++ b/hack/generate/changelog/gen-changelog.sh
@@ -0,0 +1,9 @@
+#!/bin/bash
+
+source ./hack/lib/common.sh
+set -e
+shopt -s extglob
+
+[[ -n "$GEN_CHANGELOG_TAG" ]] || fatal "Must set GEN_CHANGELOG_TAG (e.g. export GEN_CHANGELOG_TAG=v1.2.3)"
+go run ./hack/generate/changelog/gen-changelog.go -tag="${GEN_CHANGELOG_TAG}"
+rm ./changelog/fragments/!(00-template.yaml)
diff --git a/hack/generate/changelog/util/changelog.go b/hack/generate/changelog/util/changelog.go
new file mode 100644
index 00000000000..b04d8fca164
--- /dev/null
+++ b/hack/generate/changelog/util/changelog.go
@@ -0,0 +1,129 @@
+package util
+
+import (
+	"bytes"
+	"errors"
+	"fmt"
+	"io/ioutil"
+	"os"
+	"strings"
+	"text/template"
+
+	"github.com/blang/semver"
+)
+
+type Changelog struct {
+	Version      string
+	Additions    []ChangelogEntry
+	Changes      []ChangelogEntry
+	Removals     []ChangelogEntry
+	Deprecations []ChangelogEntry
+	Bugfixes     []ChangelogEntry
+
+	Repo string
+}
+
+type ChangelogEntry struct {
+	Description string
+	Link        string
+}
+
+const changelogTemplate = `## {{ .Version }}
+{{- if or .Additions .Changes .Removals .Deprecations .Bugfixes -}}
+{{- with .Additions }}
+
+### Additions
+{{ range . }}
+- {{ .Description }}{{ if .Link }} ({{ .Link }}){{ end }}
+{{- end }}{{- end }}
+{{- with .Changes }}
+
+### Changes
+{{ range . }}
+- {{ .Description }}{{ if .Link }} ({{ .Link }}){{ end }}
+{{- end }}{{- end }}
+{{- with .Removals }}
+
+### Removals
+{{ range . }}
+- {{ .Description }}{{ if .Link }} ({{ .Link }}){{ end }}
+{{- end }}{{- end }}
+{{- with .Deprecations }}
+
+### Deprecations
+{{ range . }}
+- {{ .Description }}{{ if .Link }} ({{ .Link }}){{ end }}
+{{- end }}{{- end }}
+{{- with .Bugfixes }}
+
+### Bug Fixes
+{{ range . }}
+- {{ .Description }}{{ if .Link }} ({{ .Link }}){{ end }}
+{{- end }}{{- end }}{{- else }}
+
+No changes for this release!{{ end }}
+`
+
+var changelogTmpl = template.Must(template.New("changelog").Parse(changelogTemplate))
+
+func (c *Changelog) Template() ([]byte, error) {
+	w := &bytes.Buffer{}
+	if err := changelogTmpl.Execute(w, c); err != nil {
+		return nil, err
+	}
+	return w.Bytes(), nil
+}
+
+func (c *Changelog) WriteFile(path string) error {
+	data, err := c.Template()
+	if err != nil {
+		return err
+	}
+	existingFile, err := ioutil.ReadFile(path)
+	if err != nil && !errors.Is(err, os.ErrNotExist) {
+		return err
+	}
+	if errors.Is(err, os.ErrNotExist) || len(existingFile) == 0 {
+		return ioutil.WriteFile(path, data, 0644)
+	}
+
+	data = append(data, '\n')
+	data = append(data, existingFile...)
+	return ioutil.WriteFile(path, data, 0644)
+}
+
+func ChangelogFromEntries(version semver.Version, entries []FragmentEntry) Changelog {
+	cl := Changelog{
+		Version: fmt.Sprintf("v%s", version),
+	}
+	for _, e := range entries {
+		cle := e.toChangelogEntry()
+		switch e.Kind {
+		case Addition:
+			cl.Additions = append(cl.Additions, cle)
+		case Change:
+			cl.Changes = append(cl.Changes, cle)
+		case Removal:
+			cl.Removals = append(cl.Removals, cle)
+		case Deprecation:
+			cl.Deprecations = append(cl.Deprecations, cle)
+		case Bugfix:
+			cl.Bugfixes = append(cl.Bugfixes, cle)
+		}
+	}
+	return cl
+}
+
+func (e *FragmentEntry) toChangelogEntry() ChangelogEntry {
+	cle := ChangelogEntry{}
+	desc := strings.TrimSpace(e.Description)
+	if e.Breaking {
+		desc = fmt.Sprintf("**Breaking change**: %s", desc)
+	}
+	if !strings.HasSuffix(desc, ".") && !strings.HasSuffix(desc, "!") {
+		desc = fmt.Sprintf("%s.", desc)
+	}
+	cle.Description = desc
+	cle.Link = e.PullRequestLink
+	return cle
+}
diff --git a/hack/generate/changelog/util/changelog_test.go b/hack/generate/changelog/util/changelog_test.go
new file mode 100644
index 00000000000..a5d261a7272
--- /dev/null
+++ b/hack/generate/changelog/util/changelog_test.go
@@ -0,0 +1,536 @@
+package util
+
+import (
+	"fmt"
+	"io/ioutil"
+	"os"
+	"testing"
+
+	"github.com/blang/semver"
+	"github.com/stretchr/testify/assert"
+)
+
+func getChangelogEntries(n int) []ChangelogEntry {
+	entries := make([]ChangelogEntry, n)
+	for i := 0; i < n; i++ {
+		entries[i] = ChangelogEntry{
+			Description: fmt.Sprintf("Changelog entry description %d.", i),
+			Link:        "[#999999](https://example.com/test/changelog/pulls/999999)",
+		}
+	}
+	return entries
+}
+
+func TestChangelog_Template(t *testing.T) {
+	testCases := []struct {
+		name      string
+		changelog Changelog
+		output    string
+	}{
+		{
+			name: "all with 1 entry",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(1),
+				Changes:      getChangelogEntries(1),
+				Removals:     getChangelogEntries(1),
+				Deprecations: getChangelogEntries(1),
+				Bugfixes:     getChangelogEntries(1),
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "all with 2 entries",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(2),
+				Changes:      getChangelogEntries(2),
+				Removals:     getChangelogEntries(2),
+				Deprecations: getChangelogEntries(2),
+				Bugfixes:     getChangelogEntries(2),
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "no additions",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    nil,
+				Changes:      getChangelogEntries(1),
+				Removals:     getChangelogEntries(1),
+				Deprecations: getChangelogEntries(1),
+				Bugfixes:     getChangelogEntries(1),
+			},
+			output: `## v999.999.999
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "no changes",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(1),
+				Changes:      nil,
+				Removals:     getChangelogEntries(1),
+				Deprecations: getChangelogEntries(1),
+				Bugfixes:     getChangelogEntries(1),
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "no removals",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(1),
+				Changes:      getChangelogEntries(1),
+				Removals:     nil,
+				Deprecations: getChangelogEntries(1),
+				Bugfixes:     getChangelogEntries(1),
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "no deprecations",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(1),
+				Changes:      getChangelogEntries(1),
+				Removals:     getChangelogEntries(1),
+				Deprecations: nil,
+				Bugfixes:     getChangelogEntries(1),
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "no bug fixes",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(1),
+				Changes:      getChangelogEntries(1),
+				Removals:     getChangelogEntries(1),
+				Deprecations: getChangelogEntries(1),
+				Bugfixes:     nil,
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "entry with no link",
+			changelog: Changelog{
+				Version: "v999.999.999",
+				Additions: []ChangelogEntry{
+					{
+						Description: "Changelog entry description 0.",
+					},
+					{
+						Description: "Changelog entry description 1.",
+						Link:        "[#999999](https://example.com/test/changelog/pulls/999999)",
+					},
+				},
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0.
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "no entries",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    nil,
+				Changes:      nil,
+				Removals:     nil,
+				Deprecations: nil,
+				Bugfixes:     nil,
+			},
+			output: `## v999.999.999
+
+No changes for this release!
+`,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			d, err := tc.changelog.Template()
+			if err != nil {
+				t.Errorf("Got unexpected error: %v", err)
+			}
+			assert.Equal(t, tc.output, string(d))
+		})
+	}
+}
+
+func TestChangelog_WriteFile(t *testing.T) {
+
+	testCases := []struct {
+		name                 string
+		changelog            Changelog
+		existingFile         bool
+		existingFileContents string
+		output               string
+	}{
+		{
+			name: "non-existent file",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(2),
+				Changes:      getChangelogEntries(2),
+				Removals:     getChangelogEntries(2),
+				Deprecations: getChangelogEntries(2),
+				Bugfixes:     getChangelogEntries(2),
+			},
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "empty file",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(2),
+				Changes:      getChangelogEntries(2),
+				Removals:     getChangelogEntries(2),
+				Deprecations: getChangelogEntries(2),
+				Bugfixes:     getChangelogEntries(2),
+			},
+			existingFile: true,
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+		{
+			name: "existing file",
+			changelog: Changelog{
+				Version:      "v999.999.999",
+				Additions:    getChangelogEntries(2),
+				Changes:      getChangelogEntries(2),
+				Removals:     getChangelogEntries(2),
+				Deprecations: getChangelogEntries(2),
+				Bugfixes:     getChangelogEntries(2),
+			},
+			existingFileContents: `## v999.999.998
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+			output: `## v999.999.999
+
+### Additions
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Changes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Removals
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Deprecations
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+
+## v999.999.998
+
+### Bug Fixes
+
+- Changelog entry description 0. ([#999999](https://example.com/test/changelog/pulls/999999))
+- Changelog entry description 1. ([#999999](https://example.com/test/changelog/pulls/999999))
+`,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			tmpFile, err := ioutil.TempFile("", "go-test-changelog")
+			assert.NoError(t, err)
+			assert.NoError(t, tmpFile.Close())
+			defer assert.NoError(t, os.Remove(tmpFile.Name()))
+
+			if tc.existingFile || len(tc.existingFileContents) > 0 {
+				assert.NoError(t, ioutil.WriteFile(tmpFile.Name(), []byte(tc.existingFileContents), 0644))
+			}
+
+			assert.NoError(t, tc.changelog.WriteFile(tmpFile.Name()))
+
+			d, err := ioutil.ReadFile(tmpFile.Name())
+			assert.NoError(t, err)
+			assert.Equal(t, tc.output, string(d))
+		})
+	}
+}
+
+func TestChangelog_ChangelogFromEntries(t *testing.T) {
+	testCases := []struct {
+		name      string
+		version   semver.Version
+		entries   []FragmentEntry
+		changelog Changelog
+	}{
+		{
+			name:      "no entries",
+			version:   semver.MustParse("999.999.999"),
+			changelog: Changelog{Version: "v999.999.999"},
+		},
+		{
+			name:    "add periods to descriptions and breaking change prefix",
+			version: semver.MustParse("999.999.999"),
+			entries: []FragmentEntry{
+				{
+					Description:     "Changelog entry description 0",
+					Kind:            Addition,
+					Breaking:        false,
+					PullRequestLink: "[#999999](https://example.com/test/changelog/pulls/999999)",
+				},
+				{
+					Description: "Changelog entry description 0",
+					Kind:        Change,
+					Breaking:    true,
+				},
+				{
+					Description: "Changelog entry description 0",
+					Kind:        Removal,
+					Breaking:    true,
+				},
+				{
+					Description: "Changelog entry description 0",
+					Kind:        Deprecation,
+					Breaking:    false,
+				},
+				{
+					Description: "Changelog entry description 0",
+					Kind:        Bugfix,
+					Breaking:    false,
+				},
+			},
+			changelog: Changelog{
+				Version: "v999.999.999",
+				Additions: []ChangelogEntry{
+					{
+						Description: "Changelog entry description 0.",
+						Link:        "[#999999](https://example.com/test/changelog/pulls/999999)",
+					},
+				},
+				Changes: []ChangelogEntry{
+					{
+						Description: "**Breaking change**: Changelog entry description 0.",
+					},
+				},
+				Removals: []ChangelogEntry{
+					{
+						Description: "**Breaking change**: Changelog entry description 0.",
+					},
+				},
+				Deprecations: []ChangelogEntry{
+					{
+						Description: "Changelog entry description 0.",
+					},
+				},
+				Bugfixes: []ChangelogEntry{
+					{
+						Description: "Changelog entry description 0.",
+					},
+				},
+			},
+		},
+	}
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			cl := ChangelogFromEntries(tc.version, tc.entries)
+			assert.Equal(t, tc.changelog, cl)
+		})
+	}
+}
diff --git a/hack/generate/changelog/util/fragment.go b/hack/generate/changelog/util/fragment.go
new file mode 100644
index 00000000000..4a8b28980fe
--- /dev/null
+++ b/hack/generate/changelog/util/fragment.go
@@ -0,0 +1,199 @@
+package util
+
+import (
+	"errors"
+	"fmt"
+	"io/ioutil"
+	"os/exec"
+	"path/filepath"
+	"regexp"
+	"strconv"
+	"strings"
+
+	log "github.com/sirupsen/logrus"
+	"gopkg.in/yaml.v2"
+)
+
+type Fragment struct {
+	Entries []FragmentEntry `yaml:"entries"`
+}
+
+func (f *Fragment) Validate() error {
+	for i, e := range f.Entries {
+		if err := e.Validate(); err != nil {
+			return fmt.Errorf("entry[%d] invalid: %v", i, err)
+		}
+	}
+	return nil
+}
+
+type FragmentEntry struct {
+	Description string          `yaml:"description"`
+	Kind        EntryKind       `yaml:"kind"`
+	Breaking    bool            `yaml:"breaking"`
+	Migration   *EntryMigration `yaml:"migration,omitempty"`
+	PullRequest *uint           `yaml:"pull_request_override,omitempty"`
+
+	PullRequestLink string `yaml:"-"`
+}
+
+func (e *FragmentEntry) Validate() error {
+	if err := e.Kind.Validate(); err != nil {
+		return fmt.Errorf("invalid kind: %v", err)
+	}
+
+	if len(e.Description) == 0 {
+		return errors.New("missing description")
+	}
+
+	if e.Breaking && e.Kind != Change && e.Kind != Removal {
+		return fmt.Errorf("breaking changes can only be kind %q or %q, got %q", Change, Removal, e.Kind)
+	}
+
+	if e.Breaking && e.Migration == nil {
+		return fmt.Errorf("breaking changes require migration sections")
+	}
+
+	if e.Migration != nil {
+		if err := e.Migration.Validate(); err != nil {
+			return fmt.Errorf("invalid migration: %v", err)
+		}
+	}
+	return nil
+}
+
+func (e FragmentEntry) pullRequestLink(repo string) string {
+	if e.PullRequest == nil {
+		return ""
+	}
+	return fmt.Sprintf("[#%d](https://%s/pull/%d)", *e.PullRequest, repo, *e.PullRequest)
+}
+
+type EntryKind string
+
+const (
+	Addition    EntryKind = "addition"
+	Change      EntryKind = "change"
+	Removal     EntryKind = "removal"
+	Deprecation EntryKind = "deprecation"
+	Bugfix      EntryKind = "bugfix"
+)
+
+func (k EntryKind) Validate() error {
+	for _, t := range []EntryKind{Addition, Change, Removal, Deprecation, Bugfix} {
+		if k == t {
+			return nil
+		}
+	}
+	return fmt.Errorf("%q is not a supported kind", k)
+}
+
+type EntryMigration struct {
+	Header string `yaml:"header"`
+	Body   string `yaml:"body"`
+}
+
+func (m EntryMigration) Validate() error {
+	if len(m.Header) == 0 {
+		return errors.New("header not specified")
+	}
+	if len(m.Body) == 0 {
+		return errors.New("body not specified")
+	}
+	return nil
+}
+
+func LoadEntries(fragmentsDir, repo string) ([]FragmentEntry, error) {
+	files, err := ioutil.ReadDir(fragmentsDir)
+	if err != nil {
+		return nil, fmt.Errorf("failed to read fragments directory: %w", err)
+	}
+
+	var entries []FragmentEntry
+	for _, fragFile := range files {
+		if fragFile.Name() == "00-template.yaml" {
+			continue
+		}
+		if fragFile.IsDir() {
+			log.Warnf("Skipping directory %q", fragFile.Name())
+			continue
+		}
+		if filepath.Ext(fragFile.Name()) != ".yaml" {
+			log.Warnf("Skipping non-YAML file %q", fragFile.Name())
+			continue
+		}
+		path := filepath.Join(fragmentsDir, fragFile.Name())
+		fragmentData, err := ioutil.ReadFile(path)
+		if err != nil {
+			return nil, fmt.Errorf("failed to read fragment file %q: %w", fragFile.Name(), err)
+		}
+
+		fragment := Fragment{}
+		if err := yaml.Unmarshal(fragmentData, &fragment); err != nil {
+			return nil, fmt.Errorf("failed to parse fragment file %q: %w", fragFile.Name(), err)
+		}
+
+		if err := fragment.Validate(); err != nil {
+			return nil, fmt.Errorf("failed to validate fragment file %q: %w", fragFile.Name(), err)
+		}
+
+		prNum, err := prGetter.GetPullRequestNumberFor(path)
+		if err != nil {
+			log.Warn(err)
+		}
+
+		if prNum != 0 {
+			for i, e := range fragment.Entries {
+				if e.PullRequest == nil {
+					fragment.Entries[i].PullRequest = &prNum
+				}
+			}
+		}
+
+		for i, e := range fragment.Entries {
+			fragment.Entries[i].PullRequestLink = e.pullRequestLink(repo)
+		}
+
+		entries = append(entries, fragment.Entries...)
+	}
+	return entries, nil
+}
+
+var prGetter PullRequestNumberGetter = &gitPullRequestNumberGetter{}
+
+type PullRequestNumberGetter interface {
+	GetPullRequestNumberFor(file string) (uint, error)
+}
+
+type gitPullRequestNumberGetter struct{}
+
+func (g *gitPullRequestNumberGetter) GetPullRequestNumberFor(filename string) (uint, error) {
+	msg, err := g.getCommitMessage(filename)
+	if err != nil {
+		return 0, err
+	}
+	return g.parsePRNumber(msg)
+}
+
+func (g *gitPullRequestNumberGetter) getCommitMessage(filename string) (string, error) {
+	args := fmt.Sprintf("log --follow --pretty=format:%%s --diff-filter=A --find-renames=40%% %s", filename)
+	line, err := exec.Command("git", strings.Split(args, " ")...).CombinedOutput()
+	if err != nil {
+		return "", fmt.Errorf("failed to locate git commit for PR discovery: %v", err)
+	}
+	return string(line), nil
+}
+
+var numRegex = regexp.MustCompile(`\(#(\d+)\)$`)
+
+func (g *gitPullRequestNumberGetter) parsePRNumber(msg string) (uint, error) {
+	matches := numRegex.FindAllStringSubmatch(msg, 1)
+	if len(matches) == 0 || len(matches[0]) < 2 {
+		return 0, fmt.Errorf("could not find PR number in commit message")
+	}
+	u64, err := strconv.ParseUint(matches[0][1], 10, 64)
+	if err != nil {
+		return 0, fmt.Errorf("failed to parse PR number %q from commit message: %v", matches[0][1], err)
+	}
+	return uint(u64), nil
+}
diff --git a/hack/generate/changelog/util/fragment_test.go b/hack/generate/changelog/util/fragment_test.go
new file mode 100644
index 00000000000..aa299b25554
--- /dev/null
+++ b/hack/generate/changelog/util/fragment_test.go
@@ -0,0 +1,372 @@
+package util
+
+import (
+	"fmt"
+	"strings"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+type mockValidPRGetter struct{}
+
+var _ PullRequestNumberGetter = &mockValidPRGetter{}
+
+func (m *mockValidPRGetter) GetPullRequestNumberFor(file string) (uint, error) {
+	return 999998, nil
+}
+
+func TestFragment_LoadEntries(t *testing.T) {
+	discoveredPRNum := uint(999998)
+	overriddenPRNum := uint(999999)
+	repoLink := "example.com/test/changelog"
+
+	testCases := []struct {
+		name            string
+		fragmentsDir    string
+		prGetter        PullRequestNumberGetter
+		expectedEntries []FragmentEntry
+		expectedErr     string
+	}{
+		{
+			name:            "ignore non-fragments",
+			fragmentsDir:    "testdata/ignore",
+			expectedEntries: nil,
+		},
+		{
+			name:            "invalid yaml",
+			fragmentsDir:    "testdata/invalid_yaml",
+			expectedEntries: nil,
+			expectedErr:     "unmarshal errors",
+		},
+		{
+			name:            "invalid entry",
+			fragmentsDir:    "testdata/invalid_entry",
+			expectedEntries: nil,
+			expectedErr:     `failed to validate fragment file`,
+		},
+		{
+			name:         "valid fragments",
+			fragmentsDir: "testdata/valid",
+			prGetter:     &mockValidPRGetter{},
+			expectedEntries: []FragmentEntry{
+				{
+					Description:     "Addition description 0",
+					Kind:            Addition,
+					PullRequest:     &discoveredPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", discoveredPRNum, repoLink, discoveredPRNum),
+				},
+				{
+					Description:     "Change description 0",
+					Kind:            Change,
+					PullRequest:     &discoveredPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", discoveredPRNum, repoLink, discoveredPRNum),
+				},
+				{
+					Description: "Removal description 0",
+					Kind:        Removal,
+					Breaking:    true,
+					Migration: &EntryMigration{
+						Header: "Header for removal migration 0",
+						Body:   "Body for removal migration 0",
+					},
+					PullRequest:     &discoveredPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", discoveredPRNum, repoLink, discoveredPRNum),
+				},
+				{
+					Description:     "Deprecation description 0",
+					Kind:            Deprecation,
+					PullRequest:     &discoveredPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", discoveredPRNum, repoLink, discoveredPRNum),
+				},
+				{
+					Description:     "Bugfix description 0",
+					Kind:            Bugfix,
+					PullRequest:     &discoveredPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", discoveredPRNum, repoLink, discoveredPRNum),
+				},
+				{
+					Description:     "Addition description 1",
+					Kind:            Addition,
+					PullRequest:     &overriddenPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", overriddenPRNum, repoLink, overriddenPRNum),
+				},
+				{
+					Description:     "Change description 1",
+					Kind:            Change,
+					PullRequest:     &overriddenPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", overriddenPRNum, repoLink, overriddenPRNum),
+				},
+				{
+					Description: "Removal description 1",
+					Kind:        Removal,
+					Breaking:    true,
+					Migration: &EntryMigration{
+						Header: "Header for removal migration 1",
+						Body:   "Body for removal migration 1",
+					},
+					PullRequest:     &overriddenPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", overriddenPRNum, repoLink, overriddenPRNum),
+				},
+				{
+					Description:     "Deprecation description 1",
+					Kind:            Deprecation,
+					PullRequest:     &overriddenPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", overriddenPRNum, repoLink, overriddenPRNum),
+				},
+				{
+					Description:     "Bugfix description 1",
+					Kind:            Bugfix,
+					PullRequest:     &overriddenPRNum,
+					PullRequestLink: fmt.Sprintf("[#%d](https://%s/pull/%d)", overriddenPRNum, repoLink, overriddenPRNum),
+				},
+			},
+		},
+	}
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			prGetter = tc.prGetter
+			entries, err := LoadEntries(tc.fragmentsDir, repoLink)
+			assert.Equal(t, tc.expectedEntries, entries)
+			if len(tc.expectedErr) > 0 {
+				if !strings.Contains(err.Error(), tc.expectedErr) {
+					t.Errorf("expected error to contain: %q, got %q", tc.expectedErr, err)
+				}
+			} else {
+				assert.NoError(t, err)
+			}
+		})
+	}
+}
+
+func TestFragmentEntry_Validate(t *testing.T) {
+	testCases := []struct {
+		name          string
+		fragmentEntry FragmentEntry
+		expectedErr   string
+	}{
+		{
+			name: "invalid kind",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        "invalid",
+				Breaking:    false,
+			},
+			expectedErr: "invalid kind",
+		},
+		{
+			name: "missing description",
+			fragmentEntry: FragmentEntry{
+				Description: "",
+				Kind:        Addition,
+				Breaking:    false,
+			},
+			expectedErr: "missing description",
+		},
+		{
+			name: "breaking addition not allowed",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Addition,
+				Breaking:    true,
+			},
+			expectedErr: `breaking changes can only be kind "change" or "removal", got "addition"`,
+		},
+		{
+			name: "breaking deprecation not allowed",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Deprecation,
+				Breaking:    true,
+			},
+			expectedErr: `breaking changes can only be kind "change" or "removal", got "deprecation"`,
+		},
+		{
+			name: "breaking bugfix not allowed",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Bugfix,
+				Breaking:    true,
+			},
+			expectedErr: `breaking changes can only be kind "change" or "removal", got "bugfix"`,
+		},
+		{
+			name: "migration missing",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Change,
+				Breaking:    true,
+			},
+			expectedErr: `breaking changes require migration sections`,
+		},
+		{
+			name: "migration header missing",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Change,
+				Breaking:    true,
+				Migration: &EntryMigration{
+					Header: "",
+					Body:   "migration body",
+				},
+			},
+			expectedErr: `invalid migration: header not specified`,
+		},
+		{
+			name: "migration body missing",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Change,
+				Breaking:    true,
+				Migration: &EntryMigration{
+					Header: "migration header",
+					Body:   "",
+				},
+			},
+			expectedErr: `invalid migration: body not specified`,
+		},
+		{
+			name: "breaking change allowed",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Change,
+				Breaking:    true,
+				Migration: &EntryMigration{
+					Header: "migration header",
+					Body:   "migration body",
+				},
+			},
+			expectedErr: ``,
+		},
+		{
+			name: "breaking removal allowed",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Removal,
+				Breaking:    true,
+				Migration: &EntryMigration{
+					Header: "migration header",
+					Body:   "migration body",
+				},
+			},
+			expectedErr: ``,
+		},
+		{
+			name: "non-breaking migration allowed",
+			fragmentEntry: FragmentEntry{
+				Description: "description",
+				Kind:        Addition,
+				Breaking:    false,
+				Migration: &EntryMigration{
+					Header: "migration header",
+					Body:   "migration body",
+				},
+			},
+			expectedErr: ``,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			err := tc.fragmentEntry.Validate()
+
+			if len(tc.expectedErr) == 0 {
+				assert.NoError(t, err)
+			} else if err == nil {
+				t.Errorf("expected error to contain %q, got no error", tc.expectedErr)
+			} else {
+				if !strings.Contains(err.Error(), tc.expectedErr) {
+					t.Errorf("expected error to contain: %q, got %q", tc.expectedErr, err)
+				}
+			}
+		})
+	}
+}
+
+func TestFragmentEntry_PullRequestLink(t *testing.T) {
+	prNum := uint(999999)
+	testCases := []struct {
+		name          string
+		fragmentEntry FragmentEntry
+		repo          string
+		link          string
+	}{
+		{
+			name:          "no link",
+			fragmentEntry: FragmentEntry{},
+			link:          "",
+		},
+		{
+			name:          "link with repo 1",
+			repo:          "example.com/test/repo1",
+			fragmentEntry: FragmentEntry{PullRequest: &prNum},
+			link:          "[#999999](https://example.com/test/repo1/pull/999999)",
+		},
+		{
+			name:          "link with repo 2",
+			repo:          "example.com/test/repo2",
+			fragmentEntry: FragmentEntry{PullRequest: &prNum},
+			link:          "[#999999](https://example.com/test/repo2/pull/999999)",
+		},
+	}
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			link := tc.fragmentEntry.pullRequestLink(tc.repo)
+			assert.Equal(t, tc.link, link)
+		})
+	}
+}
+
+func TestGitPullRequestNumberGetter_parsePRNumber(t *testing.T) {
+	prg := &gitPullRequestNumberGetter{}
+	testCases := []struct {
+		name        string
+		msg         string
+		prNum       uint
+		expectedErr string
+	}{
+		{
+			name:  "valid message",
+			msg:   "this is a message with a PR number at the end (#999999)",
+			prNum: uint(999999),
+		},
+		{
+			name:        "missing parentheses",
+			msg:         "this is a message with a PR number at the end #999999",
+			expectedErr: `could not find PR number in commit message`,
+		},
+		{
+			name:        "not at the end",
+			msg:         "this is a message with a PR number (#999999) in the middle",
+			expectedErr: `could not find PR number in commit message`,
+		},
+		{
+			name:        "no PR number",
+			msg:         "this is a message without a PR number",
+			expectedErr: `could not find PR number in commit message`,
+		},
+		{
+			name:        "invalid PR number",
+			msg:         "this is a message with a really big PR number (#99999999999999999999999999999999999999)",
+			expectedErr: `value out of range`,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			prNum, err := prg.parsePRNumber(tc.msg)
+
+			if len(tc.expectedErr) == 0 {
+				assert.NoError(t, err)
+			} else if err == nil {
+				t.Errorf("expected error to contain %q, got no error", tc.expectedErr)
+			} else {
+				if !strings.Contains(err.Error(), tc.expectedErr) {
+					t.Errorf("expected error to contain: %q, got %q", tc.expectedErr, err)
+				}
+			}
+
+			assert.Equal(t, tc.prNum, prNum)
+		})
+	}
+}
diff --git a/hack/generate/changelog/util/migration_guide.go b/hack/generate/changelog/util/migration_guide.go
new file mode 100644
index 00000000000..b123c9df6de
--- /dev/null
+++ b/hack/generate/changelog/util/migration_guide.go
@@ -0,0 +1,77 @@
+package util
+
+import (
+	"bytes"
+	"fmt"
+	"io/ioutil"
+	"strings"
+	"text/template"
+
+	"github.com/blang/semver"
+)
+
+type MigrationGuide struct {
+	Version    string
+	Weight     uint64
+	Migrations []Migration
+}
+
+type Migration struct {
+	Header          string
+	Body            string
+	PullRequestLink string
+}
+
+const migrationGuideTemplate = `---
+title: {{ .Version }}
+weight: {{ .Weight }}
+---
+{{ range .Migrations }}
+## {{ .Header }}
+
+{{ .Body }}
+{{ if .PullRequestLink }}
+_See {{ .PullRequestLink }} for more details._
+{{ end }}{{ else }}
+There are no migrations for this release! :tada:
+{{ end }}`
+
+var migrationGuideTmpl = template.Must(template.New("migrationGuide").Parse(migrationGuideTemplate))
+
+func (mg *MigrationGuide) Template() ([]byte, error) {
+	w := &bytes.Buffer{}
+	if err := migrationGuideTmpl.Execute(w, mg); err != nil {
+		return nil, err
+	}
+	return w.Bytes(), nil
+}
+
+func (mg *MigrationGuide) WriteFile(path string) error {
+	data, err := mg.Template()
+	if err != nil {
+		return err
+	}
+	return ioutil.WriteFile(path, data, 0644)
+}
+
+func MigrationGuideFromEntries(version semver.Version, entries []FragmentEntry) MigrationGuide {
+	mg := MigrationGuide{
+		Version: fmt.Sprintf("v%s", version.String()),
+		Weight:  versionToWeight(version),
+	}
+	for _, e := range entries {
+		if e.Migration == nil {
+			continue
+		}
+		mg.Migrations = append(mg.Migrations, Migration{
+			Header:          e.Migration.Header,
+			Body:            strings.TrimSpace(e.Migration.Body),
+			PullRequestLink: e.PullRequestLink,
+		})
+	}
+	return mg
+}
+
+func versionToWeight(v semver.Version) uint64 {
+	return 1_000_000_000 - (v.Major * 1_000_000) - (v.Minor * 1_000) - v.Patch
+}
diff --git a/hack/generate/changelog/util/migration_guide_test.go b/hack/generate/changelog/util/migration_guide_test.go
new file mode 100644
index 00000000000..3f08b666206
--- /dev/null
+++ b/hack/generate/changelog/util/migration_guide_test.go
@@ -0,0 +1,277 @@
+package util
+
+import (
+	"io/ioutil"
+	"os"
+	"testing"
+
+	"github.com/blang/semver"
+	"github.com/stretchr/testify/assert"
+)
+
+func TestMigrationGuide_Template(t *testing.T) {
+	testCases := []struct {
+		name   string
+		mg     MigrationGuide
+		output string
+	}{
+		{
+			name: "link_then_no_link",
+			mg: MigrationGuide{
+				Version: "v999.999.999",
+				Weight:  1,
+				Migrations: []Migration{
+					{
+						Header:          "Migration header 0",
+						Body:            "Migration body 0",
+						PullRequestLink: "[#999999](https://example.com/test/changelog/pull/999999)",
+					},
+					{
+						Header: "Migration header 1",
+						Body:   "Migration body 1",
+					},
+				},
+			},
+			output: `---
+title: v999.999.999
+weight: 1
+---
+
+## Migration header 0
+
+Migration body 0
+
+_See [#999999](https://example.com/test/changelog/pull/999999) for more details._
+
+## Migration header 1
+
+Migration body 1
+`,
+		},
+		{
+			name: "no_link_then_link",
+			mg: MigrationGuide{
+				Version: "v999.999.999",
+				Weight:  2,
+				Migrations: []Migration{
+					{
+						Header: "Migration header 0",
+						Body:   "Migration body 0",
+					},
+					{
+						Header:          "Migration header 1",
+						Body:            "Migration body 1",
+						PullRequestLink: "[#999999](https://example.com/test/changelog/pull/999999)",
+					},
+				},
+			},
+			output: `---
+title: v999.999.999
+weight: 2
+---
+
+## Migration header 0
+
+Migration body 0
+
+## Migration header 1
+
+Migration body 1
+
+_See [#999999](https://example.com/test/changelog/pull/999999) for more details._
+`,
+		},
+		{
+			name: "no migrations",
+			mg: MigrationGuide{
+				Version: "v999.999.999",
+				Weight:  3,
+			},
+			output: `---
+title: v999.999.999
+weight: 3
+---
+
+There are no migrations for this release! :tada:
+`,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			d, err := tc.mg.Template()
+			if err != nil {
+				t.Errorf("Got unexpected error: %v", err)
+			}
+			assert.Equal(t, tc.output, string(d))
+		})
+	}
+}
+
+func TestMigrationGuide_WriteFile(t *testing.T) {
+
+	testCases := []struct {
+		name   string
+		mg     MigrationGuide
+		output string
+	}{
+		{
+			name: "valid",
+			mg: MigrationGuide{
+				Version: "v999.999.999",
+				Migrations: []Migration{
+					{
+						Header:          "Migration header 0",
+						Body:            "Migration body 0",
+						PullRequestLink: "[#999999](https://example.com/test/changelog/pull/999999)",
+					},
+					{
+						Header: "Migration header 1",
+						Body:   "Migration body 1",
+					},
+				},
+			},
+			output: `---
+title: v999.999.999
+weight: 0
+---
+
+## Migration header 0
+
+Migration body 0
+
+_See [#999999](https://example.com/test/changelog/pull/999999) for more details._
+
+## Migration header 1
+
+Migration body 1
+`,
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			tmpFile, err := ioutil.TempFile("", "go-test-changelog")
+			assert.NoError(t, err)
+			assert.NoError(t, tmpFile.Close())
+			defer assert.NoError(t, os.Remove(tmpFile.Name()))
+
+			assert.NoError(t, tc.mg.WriteFile(tmpFile.Name()))
+
+			d, err := ioutil.ReadFile(tmpFile.Name())
+			assert.NoError(t, err)
+			assert.Equal(t, tc.output, string(d))
+		})
+	}
+}
+
+func TestMigrationGuide_MigrationGuideFromEntries(t *testing.T) {
+	testCases := []struct {
+		name    string
+		version semver.Version
+		entries []FragmentEntry
+		mg      MigrationGuide
+	}{
+		{
+			name:    "no entries, weight 1",
+			version: semver.MustParse("999.999.999"),
+			mg: MigrationGuide{
+				Version: "v999.999.999",
+				Weight:  1,
+			},
+		},
+		{
+			name:    "no entries, weight 2",
+			version: semver.MustParse("999.999.998"),
+			mg: MigrationGuide{
+				Version: "v999.999.998",
+				Weight:  2,
+			},
+		},
+		{
+			name:    "no entries, weight 998_997_997",
+			version: semver.MustParse("1.2.3"),
+			mg: MigrationGuide{
+				Version: "v1.2.3",
+				Weight:  998_997_997,
+			},
+		},
+		{
+			name:    "no entries, weight 2",
+			version: semver.MustParse("3.2.1"),
+			mg: MigrationGuide{
+				Version: "v3.2.1",
+				Weight:  996_997_999,
+			},
+		},
+		{
+			name:    "some migrations",
+			version: semver.MustParse("999.999.999"),
+			entries: []FragmentEntry{
+				{
+					Description:     "Changelog entry description 0",
+					Kind:            Addition,
+					Breaking:        false,
+					PullRequestLink: "[#999999](https://example.com/test/changelog/pulls/999999)",
+					Migration: &EntryMigration{
+						Header: "Migration header 0",
+						Body:   "Migration body 0",
+					},
+				},
+				{
+					Description: "Changelog entry description 1",
+					Kind:        Change,
+					Breaking:    true,
+					Migration: &EntryMigration{
+						Header: "Migration header 1",
+						Body:   "Migration body 1",
+					},
+				},
+				{
+					Description: "Changelog entry description 2",
+					Kind:        Removal,
+					Breaking:    true,
+					Migration: &EntryMigration{
+						Header: "Migration header 2",
+						Body:   "Migration body 2",
+					},
+				},
+				{
+					Description: "Changelog entry description 0",
+					Kind:        Deprecation,
+					Breaking:    false,
+				},
+				{
+					Description: "Changelog entry description 0",
+					Kind:        Bugfix,
+					Breaking:    false,
+				},
+			},
+			mg: MigrationGuide{
+				Version: "v999.999.999",
+				Weight:  1,
+				Migrations: []Migration{
+					{
+						Header:          "Migration header 0",
+						Body:            "Migration body 0",
+						PullRequestLink: "[#999999](https://example.com/test/changelog/pulls/999999)",
+					},
+					{
+						Header: "Migration header 1",
+						Body:   "Migration body 1",
+					},
+					{
+						Header: "Migration header 2",
+						Body:   "Migration body 2",
+					},
+				},
+			},
+		},
+	}
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			mg := MigrationGuideFromEntries(tc.version, tc.entries)
+			assert.Equal(t, tc.mg, mg)
+		})
+	}
+}
diff --git a/hack/generate/changelog/util/testdata/ignore/00-template.yaml b/hack/generate/changelog/util/testdata/ignore/00-template.yaml
new file mode 100644
index 00000000000..44f68b5ba65
--- /dev/null
+++ b/hack/generate/changelog/util/testdata/ignore/00-template.yaml
@@ -0,0 +1,36 @@
+# entries is a list of entries to include in
+# release notes and/or the migration guide
+entries:
+  - description: >
+      Description is the line that shows up in the CHANGELOG. This
+      should be formatted as markdown and be on a single line. Using
+      the YAML string '>' operator means you can write your entry
+      multiple lines and it will still be parsed as a single line.
+
+    # kind is one of:
+    # - addition
+    # - change
+    # - deprecation
+    # - removal
+    # - bugfix
+    kind: ""
+
+    # Is this a breaking change?
+    breaking: false
+
+    # NOTE: ONLY USE `pull_request_override` WHEN ADDING THIS
+    # FILE FOR A PREVIOUSLY MERGED PULL_REQUEST!
+    #
+    # The generator auto-detects the PR number from the commit
+    # message in which this file was originally added.
+    #
+    # What is the pull request number (without the "#")?
+    # pull_request_override: 0
+
+
+    # Migration can be defined to automatically add a section to
+    # the migration guide. This is required for breaking changes.
+    migration:
+      header: Header text for the migration section
+      body: >
+        Body of the migration section.
diff --git a/hack/generate/changelog/util/testdata/ignore/more-fragments/ignored.yaml b/hack/generate/changelog/util/testdata/ignore/more-fragments/ignored.yaml
new file mode 100644
index 00000000000..ec264e46281
--- /dev/null
+++ b/hack/generate/changelog/util/testdata/ignore/more-fragments/ignored.yaml
@@ -0,0 +1,19 @@
+entries:
+  - addition: Addition description
+    kind: addition
+    breaking: false
+  - description: Change description
+    kind: change
+    breaking: false
+  - description: Removal description
+    kind: removal
+    breaking: true
+    migration:
+      header: Header for removal migration
+      body: Body for removal migration
+  - description: Deprecation description
+    kind: deprecation
+    breaking: false
+  - description: Bugfix description
+    kind: bugfix
+    breaking: false
\ No newline at end of file
diff --git a/hack/generate/changelog/util/testdata/ignore/non-yaml.txt b/hack/generate/changelog/util/testdata/ignore/non-yaml.txt
new file mode 100644
index 00000000000..e69de29bb2d
diff --git a/hack/generate/changelog/util/testdata/invalid_entry/fragment1.yaml b/hack/generate/changelog/util/testdata/invalid_entry/fragment1.yaml
new file mode 100644
index 00000000000..4fe900e556a
--- /dev/null
+++ b/hack/generate/changelog/util/testdata/invalid_entry/fragment1.yaml
@@ -0,0 +1,4 @@
+entries:
+  - description: Addition description 0
+    kind: addition
+    breaking: true
\ No newline at end of file
diff --git a/hack/generate/changelog/util/testdata/invalid_yaml/fragment1.yaml b/hack/generate/changelog/util/testdata/invalid_yaml/fragment1.yaml
new file mode 100644
index 00000000000..20d2807958b
--- /dev/null
+++ b/hack/generate/changelog/util/testdata/invalid_yaml/fragment1.yaml
@@ -0,0 +1,18 @@
+- description: Addition description 0
+  kind: addition
+  breaking: false
+- description: Change description 0
+  kind: change
+  breaking: false
+- description: Removal description 0
+  kind: removal
+  breaking: true
+  migration:
+    header: Header for removal migration 0
+    body: Body for removal migration 0
+- description: Deprecation description 0
+  kind: deprecation
+  breaking: false
+- description: Bugfix description 0
+  kind: bugfix
+  breaking: false
\ No newline at end of file
diff --git a/hack/generate/changelog/util/testdata/valid/fragment1.yaml b/hack/generate/changelog/util/testdata/valid/fragment1.yaml
new file mode 100644
index 00000000000..4c8d7428153
--- /dev/null
+++ b/hack/generate/changelog/util/testdata/valid/fragment1.yaml
@@ -0,0 +1,19 @@
+entries:
+  - description: Addition description 0
+    kind: addition
+    breaking: false
+  - description: Change description 0
+    kind: change
+    breaking: false
+  - description: Removal description 0
+    kind: removal
+    breaking: true
+    migration:
+      header: Header for removal migration 0
+      body: Body for removal migration 0
+  - description: Deprecation description 0
+    kind: deprecation
+    breaking: false
+  - description: Bugfix description 0
+    kind: bugfix
+    breaking: false
\ No newline at end of file
diff --git a/hack/generate/changelog/util/testdata/valid/fragment2.yaml b/hack/generate/changelog/util/testdata/valid/fragment2.yaml
new file mode 100644
index 00000000000..00e1313a818
--- /dev/null
+++ b/hack/generate/changelog/util/testdata/valid/fragment2.yaml
@@ -0,0 +1,24 @@
+entries:
+  - description: Addition description 1
+    kind: addition
+    breaking: false
+    pull_request_override: 999999
+  - description: Change description 1
+    kind: change
+    breaking: false
+    pull_request_override: 999999
+  - description: Removal description 1
+    kind: removal
+    breaking: true
+    pull_request_override: 999999
+    migration:
+      header: Header for removal migration 1
+      body: Body for removal migration 1
+  - description: Deprecation description 1
+    kind: deprecation
+    breaking: false
+    pull_request_override: 999999
+  - description: Bugfix description 1
+    kind: bugfix
+    breaking: false
+    pull_request_override: 999999
diff --git a/hack/generate/gen-cli-doc.go b/hack/generate/cli-doc/gen-cli-doc.go
similarity index 100%
rename from hack/generate/gen-cli-doc.go
rename to hack/generate/cli-doc/gen-cli-doc.go
diff --git a/hack/generate/cli-doc/gen-cli-doc.sh b/hack/generate/cli-doc/gen-cli-doc.sh
new file mode 100755
index 00000000000..5f789624694
--- /dev/null
+++ b/hack/generate/cli-doc/gen-cli-doc.sh
@@ -0,0 +1,3 @@
+#!/bin/bash
+
+go run ./hack/generate/cli-doc/gen-cli-doc.go
diff --git a/hack/generate/gen-cli-doc.sh b/hack/generate/gen-cli-doc.sh
deleted file mode 100755
index 5b716f55981..00000000000
--- a/hack/generate/gen-cli-doc.sh
+++ /dev/null
@@ -1,3 +0,0 @@
-#!/bin/bash
-
-go run ./hack/generate/gen-cli-doc.go
diff --git a/hack/generate/gen-test-framework.sh b/hack/generate/test-framework/gen-test-framework.sh
similarity index 100%
rename from hack/generate/gen-test-framework.sh
rename to hack/generate/test-framework/gen-test-framework.sh
diff --git a/hack/tests/sanity-check.sh b/hack/tests/sanity-check.sh
index 63a2ab14fdc..b708c282936 100755
--- a/hack/tests/sanity-check.sh
+++ b/hack/tests/sanity-check.sh
@@ -8,8 +8,9 @@ go fmt ./...
 ./hack/check-license.sh
 ./hack/check-error-log-msg-format.sh
 ./hack/check-doc-diffs.sh
-./hack/generate/gen-cli-doc.sh
-./hack/generate/gen-test-framework.sh
+./hack/generate/cli-doc/gen-cli-doc.sh
+./hack/generate/test-framework/gen-test-framework.sh
+go run ./hack/generate/changelog/gen-changelog.go -validate-only
 
 # Make sure repo is still in a clean state.
 git diff --exit-code
diff --git a/website/content/en/docs/contribution-guidelines/release.md b/website/content/en/docs/contribution-guidelines/release.md
index 20f183f9905..631768683ed 100644
--- a/website/content/en/docs/contribution-guidelines/release.md
+++ b/website/content/en/docs/contribution-guidelines/release.md
@@ -5,7 +5,7 @@ weight: 30
 
 Making an Operator SDK release involves:
 
-- Updating `CHANGELOG.md`.
+- Updating `CHANGELOG.md` and migration guide.
 - Tagging and signing a git commit and pushing the tag to GitHub.
 - Building a release binary and signing the binary
 - Creating a release by uploading binary, signature, and `CHANGELOG.md` updates for the release to GitHub.
@@ -196,7 +196,7 @@ $ git push origin release-v1.3.1
 
 Create a PR from `release-v1.3.1` to `v1.3.x`. Once CI passes and your PR is merged, continue to step 1.
 
-### 1. Create a PR for release version and CHANGELOG.md updates
+### 1. Create a PR for release version, CHANGELOG.md, and migration guide updates
 
 Once all PR's needed for a release have been merged, branch from `master`:
 
@@ -218,14 +218,22 @@ Create a new branch to push release commits:
 $ git checkout -b release-v1.3.0
 ```
 
+Run the CHANGELOG and migration guide generator:
+
+```sh
+$ GEN_CHANGELOG_TAG=v1.3.0 make gen-changelog
+```
+
 Commit the following changes:
 
 - `version/version.go`: update `Version` to `v1.3.0`.
 - `internal/scaffold/go_mod.go`, change the `require` line version for `github.com/operator-framework/operator-sdk` from `master` to `v1.3.0`.
 - `internal/scaffold/helm/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
 - `internal/scaffold/ansible/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
-- `CHANGELOG.md`: update the `## Unreleased` header to `## v1.3.0`.
 - `doc/user/install-operator-sdk.md`: update the linux and macOS URLs to point to the new release URLs.
+- `CHANGELOG.md`: commit changes (updated by changelog generation).
+- `website/content/en/docs/migration/v1.3.0.md`: commit changes (created by changelog generation).
+- `changelog/fragments/*`: commit deleted fragment files (deleted by changelog generation).
 
 _(Non-patch releases only)_ Lock down the master branch to prevent further commits between this and step 4. See [this section](#locking-down-branches) for steps to do so.
 
@@ -257,7 +265,7 @@ Once this tag passes CI, go to step 3. For more info on tagging, see the [releas
 
 **Note:** If CI fails for some reason, you will have to revert the tagged commit, re-commit, and make a new PR.
 
-### 3. Create a PR for post-release version and CHANGELOG.md updates
+### 3. Create a PR for post-release version updates
 
 Check out a new branch from master (or use your `release-v1.3.0` branch) and commit the following changes:
 
@@ -265,21 +273,6 @@ Check out a new branch from master (or use your `release-v1.3.0` branch) and com
 - `internal/scaffold/go_mod.go`, change the `require` line version for `github.com/operator-framework/operator-sdk` from `v1.3.0` to `master`.
 - `internal/scaffold/helm/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
 - `internal/scaffold/ansible/go_mod.go`: same as for `internal/scaffold/go_mod.go`.
-- `CHANGELOG.md`: add the following as a new set of headers above `## v1.3.0`:
-
-    ```markdown
-    ## Unreleased
-
-    ### Added
-
-    ### Changed
-
-    ### Deprecated
-
-    ### Removed
-
-    ### Bug Fixes
-    ```
 
 Create a new PR for this branch, targetting the `master` branch. Once this PR passes CI and is merged, `master` can be unfrozen.