diff --git a/GNUmakefile b/GNUmakefile
index b221f6490..12fe7527c 100644
--- a/GNUmakefile
+++ b/GNUmakefile
@@ -409,3 +409,8 @@ missing: ## Check for packages not being tested
 ec2info: ## Generate AWS EC2 CPU specification table
 	@echo "==> Generating AWS EC2 specifications ..."
 	@go run -modfile tools/go.mod tools/ec2info/main.go
+
+.PHONY: cl
+cl: ## Create a new Changelog entry
+	@go run -modfile tools/go.mod tools/cl-entry/main.go
+
diff --git a/contributing/CHANGELOG.md b/contributing/CHANGELOG.md
index c7816d6d5..27e346656 100644
--- a/contributing/CHANGELOG.md
+++ b/contributing/CHANGELOG.md
@@ -18,6 +18,12 @@ Use the PR number as the file name. Enterprise private changes should have an en
 
 The `.txt` files have a markdown-like syntax, with a tag signifying the entry type.
 
+Use the `tools/cl-entry` command to help generate a changelog entry file.
+
+```shell
+make cl
+```
+
 Below are some examples of how to generate a CHANGELOG entry with your pull request.
 
 ### Improvement
diff --git a/tools/cl-entry/main.go b/tools/cl-entry/main.go
new file mode 100644
index 000000000..477fd6228
--- /dev/null
+++ b/tools/cl-entry/main.go
@@ -0,0 +1,128 @@
+package main
+
+import (
+	"bufio"
+	"errors"
+	"fmt"
+	"os"
+	"path/filepath"
+	"regexp"
+	"strconv"
+	"strings"
+)
+
+const (
+	pr = `Must have a Pull Request already open.
+  Enter PR # => `
+
+	kind = `Choose type, one of
+    1. bug
+    2. improvement
+    3. security
+    4. breaking-change
+    5. note
+    6. deprecation
+  Enter Kind => `
+
+	note = `Write a note, for example
+	build: Added make target for creating changelog entries
+  Enter Note => `
+)
+
+var noteRe = regexp.MustCompile(`[a-z0-9/\s]+: .+`)
+
+func main() {
+	pr, err := ask(pr)
+	check(err)
+
+	n, err := ask(kind)
+	check(err)
+
+	label, err := label(n)
+	check(err)
+
+	body, err := askStr(note)
+	check(err)
+
+	msg, err := cleanup(body)
+	check(err)
+
+	file, err := write(pr, label, msg)
+	check(err)
+
+	fmt.Println("Created", file)
+}
+
+func write(pr int, label, msg string) (string, error) {
+	filename := filepath.Join(".changelog", fmt.Sprintf("%d.txt", pr))
+	sb := new(strings.Builder)
+	sb.WriteString("```release-note:")
+	sb.WriteString(label)
+	sb.WriteString("\n")
+	sb.WriteString(msg)
+	sb.WriteString("\n")
+	sb.WriteString("```\n")
+	s := sb.String()
+	if err := os.WriteFile(filename, []byte(s), 0o644); err != nil {
+		return "", err
+	}
+	return filename, nil
+}
+
+func cleanup(note string) (string, error) {
+	note = strings.TrimSpace(note)
+	note = strings.TrimSuffix(note, ".")
+	if !noteRe.MatchString(note) {
+		return "", errors.New("note does not comply with format")
+	}
+	return note, nil
+}
+
+func label(n int) (string, error) {
+	var label string
+	switch n {
+	case 1:
+		label = "bug"
+	case 2:
+		label = "improvement"
+	case 3:
+		label = "security"
+	case 4:
+		label = "breaking-change"
+	case 5:
+		label = "note"
+	case 6:
+		label = "deprecation"
+	default:
+		return "", errors.New("not a valid type, must be 1-6")
+	}
+	return label, nil
+}
+
+func ask(q string) (int, error) {
+	r := bufio.NewReader(os.Stdin)
+	fmt.Print(q)
+	line, err := r.ReadString('\n')
+	if err != nil {
+		return 0, err
+	}
+	i, err := strconv.Atoi(strings.TrimSpace(line))
+	if err != nil {
+		return 0, err
+	}
+	return i, nil
+}
+
+func askStr(q string) (string, error) {
+	r := bufio.NewReader(os.Stdin)
+	fmt.Print(q)
+	line, err := r.ReadString('\n')
+	return strings.TrimSpace(line), err
+}
+
+func check(err error) {
+	if err != nil {
+		fmt.Fprintf(os.Stderr, "failure: %v\n", err)
+		os.Exit(1)
+	}
+}
diff --git a/tools/go.mod b/tools/go.mod
index 4e570d979..a36f7ad90 100644
--- a/tools/go.mod
+++ b/tools/go.mod
@@ -1,11 +1,11 @@
 module github.com/hashicorp/nomad/tools
 
-go 1.18
+go 1.19
 
 require (
 	github.com/aws/aws-sdk-go v1.37.26
 	github.com/hashicorp/go-set v0.1.6
-	github.com/shoenig/test v0.4.0
+	github.com/shoenig/test v0.4.4
 )
 
 require (
diff --git a/tools/go.sum b/tools/go.sum
index 5433d3e56..271d35160 100644
--- a/tools/go.sum
+++ b/tools/go.sum
@@ -13,8 +13,8 @@ github.com/jmespath/go-jmespath/internal/testify v1.5.1/go.mod h1:L3OGu8Wl2/fWfC
 github.com/pkg/errors v0.9.1/go.mod h1:bwawxfHBFNV+L2hUp1rHADufV3IMtnDRdf1r5NINEl0=
 github.com/pmezard/go-difflib v1.0.0 h1:4DBwDE0NGyQoBHbLQYPwSUPoCMWR5BEzIk/f1lZbAQM=
 github.com/pmezard/go-difflib v1.0.0/go.mod h1:iKH77koFhYxTK1pcRnkKkqfTogsbg7gZNVY4sRDYZ/4=
-github.com/shoenig/test v0.4.0 h1:3X4xG/Chx7mzi0h71Sm6Vo38q0EYaQIBZpYFRcA1HVM=
-github.com/shoenig/test v0.4.0/go.mod h1:xYtyGBC5Q3kzCNyJg/SjgNpfAa2kvmgA0i5+lQso8x0=
+github.com/shoenig/test v0.4.4 h1:juucmjQTPYUfO2+rID1wfQqsreSlk+2I8K/bQFsUZ9c=
+github.com/shoenig/test v0.4.4/go.mod h1:xYtyGBC5Q3kzCNyJg/SjgNpfAa2kvmgA0i5+lQso8x0=
 github.com/stretchr/objx v0.1.0/go.mod h1:HFkY916IF+rwdDfMAkV7OtwuqBVzrE8GR6GFx+wExME=
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20200622213623-75b288015ac9/go.mod h1:LzIPMQfyMNhhGPhUkYOs5KpL4U8rLKemX1yGLhDgUto=