diff --git a/tools/wpdev/src/commands/bundle.ts b/tools/wpdev/src/commands/bundle.ts
index dbfcfb29..d3a41686 100644
--- a/tools/wpdev/src/commands/bundle.ts
+++ b/tools/wpdev/src/commands/bundle.ts
@@ -234,11 +234,12 @@ export default class Bundle extends WithProjects<typeof Bundle> {
 							return task.skip();
 						}
 
-						const { readmeTxtFile } = bundle.tasks.updateChangelog;
+						const { readmeTxtFile, ...config } = bundle.tasks.updateChangelog;
 
 						return updateChangelog({
 							changesetJsonFile: this.flags['changeset-json'],
 							readmeTxtFile: path.join(project.dir, readmeTxtFile),
+							...config,
 							packageName: project.packageJson.name,
 							version,
 						});
diff --git a/tools/wpdev/src/utils/changelog.ts b/tools/wpdev/src/utils/changelog.ts
index 6a0cee59..cd819bde 100644
--- a/tools/wpdev/src/utils/changelog.ts
+++ b/tools/wpdev/src/utils/changelog.ts
@@ -35,10 +35,35 @@ type UpdateChangelogConfig = UpdateChangelogOptions & {
 
 export function updateChangelog({
 	changesetJsonFile,
+	defaultChange,
 	readmeTxtFile,
+	prevChangesPattern,
 	packageName,
 	version,
 }: UpdateChangelogConfig) {
+	let readmeTxt = fs.readFileSync(readmeTxtFile, 'utf8');
+
+	const versionStr = `= ${version} =`;
+
+	const prevChangesRegex =
+		prevChangesPattern.pattern instanceof RegExp
+			? prevChangesPattern.pattern
+			: new RegExp(
+					prevChangesPattern.pattern,
+					'flags' in prevChangesPattern ? prevChangesPattern.flags : 's',
+			  );
+
+	const prevChanges = readmeTxt.match(prevChangesRegex);
+
+	/**
+	 * The pattern must have a capturing group for actual changes.
+	 *
+	 * If the version is already in the changelog, skip.
+	 */
+	if (!prevChanges?.[1] || prevChanges[0].includes(versionStr)) {
+		return;
+	}
+
 	const data = readChangesetJson(changesetJsonFile);
 
 	const changesetsMap = new Map(
@@ -65,20 +90,19 @@ export function updateChangelog({
 		}
 	}
 
-	let readmeTxt = fs.readFileSync(readmeTxtFile, 'utf8');
-
-	const versionStr = `= ${version} =`;
-
 	if (!changes.length) {
-		changes.push('- Maintenance release.');
+		changes.push(`- ${defaultChange}`);
 	}
 
 	const changesStr = changes.join('\n');
 
-	readmeTxt = readmeTxt.replace(
-		/== Changelog ==\n.*?\[See full changelog\]/s,
-		`== Changelog ==\n\n${versionStr}\n${changesStr}\n\n[See full changelog]`,
+	// Replace the captured group with the new changes
+	const updatedChanges = prevChanges[0].replace(
+		prevChanges[1],
+		`${versionStr}\n${changesStr}`,
 	);
 
+	readmeTxt = readmeTxt.replace(prevChangesRegex, updatedChanges);
+
 	fs.writeFileSync(readmeTxtFile, readmeTxt);
 }
diff --git a/tools/wpdev/src/utils/schema.ts b/tools/wpdev/src/utils/schema.ts
index 23a553e8..01c42f18 100644
--- a/tools/wpdev/src/utils/schema.ts
+++ b/tools/wpdev/src/utils/schema.ts
@@ -109,8 +109,29 @@ const updateRequirementsData = z.object({
 	target: targetFilesSchema.describe('The target files.'),
 });
 
+const pattern = z.union([
+	z.object({
+		pattern: z.string().describe('The text pattern to match.'),
+		flags: z.string().optional().describe('The regex flags.'),
+	}),
+	z.object({
+		pattern: z.instanceof(RegExp).describe('The regex pattern to match.'),
+	}),
+]);
+
 const updateChangelogData = z.object({
 	readmeTxtFile: z.string().optional().default('src/readme.txt'),
+	defaultChange: z.string().optional().default('Maintenance release.'),
+	prevChangesPattern: pattern
+		.optional()
+		.default({
+			pattern:
+				'== Changelog ==[\\n]{1,2}(.*?)[\\n]{1,2}\\[See full changelog\\]',
+			flags: 's',
+		})
+		.describe(
+			'The regex to match the previous changelog. The pattern must have a capturing group for actual changes.',
+		),
 });
 
 const updateVersionData = z.array(
@@ -140,17 +161,7 @@ const updateVersionData = z.array(
 			.object({
 				type: z.literal('general'),
 				textPatterns: z
-					.array(
-						z.union([
-							z.object({
-								pattern: z.string(),
-								flags: z.string().optional(),
-							}),
-							z.object({
-								pattern: z.instanceof(RegExp),
-							}),
-						]),
-					)
+					.array(pattern)
 					.describe('The text patterns to match. Regex can also be used.'),
 			})
 			.merge(targetFilesSchema),