diff --git a/packages/coding-agent/src/modes/interactive/interactive-mode.ts b/packages/coding-agent/src/modes/interactive/interactive-mode.ts
index 77135ee28..b105eb1f1 100644
--- a/packages/coding-agent/src/modes/interactive/interactive-mode.ts
+++ b/packages/coding-agent/src/modes/interactive/interactive-mode.ts
@@ -104,11 +104,11 @@ import type { TruncationResult } from "../../core/tools/truncate.ts";
 import { hasTrustRequiringProjectResources, ProjectTrustStore } from "../../core/trust-manager.ts";
 import { getUsageCostBreakdown } from "../../core/usage-totals.ts";
 import {
+	formatStartupChangelogPreviewLines,
 	getChangelogPath,
-	getNewEntries,
-	getStartupChangelogPreviewLines,
 	normalizeChangelogLinks,
 	parseChangelog,
+	selectStartupChangelogEntries,
 } from "../../utils/changelog.ts";
 import { copyToClipboard, readClipboardText } from "../../utils/clipboard.ts";
 import { extensionForImageMimeType, readClipboardImage } from "../../utils/clipboard-image.ts";
@@ -1188,7 +1188,11 @@ export class InteractiveMode {
 	}
 
 	private getStartupWhatsNewLines(): string[] {
-		const previewLines = getStartupChangelogPreviewLines(getChangelogPath());
+		if (!this.changelogMarkdown) {
+			return [];
+		}
+
+		const previewLines = formatStartupChangelogPreviewLines(this.changelogMarkdown);
 		if (previewLines.length === 0) {
 			return [];
 		}
@@ -1215,22 +1219,16 @@ export class InteractiveMode {
 		const lastVersion = this.settingsManager.getLastChangelogVersion();
 		const changelogPath = getChangelogPath();
 		const entries = parseChangelog(changelogPath);
+		const selection = selectStartupChangelogEntries(entries, lastVersion);
 
-		if (!lastVersion) {
-			// Fresh install - record the version, send telemetry, don't show changelog
-			this.settingsManager.setLastChangelogVersion(VERSION);
+		if (selection.checkpointVersion && selection.checkpointVersion !== lastVersion) {
+			this.settingsManager.setLastChangelogVersion(selection.checkpointVersion);
 			this.reportInstallTelemetry(VERSION);
-			return undefined;
 		}
 
-		const newEntries = getNewEntries(entries, lastVersion);
-		if (newEntries.length > 0) {
-			this.settingsManager.setLastChangelogVersion(VERSION);
-			this.reportInstallTelemetry(VERSION);
-			return newEntries.map((e) => normalizeChangelogLinks(e.content, e)).join("\n\n");
-		}
-
-		return undefined;
+		return selection.entries.length > 0
+			? selection.entries.map((entry) => normalizeChangelogLinks(entry.content, entry)).join("\n\n")
+			: undefined;
 	}
 
 	private reportInstallTelemetry(version: string): void {
diff --git a/packages/coding-agent/src/utils/changelog.ts b/packages/coding-agent/src/utils/changelog.ts
index c4bb825d0..2bb87f800 100644
--- a/packages/coding-agent/src/utils/changelog.ts
+++ b/packages/coding-agent/src/utils/changelog.ts
@@ -26,10 +26,44 @@ export interface StartupChangelogPreviewOptions {
 	maxWidth?: number;
 }
 
+export interface StartupChangelogSelection {
+	checkpointVersion?: string;
+	entries: ChangelogEntry[];
+}
+
 function entryVersion(entry: ChangelogEntry): string {
 	return `${entry.major}.${entry.minor}.${entry.patch}`;
 }
 
+/**
+ * Select changelog entries that appear before the last acknowledged entry.
+ *
+ * Startup tracking follows document order instead of semver so repositories
+ * can reset their package version without replaying inherited release notes.
+ * Unknown markers are treated as a migration baseline rather than as a reason
+ * to display the complete changelog.
+ */
+export function selectStartupChangelogEntries(
+	entries: ChangelogEntry[],
+	lastVersion: string | undefined,
+): StartupChangelogSelection {
+	const checkpointVersion = entries[0] ? entryVersion(entries[0]) : undefined;
+	if (!checkpointVersion || !lastVersion) {
+		return { checkpointVersion, entries: [] };
+	}
+
+	const normalizedLastVersion = lastVersion.trim().replace(/^v/i, "");
+	const lastSeenIndex = entries.findIndex((entry) => entryVersion(entry) === normalizedLastVersion);
+	if (lastSeenIndex <= 0) {
+		return { checkpointVersion, entries: [] };
+	}
+
+	return {
+		checkpointVersion,
+		entries: entries.slice(0, lastSeenIndex),
+	};
+}
+
 function normalizeTag(version: string | ChangelogEntry): string {
 	const versionString = typeof version === "string" ? version : entryVersion(version);
 	return versionString.startsWith("v") ? versionString : `v${versionString}`;
diff --git a/packages/coding-agent/test/changelog.test.ts b/packages/coding-agent/test/changelog.test.ts
index bad2bfd5d..34387c593 100644
--- a/packages/coding-agent/test/changelog.test.ts
+++ b/packages/coding-agent/test/changelog.test.ts
@@ -3,6 +3,7 @@ import {
 	type ChangelogEntry,
 	formatStartupChangelogPreviewLines,
 	normalizeChangelogLinks,
+	selectStartupChangelogEntries,
 } from "../src/utils/changelog.ts";
 
 const entry: ChangelogEntry = {
@@ -80,3 +81,40 @@ describe("formatStartupChangelogPreviewLines", () => {
 		]);
 	});
 });
+
+describe("selectStartupChangelogEntries", () => {
+	const changelogEntries: ChangelogEntry[] = [
+		{ major: 0, minor: 3, patch: 0, content: "## [0.3.0]\n\n- Current Diffex release" },
+		{ major: 0, minor: 84, patch: 0, content: "## [0.84.0]\n\n- Inherited release" },
+		{ major: 0, minor: 83, patch: 0, content: "## [0.83.0]\n\n- Older inherited release" },
+	];
+
+	test("uses changelog order when package versions have been reset", () => {
+		expect(selectStartupChangelogEntries(changelogEntries, "0.84.0")).toEqual({
+			checkpointVersion: "0.3.0",
+			entries: [changelogEntries[0]],
+		});
+	});
+
+	test("acknowledges fresh installs and legacy markers without replaying history", () => {
+		expect(selectStartupChangelogEntries(changelogEntries, undefined)).toEqual({
+			checkpointVersion: "0.3.0",
+			entries: [],
+		});
+		expect(selectStartupChangelogEntries(changelogEntries, "0.2.0")).toEqual({
+			checkpointVersion: "0.3.0",
+			entries: [],
+		});
+	});
+
+	test("returns no startup entries after the current checkpoint is seen", () => {
+		expect(selectStartupChangelogEntries(changelogEntries, "v0.3.0")).toEqual({
+			checkpointVersion: "0.3.0",
+			entries: [],
+		});
+		expect(selectStartupChangelogEntries([], "0.3.0")).toEqual({
+			checkpointVersion: undefined,
+			entries: [],
+		});
+	});
+});