diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
index 2eb6414caed91..d6a3689597bac 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
@@ -266,7 +266,6 @@ export function buildModelPickerItems(
 		}
 
 		// Render promoted section: available first, then sorted alphabetically by name
-		let hasShownActionLink = false;
 		if (promotedItems.length > 0) {
 			promotedItems.sort((a, b) => {
 				const aAvail = a.kind === 'available' ? 0 : 1;
@@ -283,11 +282,7 @@ export function buildModelPickerItems(
 				if (item.kind === 'available') {
 					items.push(createModelItem(createModelAction(item.model, selectedModelId, onSelect), item.model));
 				} else {
-					const showActionLink = item.reason === 'upgrade' ? !hasShownActionLink : true;
-					if (showActionLink && item.reason === 'upgrade') {
-						hasShownActionLink = true;
-					}
-					items.push(createUnavailableModelItem(item.id, item.entry, item.reason, manageSettingsUrl, updateStateType, undefined, showActionLink));
+					items.push(createUnavailableModelItem(item.id, item.entry, item.reason, manageSettingsUrl, updateStateType));
 				}
 			}
 		}
@@ -336,7 +331,7 @@ export function buildModelPickerItems(
 			for (const model of otherModels) {
 				const entry = controlModels[model.metadata.id] ?? controlModels[model.identifier];
 				if (entry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
-					items.push(createUnavailableModelItem(model.metadata.id, entry, 'update', manageSettingsUrl, updateStateType, ModelPickerSection.Other, true));
+					items.push(createUnavailableModelItem(model.metadata.id, entry, 'update', manageSettingsUrl, updateStateType, ModelPickerSection.Other));
 				} else {
 					items.push(createModelItem(createModelAction(model, selectedModelId, onSelect, ModelPickerSection.Other), model));
 				}
@@ -398,14 +393,11 @@ function createUnavailableModelItem(
 	manageSettingsUrl: string | undefined,
 	updateStateType: StateType,
 	section?: string,
-	showActionLink: boolean = true,
 ): IActionListItem<IActionWidgetDropdownAction> {
 	let description: string | MarkdownString | undefined;
 
 	if (reason === 'upgrade') {
-		description = showActionLink
-			? new MarkdownString(localize('chat.modelPicker.upgradeLink', "[Upgrade your plan](command:workbench.action.chat.upgradePlan \" \")"), { isTrusted: true })
-			: undefined;
+		description = new MarkdownString(localize('chat.modelPicker.upgradeLink', "[Upgrade your plan](command:workbench.action.chat.upgradePlan \" \")"), { isTrusted: true });
 	} else if (reason === 'update') {
 		description = localize('chat.modelPicker.updateDescription', "Update VS Code");
 	} else {
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
index b9d21246bba9c..d74122c7f6155 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
@@ -580,7 +580,7 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(unavailable.group?.icon?.id, Codicon.blank.id);
 	});
 
-	test('anonymous user sees upgrade description only on first unavailable model', () => {
+	test('anonymous user sees upgrade description on each unavailable model', () => {
 		const auto = createAutoModel();
 		const items = callBuild([auto], {
 			recentModelIds: ['model-a', 'model-b'],
@@ -596,10 +596,11 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(disabledItems.length, 2);
 		assert.ok(disabledItems[0].description instanceof MarkdownString);
 		assert.ok(disabledItems[0].description.value.includes('Upgrade'));
-		assert.strictEqual(disabledItems[1].description, undefined);
+		assert.ok(disabledItems[1].description instanceof MarkdownString);
+		assert.ok(disabledItems[1].description.value.includes('Upgrade'));
 	});
 
-	test('free user sees upgrade description only on first unavailable model', () => {
+	test('free user sees upgrade description on each unavailable model', () => {
 		const auto = createAutoModel();
 		const items = callBuild([auto], {
 			recentModelIds: ['model-a', 'model-b'],
@@ -614,7 +615,8 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(disabledItems.length, 2);
 		assert.ok(disabledItems[0].description instanceof MarkdownString);
 		assert.ok(disabledItems[0].description.value.includes('Upgrade'));
-		assert.strictEqual(disabledItems[1].description, undefined);
+		assert.ok(disabledItems[1].description instanceof MarkdownString);
+		assert.ok(disabledItems[1].description.value.includes('Upgrade'));
 	});
 
 	test('anonymous user model selection triggers onSelect normally', () => {