diff --git a/apps/cli/commands/pull-reprint.ts b/apps/cli/commands/pull-reprint.ts
index e5fd404cab..c083f6a50f 100644
--- a/apps/cli/commands/pull-reprint.ts
+++ b/apps/cli/commands/pull-reprint.ts
@@ -9,6 +9,7 @@ import crypto from 'crypto';
 import fs from 'fs';
 import os from 'os';
 import path from 'path';
+import { search } from '@inquirer/prompts';
 import { DEFAULT_PHP_VERSION } from '@studio/common/constants';
 import { SITE_EVENTS } from '@studio/common/lib/cli-events';
 import * as fsUtils from '@studio/common/lib/fs-utils';
@@ -123,13 +124,6 @@ export const registerCommand = ( yargs: StudioArgv ) => {
  */
 const PULLS_ROOT = path.join( os.homedir(), '.studio', 'pulls' );
 
-/**
- * Display a hint with this many WordPress.com sites when the user calls just
- * `studio pull-reprint` without the `--url`. Some accounts have hundreds of sites.
- * Let's only display the first few.
- */
-const DEFAULT_WPCOM_SITE_LIST_LIMIT = 15;
-
 const pullStageOrder = [
 	'initialized',
 	'essential-files-complete',
@@ -1041,20 +1035,70 @@ export function findMatchingWpComSite(
 	} );
 }
 
-export function formatWpComSitesList(
-	sites: WpComSiteInfo[],
-	limit = DEFAULT_WPCOM_SITE_LIST_LIMIT
-): string {
-	const visibleSites = sites.slice( 0, limit );
-	const lines = visibleSites.map(
-		( site, index ) => `${ index + 1 }. ${ site.name } - ${ site.url }`
-	);
+/**
+ * Interactive searchable picker for WordPress.com sites.  Shared as a
+ * module-level export so tests can spy on / mock it without driving
+ * `@inquirer/prompts` directly.
+ */
+export async function pickWpComSite(
+	sites: WpComSiteInfo[]
+): Promise< WpComSiteInfo | undefined > {
+	const choices = sites.map( ( site ) => ( {
+		name: `${ site.name } ${ chalk.dim( site.url ) }`,
+		value: site.id,
+	} ) );
+
+	const abortController = new AbortController();
+	const handleEscKey = ( chunk: Buffer | string ) => {
+		const bytes = Buffer.isBuffer( chunk ) ? chunk : Buffer.from( chunk );
+		if ( bytes.length === 1 && bytes[ 0 ] === 0x1b ) {
+			abortController.abort();
+		}
+	};
 
-	if ( sites.length > visibleSites.length ) {
-		lines.push( `... and ${ sites.length - visibleSites.length } more.` );
+	if ( process.stdin.isTTY ) {
+		process.stdin.on( 'data', handleEscKey );
 	}
 
-	return lines.join( '\n' );
+	try {
+		const selectedId = await search(
+			{
+				message: __( 'Select a WordPress.com site to pull:' ),
+				source: ( term ) => {
+					if ( ! term ) {
+						return choices;
+					}
+					const lowerTerm = term.toLowerCase();
+					return choices.filter( ( choice ) => {
+						const site = sites.find( ( s ) => s.id === choice.value );
+						if ( ! site ) {
+							return false;
+						}
+						return (
+							site.name.toLowerCase().includes( lowerTerm ) ||
+							site.url.toLowerCase().includes( lowerTerm )
+						);
+					} );
+				},
+				pageSize: 12,
+			},
+			{ signal: abortController.signal }
+		);
+
+		return sites.find( ( site ) => site.id === selectedId );
+	} catch ( error ) {
+		if (
+			error instanceof Error &&
+			( error.name === 'AbortPromptError' || error.name === 'ExitPromptError' )
+		) {
+			return undefined;
+		}
+		throw error;
+	} finally {
+		if ( process.stdin.isTTY ) {
+			process.stdin.off( 'data', handleEscKey );
+		}
+	}
 }
 
 /**
@@ -1066,9 +1110,10 @@ export function formatWpComSitesList(
  *   2. `--url` alone — try a previously cached secret from an earlier
  *      run for this URL; fall back to rotating a fresh WP.com secret.
  *   3. No `--url` — if the user has exactly one connected WP.com
- *      site, pick it; otherwise list and abort.
+ *      site, pick it automatically; otherwise show an interactive
+ *      picker.
  */
-async function resolveSourceSite(
+export async function resolveSourceSite(
 	url?: string,
 	providedSecret?: string,
 	providedName?: string,
@@ -1139,18 +1184,24 @@ async function resolveSourceSite(
 		}
 
 		if ( sites.length > 1 ) {
-			console.log( __( 'Connected WordPress.com sites:' ) );
-			console.log( formatWpComSitesList( sites ) );
-			console.log( '' );
-			throw new LoggerError(
-				__( 'Multiple WordPress.com sites are available. Re-run with `--url <site-url>`.' )
-			);
+			const picked = await pickWpComSite( sites );
+			if ( ! picked ) {
+				throw new LoggerError( __( 'No WordPress.com site selected.' ) );
+			}
+			wpComSite = picked;
+			resolvedUrl = picked.url;
+		} else {
+			// If the user only has one connected WordPress.com site, pull it by default.
+			wpComSite = sites[ 0 ];
+			resolvedUrl = wpComSite.url;
+			console.log( `${ __( 'Using your only connected WordPress.com site:' ) } ${ resolvedUrl }` );
 		}
 
-		// If the user only has one connected WordPress.com site, pull it by default.
-		wpComSite = sites[ 0 ];
-		resolvedUrl = wpComSite.url;
-		console.log( `${ __( 'Using your only connected WordPress.com site:' ) } ${ resolvedUrl }` );
+		console.log(
+			__(
+				'Note: pull-reprint currently only works with WP Cloud-hosted WordPress.com sites (Personal plan and above).'
+			)
+		);
 		console.log( '' );
 	}
 
diff --git a/apps/cli/commands/tests/pull-reprint.test.ts b/apps/cli/commands/tests/pull-reprint.test.ts
index cbd3c76b9c..4e73d78f2b 100644
--- a/apps/cli/commands/tests/pull-reprint.test.ts
+++ b/apps/cli/commands/tests/pull-reprint.test.ts
@@ -1,20 +1,39 @@
 import fs from 'node:fs';
 import os from 'node:os';
 import path from 'node:path';
-import { afterEach, describe, expect, it, vi } from 'vitest';
+import { search } from '@inquirer/prompts';
+import { readAuthToken } from '@studio/common/lib/shared-config';
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest';
+import { getWpComSites, rotateReprintSecret } from 'cli/lib/api';
 import * as migrationClient from 'cli/lib/pull/migration-client';
 import { shouldRestartFilesSyncIndex } from 'cli/lib/pull/reprint-state';
 import {
 	applyDownloadedDatabase,
 	downloadSkippedFiles,
 	findMatchingWpComSite,
-	formatWpComSitesList,
 	getReprintApiUrlForSite,
+	pickWpComSite,
 	getPrivateDirNameForImportSession,
 	inferSiteNameFromUrl,
 	normalizeSiteUrl,
+	resolveSourceSite,
 } from '../pull-reprint';
 
+vi.mock( '@inquirer/prompts', () => ( {
+	search: vi.fn(),
+} ) );
+
+vi.mock( import( '@studio/common/lib/shared-config' ), async ( importOriginal ) => ( {
+	...( await importOriginal() ),
+	readAuthToken: vi.fn(),
+} ) );
+
+vi.mock( 'cli/lib/api', async () => ( {
+	...( await vi.importActual( 'cli/lib/api' ) ),
+	getWpComSites: vi.fn(),
+	rotateReprintSecret: vi.fn(),
+} ) );
+
 describe( 'CLI: studio pull-reprint helpers', () => {
 	it( 'normalizes URLs by stripping hashes and trailing slashes', () => {
 		expect( normalizeSiteUrl( 'https://example.com/foo//#section' ) ).toBe(
@@ -70,16 +89,25 @@ describe( 'CLI: studio pull-reprint helpers', () => {
 		} );
 	} );
 
-	it( 'formats the truncated WordPress.com site list with a remaining-count suffix', () => {
-		expect(
-			formatWpComSitesList(
-				[
-					{ id: 1, name: 'One', url: 'https://one.wordpress.com' },
-					{ id: 2, name: 'Two', url: 'https://two.wordpress.com' },
-				],
-				1
-			)
-		).toContain( '... and 1 more.' );
+	it( 'returns the WordPress.com site selected through the interactive picker', async () => {
+		const sites = [
+			{ id: 1, name: 'One', url: 'https://one.wordpress.com' },
+			{ id: 2, name: 'Two', url: 'https://two.wordpress.com' },
+		];
+		vi.mocked( search ).mockResolvedValueOnce( 2 );
+
+		const picked = await pickWpComSite( sites );
+
+		expect( picked ).toEqual( sites[ 1 ] );
+		expect( search ).toHaveBeenCalledOnce();
+	} );
+
+	it( 'returns undefined when the user cancels the picker', async () => {
+		const sites = [ { id: 1, name: 'One', url: 'https://one.wordpress.com' } ];
+		const abortError = Object.assign( new Error( 'aborted' ), { name: 'AbortPromptError' } );
+		vi.mocked( search ).mockRejectedValueOnce( abortError );
+
+		await expect( pickWpComSite( sites ) ).resolves.toBeUndefined();
 	} );
 
 	it( 'restarts files-sync indexing only when the saved state has no resumable cursor', () => {
@@ -177,6 +205,90 @@ describe( 'CLI: studio pull-reprint helpers', () => {
 	} );
 } );
 
+describe( 'CLI: studio pull-reprint resolveSourceSite', () => {
+	const mockToken = {
+		accessToken: 'mock-token',
+		id: 1,
+		expiresIn: 3600,
+		expirationTime: Date.now() + 3_600_000,
+		email: 'test@example.com',
+		displayName: 'Test User',
+	};
+
+	beforeEach( () => {
+		vi.mocked( readAuthToken ).mockResolvedValue( mockToken );
+		vi.mocked( rotateReprintSecret ).mockResolvedValue( 'rotated-secret' );
+	} );
+
+	afterEach( () => {
+		vi.mocked( search ).mockReset();
+		vi.mocked( getWpComSites ).mockReset();
+		vi.mocked( rotateReprintSecret ).mockReset();
+		vi.mocked( readAuthToken ).mockReset();
+	} );
+
+	it( 'invokes the interactive picker when no URL is provided and the user has multiple WP.com sites', async () => {
+		const sites = [
+			{ id: 1, name: 'One', url: 'https://one.wordpress.com' },
+			{ id: 2, name: 'Two', url: 'https://two.wordpress.com' },
+		];
+		vi.mocked( getWpComSites ).mockResolvedValueOnce( sites );
+		vi.mocked( search ).mockResolvedValueOnce( 2 );
+
+		const result = await resolveSourceSite();
+
+		expect( search ).toHaveBeenCalledOnce();
+		expect( getWpComSites ).toHaveBeenCalledWith( mockToken.accessToken );
+		expect( result?.url ).toBe( 'https://two.wordpress.com' );
+		expect( result?.wpComSite ).toEqual( sites[ 1 ] );
+		expect( rotateReprintSecret ).toHaveBeenCalledWith( 2, mockToken.accessToken );
+	} );
+
+	it( 'auto-picks the single connected WP.com site without prompting', async () => {
+		const sites = [ { id: 1, name: 'Solo', url: 'https://solo.wordpress.com' } ];
+		vi.mocked( getWpComSites ).mockResolvedValueOnce( sites );
+
+		const result = await resolveSourceSite();
+
+		expect( search ).not.toHaveBeenCalled();
+		expect( result?.url ).toBe( 'https://solo.wordpress.com' );
+	} );
+
+	it( 'does not invoke the picker when a URL is provided alongside a secret', async () => {
+		const result = await resolveSourceSite( 'https://example.com', 'trusted-secret' );
+
+		expect( search ).not.toHaveBeenCalled();
+		expect( getWpComSites ).not.toHaveBeenCalled();
+		expect( result ).toEqual( { url: 'https://example.com', secret: 'trusted-secret' } );
+	} );
+
+	it( 'does not invoke the picker when the user passes a URL that matches a WP.com site', async () => {
+		const sites = [
+			{ id: 1, name: 'One', url: 'https://one.wordpress.com' },
+			{ id: 2, name: 'Two', url: 'https://two.wordpress.com' },
+		];
+		vi.mocked( getWpComSites ).mockResolvedValueOnce( sites );
+
+		const result = await resolveSourceSite( 'https://two.wordpress.com' );
+
+		expect( search ).not.toHaveBeenCalled();
+		expect( result?.url ).toBe( 'https://two.wordpress.com' );
+		expect( result?.wpComSite ).toEqual( sites[ 1 ] );
+	} );
+
+	it( 'throws a helpful error when the user cancels the picker', async () => {
+		vi.mocked( getWpComSites ).mockResolvedValueOnce( [
+			{ id: 1, name: 'One', url: 'https://one.wordpress.com' },
+			{ id: 2, name: 'Two', url: 'https://two.wordpress.com' },
+		] );
+		vi.mocked( search ).mockRejectedValueOnce(
+			Object.assign( new Error( 'aborted' ), { name: 'AbortPromptError' } )
+		);
+
+		await expect( resolveSourceSite() ).rejects.toThrow( /No WordPress.com site selected/ );
+	} );
+} );
+
 describe( 'CLI: studio pull-reprint db-apply phase', () => {
 	afterEach( () => {
 		vi.restoreAllMocks();