diff --git a/common/lib/sort-sites.ts b/common/lib/sort-sites.ts
index 27aa26c94d..d1aa919909 100644
--- a/common/lib/sort-sites.ts
+++ b/common/lib/sort-sites.ts
@@ -1,3 +1,18 @@
-export function sortSites< T extends { name: string } >( sites: T[] ): T[] {
-	return sites.sort( ( a, b ) => a.name.localeCompare( b.name, undefined, { numeric: true } ) );
+export function sortSites< T extends { name: string; sortOrder?: number } >( sites: T[] ): T[] {
+	return sites.sort( ( a, b ) => {
+		// If both have sortOrder, sort by sortOrder
+		if ( a.sortOrder !== undefined && b.sortOrder !== undefined ) {
+			return a.sortOrder - b.sortOrder;
+		}
+		// If only a has sortOrder, a comes first
+		if ( a.sortOrder !== undefined ) {
+			return -1;
+		}
+		// If only b has sortOrder, b comes first
+		if ( b.sortOrder !== undefined ) {
+			return 1;
+		}
+		// Neither has sortOrder, sort by name
+		return a.name.localeCompare( b.name, undefined, { numeric: true } );
+	} );
 }
diff --git a/common/lib/tests/sort-sites.test.ts b/common/lib/tests/sort-sites.test.ts
index 3d41b2d470..231fa05191 100644
--- a/common/lib/tests/sort-sites.test.ts
+++ b/common/lib/tests/sort-sites.test.ts
@@ -20,4 +20,36 @@ describe( 'sortSites', () => {
 			'Tristan',
 		] );
 	} );
+
+	it( 'should sort sites by sortOrder when available', () => {
+		const sites = [
+			{ name: 'Charlie', sortOrder: 3000 },
+			{ name: 'Alpha', sortOrder: 1000 },
+			{ name: 'Bravo', sortOrder: 2000 },
+		] as SiteDetails[];
+
+		const sortedSites = sortSites( sites );
+
+		expect( sortedSites.map( ( site ) => site.name ) ).toEqual( [ 'Alpha', 'Bravo', 'Charlie' ] );
+	} );
+
+	it( 'should prioritize sortOrder over name', () => {
+		const sites = [
+			{ name: 'Zulu', sortOrder: 3000 },
+			{ name: 'Charlie' },
+			{ name: 'Alpha', sortOrder: 1000 },
+			{ name: 'Bravo' },
+			{ name: 'Beta', sortOrder: 2000 },
+		] as SiteDetails[];
+
+		const sortedSites = sortSites( sites );
+
+		expect( sortedSites.map( ( site ) => site.name ) ).toEqual( [
+			'Alpha',
+			'Beta',
+			'Zulu',
+			'Bravo',
+			'Charlie',
+		] );
+	} );
 } );
diff --git a/src/components/site-menu.tsx b/src/components/site-menu.tsx
index 542a317f03..76d0164746 100644
--- a/src/components/site-menu.tsx
+++ b/src/components/site-menu.tsx
@@ -2,7 +2,8 @@ import * as Sentry from '@sentry/electron/renderer';
 import { speak } from '@wordpress/a11y';
 import { Spinner } from '@wordpress/components';
 import { __, sprintf } from '@wordpress/i18n';
-import { useEffect } from 'react';
+import { Icon, dragHandle } from '@wordpress/icons';
+import { useEffect, useState } from 'react';
 import { XDebugIcon } from 'src/components/icons/xdebug-icon';
 import { Tooltip } from 'src/components/tooltip';
 import { useSyncSites } from 'src/hooks/sync-sites';
@@ -46,6 +47,7 @@ function ButtonToRun( {
 	const classCircle = `rounded-full`;
 	const triangle = (
 		<svg
+			aria-hidden="true"
 			width="8"
 			height="10"
 			viewBox="0 0 8 10"
@@ -63,7 +65,14 @@ function ButtonToRun( {
 	);
 
 	const rectangle = (
-		<svg width="10" height="10" viewBox="0 0 10 10" fill="none" xmlns="http://www.w3.org/2000/svg">
+		<svg
+			aria-hidden="true"
+			width="10"
+			height="10"
+			viewBox="0 0 10 10"
+			fill="none"
+			xmlns="http://www.w3.org/2000/svg"
+		>
 			<path
 				d="M0.25 2C0.25 1.0335 1.0335 0.25 2 0.25H8C8.9665 0.25 9.75 1.0335 9.75 2V8C9.75 8.9665 8.9665 9.75 8 9.75H2C1.0335 9.75 0.25 8.9665 0.25 8V2Z"
 				fill="#FF8085"
@@ -82,6 +91,7 @@ function ButtonToRun( {
 	return (
 		<Tooltip text={ tooltipText }>
 			<button
+				type="button"
 				aria-disabled={ loadingServer[ id ] }
 				onClick={ () => {
 					if ( loadingServer[ id ] ) {
@@ -132,7 +142,23 @@ function ButtonToRun( {
 		</Tooltip>
 	);
 }
-function SiteItem( { site }: { site: SiteDetails } ) {
+function SiteItem( {
+	site,
+	index,
+	onDragStart,
+	onDragOver,
+	onDrop,
+	onDragEnd,
+	isDragOver,
+}: {
+	site: SiteDetails;
+	index: number;
+	onDragStart: ( e: React.DragEvent, index: number ) => void;
+	onDragOver: ( e: React.DragEvent, index: number ) => void;
+	onDrop: ( e: React.DragEvent, index: number ) => void;
+	onDragEnd: () => void;
+	isDragOver: boolean;
+} ) {
 	const { selectedSite, setSelectedSiteId, loadingServer, isSiteDeleting } = useSiteDetails();
 	const isSelected = site === selectedSite;
 	const { isSiteImporting, isSiteExporting } = useImportExport();
@@ -148,7 +174,7 @@ function SiteItem( { site }: { site: SiteDetails } ) {
 	const showSpinner =
 		site.isAddingSite || isImporting || isPulling || isPushing || isExporting || isDeleting;
 
-	let tooltipText;
+	let tooltipText: string;
 	if ( site.isAddingSite ) {
 		tooltipText = __( 'Adding' );
 	} else if ( isImporting ) {
@@ -184,13 +210,21 @@ function SiteItem( { site }: { site: SiteDetails } ) {
 	return (
 		<li
 			className={ cx(
-				'flex flex-row min-w-[168px] h-8 hover:bg-[#ffffff0C] rounded transition-all ms-1',
+				'flex flex-row min-w-[168px] h-8 hover:bg-[#ffffff0C] rounded transition-all ms-1 items-center',
 				isMac() ? 'me-5' : 'me-4',
-				isSelected && 'bg-[#ffffff19] hover:bg-[#ffffff19]'
+				isSelected && 'bg-[#ffffff19] hover:bg-[#ffffff19]',
+				isDragOver && 'bg-[#ffffff26]'
 			) }
 			onContextMenu={ handleContextMenu }
+			draggable
+			onDragStart={ ( e ) => onDragStart( e, index ) }
+			onDragOver={ ( e ) => onDragOver( e, index ) }
+			onDrop={ ( e ) => onDrop( e, index ) }
+			onDragEnd={ onDragEnd }
 		>
+			<Icon icon={ dragHandle } className="fill-white" />
 			<button
+				type="button"
 				className="p-2 text-xs rounded-tl rounded-bl whitespace-nowrap overflow-hidden text-ellipsis w-full text-left rtl:text-right focus-visible:outline-none focus-visible:ring-1 focus-visible:ring-a8c-blue-50"
 				onClick={ () => {
 					setSelectedSiteId( site.id );
@@ -201,7 +235,7 @@ function SiteItem( { site }: { site: SiteDetails } ) {
 			{ showSpinner ? (
 				<Tooltip text={ tooltipText }>
 					<div className="grid place-items-center">
-						<Spinner className="!w-2.5 !h-2.5 !top-[6px] !mr-2 [&>circle]:stroke-a8c-gray-70" />
+						<Spinner className="!w-2.5 !h-2.5 !mt-0 !mr-2 [&>circle]:stroke-a8c-gray-70" />
 					</div>
 				</Tooltip>
 			) : (
@@ -212,11 +246,63 @@ function SiteItem( { site }: { site: SiteDetails } ) {
 }
 
 export default function SiteMenu( { className }: SiteMenuProps ) {
-	const { sites, selectedSite, setSelectedSiteId, startServer, stopServer, setIsEditModalOpen } =
-		useSiteDetails();
+	const {
+		sites,
+		selectedSite,
+		setSelectedSiteId,
+		startServer,
+		stopServer,
+		setIsEditModalOpen,
+		reorderSites,
+	} = useSiteDetails();
 	const { setSelectedTab } = useContentTabs();
 	const { handleDeleteSite } = useDeleteSite();
 	const { data: editor } = useGetUserEditorQuery();
+	const [ draggedIndex, setDraggedIndex ] = useState< number | null >( null );
+	const [ dragOverIndex, setDragOverIndex ] = useState< number | null >( null );
+
+	const handleDragStart = ( e: React.DragEvent, index: number ) => {
+		setDraggedIndex( index );
+		e.dataTransfer.effectAllowed = 'move';
+	};
+
+	const handleDragOver = ( e: React.DragEvent, index: number ) => {
+		e.preventDefault();
+		e.dataTransfer.dropEffect = 'move';
+		if ( draggedIndex !== null && draggedIndex !== index ) {
+			setDragOverIndex( index );
+		}
+	};
+
+	const reorderSitesToNewPositions = ( newSites: SiteDetails[] ) => {
+		const updates = newSites.map( ( site, index ) => ( {
+			siteId: site.id,
+			sortOrder: ( index + 1 ) * 1000,
+		} ) );
+
+		reorderSites( updates ).catch( ( error ) => {
+			console.error( 'Failed to save site order:', error );
+		} );
+	};
+
+	const handleDrop = ( e: React.DragEvent, targetIndex: number ) => {
+		e.preventDefault();
+		setDragOverIndex( null );
+		if ( draggedIndex === null || draggedIndex === targetIndex ) {
+			return;
+		}
+
+		const newSites = [ ...sites ];
+		const [ movedSite ] = newSites.splice( draggedIndex, 1 );
+		newSites.splice( targetIndex, 0, movedSite );
+
+		reorderSitesToNewPositions( newSites );
+	};
+
+	const handleDragEnd = () => {
+		setDraggedIndex( null );
+		setDragOverIndex( null );
+	};
 
 	useEffect( () => {
 		const unsubscribe = window.ipcListener.subscribe(
@@ -306,9 +392,24 @@ export default function SiteMenu( { className }: SiteMenuProps ) {
 			) }
 		>
 			<ul className="pt-px">
-				{ sites.map( ( site ) => (
-					<SiteItem key={ site.id } site={ site } />
+				{ sites.map( ( site, index ) => (
+					<SiteItem
+						key={ site.id }
+						site={ site }
+						index={ index }
+						onDragStart={ handleDragStart }
+						onDragOver={ handleDragOver }
+						onDrop={ handleDrop }
+						onDragEnd={ handleDragEnd }
+						isDragOver={ dragOverIndex === index }
+					/>
 				) ) }
+				{ /* Drop zone for dragging to bottom of list */ }
+				<li
+					className="h-8"
+					onDragOver={ ( e ) => handleDragOver( e, sites.length ) }
+					onDrop={ ( e ) => handleDrop( e, sites.length ) }
+				/>
 			</ul>
 		</nav>
 	);
diff --git a/src/hooks/use-site-details.tsx b/src/hooks/use-site-details.tsx
index f21c0b3bbe..81d7ed8df2 100644
--- a/src/hooks/use-site-details.tsx
+++ b/src/hooks/use-site-details.tsx
@@ -23,6 +23,7 @@ import type { Blueprint } from 'src/stores/wpcom-api';
 interface SiteDetailsContext {
 	selectedSite: SiteDetails | null;
 	updateSite: ( site: SiteDetails, wpVersion?: string ) => Promise< void >;
+	reorderSites: ( updates: { siteId: string; sortOrder: number }[] ) => Promise< void >;
 	sites: SiteDetails[];
 	setSelectedSiteId: ( selectedSiteId: string ) => void;
 	createSite: (
@@ -54,6 +55,7 @@ interface SiteDetailsContext {
 const defaultContext: SiteDetailsContext = {
 	selectedSite: null,
 	updateSite: async () => undefined,
+	reorderSites: async () => undefined,
 	sites: [],
 	siteCreationMessages: {},
 	setSelectedSiteId: () => undefined,
@@ -355,7 +357,7 @@ export function SiteDetailsProvider( { children }: SiteDetailsProviderProps ) {
 				} );
 				setSites( ( prevData ) =>
 					sortSites( [
-						...prevData.filter( ( site ) => site.id !== tempSiteId ),
+						...prevData.filter( ( site ) => site.id !== tempSiteId && site.id !== newSite.id ),
 						{ ...newSite, isAddingSite: true },
 					] )
 				);
@@ -392,6 +394,12 @@ export function SiteDetailsProvider( { children }: SiteDetailsProviderProps ) {
 		setSites( updatedSites );
 	}, [] );
 
+	const reorderSites = useCallback( async ( updates: { siteId: string; sortOrder: number }[] ) => {
+		await getIpcApi().updateSitesSortOrder( updates );
+		const updatedSites = await getIpcApi().getSiteDetails();
+		setSites( updatedSites );
+	}, [] );
+
 	const startServer = useCallback(
 		async ( id: string ) => {
 			toggleLoadingServerForSite( id );
@@ -518,6 +526,7 @@ export function SiteDetailsProvider( { children }: SiteDetailsProviderProps ) {
 			setSelectedSiteId,
 			createSite,
 			updateSite,
+			reorderSites,
 			startServer,
 			stopServer,
 			stopAllRunningSites,
@@ -538,6 +547,7 @@ export function SiteDetailsProvider( { children }: SiteDetailsProviderProps ) {
 			setSelectedSiteId,
 			createSite,
 			updateSite,
+			reorderSites,
 			startServer,
 			stopServer,
 			stopAllRunningSites,
diff --git a/src/ipc-handlers.ts b/src/ipc-handlers.ts
index 2431f75d4a..775e38bd0b 100644
--- a/src/ipc-handlers.ts
+++ b/src/ipc-handlers.ts
@@ -1408,3 +1408,25 @@ export async function setWindowControlVisibility( event: IpcMainInvokeEvent, vis
 		parentWindow.setWindowButtonVisibility( visible );
 	}
 }
+
+export async function updateSitesSortOrder(
+	event: IpcMainInvokeEvent,
+	updates: { siteId: string; sortOrder: number }[]
+): Promise< void > {
+	try {
+		await lockAppdata();
+		const userData = await loadUserData();
+
+		const updatedSites = userData.sites.map( ( site ) => {
+			const update = updates.find( ( u ) => u.siteId === site.id );
+			if ( update ) {
+				return { ...site, sortOrder: update.sortOrder };
+			}
+			return site;
+		} );
+
+		await saveUserData( { ...userData, sites: updatedSites } );
+	} finally {
+		await unlockAppdata();
+	}
+}
diff --git a/src/ipc-types.d.ts b/src/ipc-types.d.ts
index 0cfc231cbb..46a398b09f 100644
--- a/src/ipc-types.d.ts
+++ b/src/ipc-types.d.ts
@@ -31,6 +31,7 @@ interface StoppedSiteDetails {
 	autoStart?: boolean;
 	latestCliPid?: number;
 	enableXdebug?: boolean;
+	sortOrder?: number;
 }
 
 interface StartedSiteDetails extends StoppedSiteDetails {
diff --git a/src/preload.ts b/src/preload.ts
index ab6f4e37b3..9813878649 100644
--- a/src/preload.ts
+++ b/src/preload.ts
@@ -148,6 +148,7 @@ const api: IpcApi = {
 	showSiteContextMenu: ( context ) => ipcRendererSend( 'showSiteContextMenu', context ),
 	setWindowControlVisibility: ( visible ) =>
 		ipcRendererInvoke( 'setWindowControlVisibility', visible ),
+	updateSitesSortOrder: ( updates ) => ipcRendererInvoke( 'updateSitesSortOrder', updates ),
 	isStudioCliInstalled: () => ipcRendererInvoke( 'isStudioCliInstalled' ),
 	installStudioCli: () => ipcRendererInvoke( 'installStudioCli' ),
 	uninstallStudioCli: () => ipcRendererInvoke( 'uninstallStudioCli' ),
diff --git a/src/storage/user-data.ts b/src/storage/user-data.ts
index da35a653a2..b4596eee22 100644
--- a/src/storage/user-data.ts
+++ b/src/storage/user-data.ts
@@ -167,6 +167,7 @@ function toDiskFormat( { sites, ...rest }: UserData ): PersistedUserData {
 				autoStart,
 				latestCliPid,
 				enableXdebug,
+				sortOrder,
 			} ) => {
 				// No object spreading allowed. TypeScript's structural typing is too permissive and
 				// will permit us to persist properties that aren't in the type definition.
@@ -184,6 +185,7 @@ function toDiskFormat( { sites, ...rest }: UserData ): PersistedUserData {
 					autoStart,
 					latestCliPid,
 					enableXdebug,
+					sortOrder,
 					themeDetails: {
 						name: themeDetails?.name || '',
 						path: themeDetails?.path || '',