diff --git a/packages/design-system/organisms/app-shell/AppShell.tsx b/packages/design-system/organisms/app-shell/AppShell.tsx
index c724e4e..bfb2e94 100644
--- a/packages/design-system/organisms/app-shell/AppShell.tsx
+++ b/packages/design-system/organisms/app-shell/AppShell.tsx
@@ -13,6 +13,7 @@ export type AppShellProps = {
     small?: boolean;
     activeGuildId?: string | null;
     guilds?: GuildSlug[];
+    recentGuilds?: string[];
     disableGuildPicker?: boolean;
 };
 
@@ -26,6 +27,7 @@ export const AppShell = (props: AppShellProps) => (
                 guilds={props.guilds || []}
                 activeGuildId={props.activeGuildId || null}
                 user={props.user}
+                recentGuilds={props.recentGuilds}
             />
         ) : (
             <Masthead.Guest />
diff --git a/packages/design-system/organisms/masthead/Authed.tsx b/packages/design-system/organisms/masthead/Authed.tsx
index bb21c09..d25500e 100644
--- a/packages/design-system/organisms/masthead/Authed.tsx
+++ b/packages/design-system/organisms/masthead/Authed.tsx
@@ -22,6 +22,7 @@ type Props = {
     activeGuildId: string | null;
     guilds: GuildSlug[];
     disableGuildPicker?: boolean;
+    recentGuilds: string[];
 };
 
 export const Authed = (props: Props) => {
@@ -65,7 +66,12 @@ export const Authed = (props: Props) => {
                         preferredWidth={560}
                         onExit={() => setServerPopoverState(false)}
                     >
-                        {() => <GuildNav guilds={props.guilds} />}
+                        {() => (
+                            <GuildNav
+                                guilds={props.guilds}
+                                recentGuilds={props.recentGuilds}
+                            />
+                        )}
                     </Popover>
                 </MastheadLeft>
                 <MastheadRight>
diff --git a/packages/web/src/contexts/app-shell/AppShellContext.tsx b/packages/web/src/contexts/app-shell/AppShellContext.tsx
new file mode 100644
index 0000000..13432af
--- /dev/null
+++ b/packages/web/src/contexts/app-shell/AppShellContext.tsx
@@ -0,0 +1,35 @@
+import { AppShellProps } from '@roleypoly/design-system/organisms/app-shell';
+import * as React from 'react';
+import { useRecentGuilds } from '../recent-guilds/RecentGuildsContext';
+import { useSessionContext } from '../session/SessionContext';
+
+type AppShellPropsT = {
+    user: AppShellProps['user'];
+    guilds: AppShellProps['guilds'];
+    recentGuilds: AppShellProps['recentGuilds'];
+};
+
+export const AppShellPropsContext = React.createContext<AppShellPropsT>({
+    user: undefined,
+    guilds: undefined,
+    recentGuilds: [],
+});
+
+export const useAppShellProps = () => React.useContext(AppShellPropsContext);
+
+export const AppShellPropsProvider = (props: { children: React.ReactNode }) => {
+    const { session } = useSessionContext();
+    const { recentGuilds } = useRecentGuilds();
+
+    const appShellProps: AppShellPropsT = {
+        user: session?.user,
+        guilds: session?.guilds,
+        recentGuilds,
+    };
+
+    return (
+        <AppShellPropsContext.Provider value={appShellProps}>
+            {props.children}
+        </AppShellPropsContext.Provider>
+    );
+};
diff --git a/packages/web/src/contexts/recent-guilds/RecentGuildsContext.tsx b/packages/web/src/contexts/recent-guilds/RecentGuildsContext.tsx
new file mode 100644
index 0000000..3319e50
--- /dev/null
+++ b/packages/web/src/contexts/recent-guilds/RecentGuildsContext.tsx
@@ -0,0 +1,59 @@
+import * as React from 'react';
+
+type RecentGuildsT = {
+    recentGuilds: string[];
+    pushRecentGuild: (id: string) => void;
+};
+
+export const RecentGuilds = React.createContext<RecentGuildsT>({
+    recentGuilds: [],
+    pushRecentGuild: () => {},
+});
+
+export const useRecentGuilds = () => React.useContext(RecentGuilds);
+
+const saveState = (state: string[]) => {
+    localStorage.setItem('rp_recent_guilds', JSON.stringify(state));
+};
+
+const pullState = (): string[] => {
+    const rawState = localStorage.getItem('rp_recent_guilds');
+    if (!rawState) {
+        return [];
+    }
+
+    try {
+        return JSON.parse(rawState);
+    } catch (e) {
+        console.warn('RecentGuilds failed to re-hydrate saved state', e);
+        return [];
+    }
+};
+
+export const RecentGuildsProvider = (props: { children: React.ReactNode }) => {
+    const [recentGuilds, setRecentGuilds] = React.useState<string[]>(pullState());
+
+    const recentGuildsData: RecentGuildsT = {
+        recentGuilds,
+        pushRecentGuild: (id: string) => {
+            const nextState = [
+                id,
+                ...recentGuilds.slice(0, 19).filter((guild) => guild !== id),
+            ];
+
+            if (recentGuilds[0] !== id) {
+                setRecentGuilds(nextState);
+            }
+        },
+    };
+
+    React.useEffect(() => {
+        saveState(recentGuilds);
+    }, [recentGuilds]);
+
+    return (
+        <RecentGuilds.Provider value={recentGuildsData}>
+            {props.children}
+        </RecentGuilds.Provider>
+    );
+};
diff --git a/packages/web/src/index.tsx b/packages/web/src/index.tsx
index 7d33083..1b9b869 100644
--- a/packages/web/src/index.tsx
+++ b/packages/web/src/index.tsx
@@ -2,15 +2,32 @@ import React from 'react';
 import ReactDOM from 'react-dom';
 import { AppRouter } from './app-router/AppRouter';
 import { ApiContextProvider } from './contexts/api/ApiContext';
+import { AppShellPropsProvider } from './contexts/app-shell/AppShellContext';
+import { RecentGuildsProvider } from './contexts/recent-guilds/RecentGuildsContext';
 import { SessionContextProvider } from './contexts/session/SessionContext';
 
+const ProviderProvider = (props: {
+    providerChain: typeof ApiContextProvider[];
+    children: React.ReactNode;
+}) => {
+    return props.providerChain.reduceRight(
+        (acc, Provider) => <Provider>{acc}</Provider>,
+        <>{props.children}</>
+    );
+};
+
 ReactDOM.render(
     <React.StrictMode>
-        <ApiContextProvider>
-            <SessionContextProvider>
-                <AppRouter />
-            </SessionContextProvider>
-        </ApiContextProvider>
+        <ProviderProvider
+            providerChain={[
+                ApiContextProvider,
+                SessionContextProvider,
+                RecentGuildsProvider,
+                AppShellPropsProvider,
+            ]}
+        >
+            <AppRouter />
+        </ProviderProvider>
     </React.StrictMode>,
     document.getElementById('root')
 );
diff --git a/packages/web/src/pages/picker.tsx b/packages/web/src/pages/picker.tsx
index 707bd37..d64b207 100644
--- a/packages/web/src/pages/picker.tsx
+++ b/packages/web/src/pages/picker.tsx
@@ -3,6 +3,7 @@ import { RolePickerTemplate } from '@roleypoly/design-system/templates/role-pick
 import { ServerSetupTemplate } from '@roleypoly/design-system/templates/server-setup';
 import { PresentableGuild, RoleUpdate, UserGuildPermissions } from '@roleypoly/types';
 import * as React from 'react';
+import { useRecentGuilds } from '../contexts/recent-guilds/RecentGuildsContext';
 import { useSessionContext } from '../contexts/session/SessionContext';
 import { makeRoleTransactions } from '../utils/roleTransactions';
 
@@ -12,6 +13,7 @@ type PickerProps = {
 
 const Picker = (props: PickerProps) => {
     const { session, authedFetch, isAuthenticated } = useSessionContext();
+    const { pushRecentGuild } = useRecentGuilds();
 
     const [pickerData, setPickerData] = React.useState<PresentableGuild | null | false>(
         null
@@ -32,7 +34,11 @@ const Picker = (props: PickerProps) => {
         };
 
         fetchPickerData();
-    }, [props.serverID, authedFetch]);
+    }, [props.serverID, authedFetch, pushRecentGuild]);
+
+    React.useCallback((serverID) => pushRecentGuild(serverID), [pushRecentGuild])(
+        props.serverID
+    );
 
     if (!isAuthenticated) {
         return <Redirect to={`/auth/login?r=${props.serverID}`} replace />;