diff --git a/packages/design-system/organisms/masthead/Authed.tsx b/packages/design-system/organisms/masthead/Authed.tsx
index 7b176cc..bb21c09 100644
--- a/packages/design-system/organisms/masthead/Authed.tsx
+++ b/packages/design-system/organisms/masthead/Authed.tsx
@@ -32,7 +32,7 @@ export const Authed = (props: Props) => {
         <MastheadBase>
             <MastheadAlignment>
                 <MastheadLeft>
-                    <MastheadA href="/servers">
+                    <MastheadA to="/servers">
                         <DynamicLogomark height={35} />
                     </MastheadA>
                     <InteractionBase
diff --git a/packages/design-system/organisms/masthead/Guest.tsx b/packages/design-system/organisms/masthead/Guest.tsx
index b475fdc..1377dd3 100644
--- a/packages/design-system/organisms/masthead/Guest.tsx
+++ b/packages/design-system/organisms/masthead/Guest.tsx
@@ -14,12 +14,12 @@ export const Guest = () => (
     <MastheadBase>
         <MastheadAlignment>
             <MastheadLeft>
-                <MastheadA href="/">
+                <MastheadA to="/">
                     <DynamicLogotype height={30} />
                 </MastheadA>
             </MastheadLeft>
             <MastheadRight>
-                <MastheadA href="/auth/login">
+                <MastheadA to="/auth/login">
                     <Button size="small">
                         Login{' '}
                         <FaSignInAlt
diff --git a/packages/design-system/organisms/masthead/Masthead.styled.tsx b/packages/design-system/organisms/masthead/Masthead.styled.tsx
index 67ed556..6412de0 100644
--- a/packages/design-system/organisms/masthead/Masthead.styled.tsx
+++ b/packages/design-system/organisms/masthead/Masthead.styled.tsx
@@ -1,3 +1,4 @@
+import { Link } from '@reach/router';
 import { onSmallScreen } from '@roleypoly/design-system/atoms/breakpoints';
 import { palette } from '@roleypoly/design-system/atoms/colors';
 import { transitions } from '@roleypoly/design-system/atoms/timings';
@@ -66,7 +67,7 @@ export const InteractionBase = styled.div<InteractionBaseProps>`
     }
 `;
 
-export const MastheadA = styled.a`
+export const MastheadA = styled(Link)`
     display: flex;
     align-items: center;
     justify-content: center;
diff --git a/packages/web/src/api-context/ApiContext.spec.tsx b/packages/web/src/api-context/ApiContext.spec.tsx
new file mode 100644
index 0000000..2fe5e30
--- /dev/null
+++ b/packages/web/src/api-context/ApiContext.spec.tsx
@@ -0,0 +1,65 @@
+import { render, screen } from '@testing-library/react';
+import * as React from 'react';
+import { ApiContextProvider, useApiContext } from './ApiContext';
+
+const fetchMock = (global.fetch = jest
+    .fn()
+    .mockImplementation(() => ({ json: async () => ({}) })));
+
+const TestComponent = () => {
+    const context = useApiContext();
+
+    React.useEffect(() => {
+        void context.fetch('/not-a-route');
+    });
+
+    return <>{context.apiUrl}</>;
+};
+
+const WrappedTestComponent = () => (
+    <ApiContextProvider>
+        <TestComponent />
+    </ApiContextProvider>
+);
+
+it('correctly does fetch url requests', () => {
+    render(<WrappedTestComponent />);
+
+    expect(fetchMock).toBeCalledWith('http://localhost:6609/not-a-route');
+});
+
+it('sets up api context when localStorage is set', () => {
+    localStorage.setItem('api_url', 'https://abcde.roleypoly.test');
+    render(<WrappedTestComponent />);
+
+    expect(fetchMock).toBeCalledWith('https://abcde.roleypoly.test/not-a-route');
+    expect(screen.getByText('https://abcde.roleypoly.test').innerHTML).toStrictEqual(
+        'https://abcde.roleypoly.test'
+    );
+});
+
+it.each([
+    ['https://next.roleypoly.com/servers', 'https://api-prod.roleypoly.com'],
+    ['https://roleypoly.com/servers', 'https://api-prod.roleypoly.com'],
+    ['https://notroleypolybutclose.com/servers', 'https://api-prod.roleypoly.com'],
+    ['https://myhash.roleypoly.pages.dev/servers', 'https://api-stage.roleypoly.com'],
+    ['http://localhost:6601/servers', 'http://localhost:6609'],
+    ['http://127.0.0.1:6601/servers', 'http://localhost:6609'],
+])('sets up api context based on window.location.href = %s', (inputUrl, outputUrl) => {
+    // @ts-ignore
+    delete window.location;
+    window.location = new URL(inputUrl) as any;
+
+    render(<WrappedTestComponent />);
+
+    expect(fetchMock).toBeCalledWith(`${outputUrl}/not-a-route`);
+    expect(screen.getByText(outputUrl).innerHTML).toStrictEqual(outputUrl);
+});
+
+const originalWindowLocation = window.location;
+
+afterEach(() => {
+    localStorage.clear();
+    fetchMock.mockClear();
+    window.location = originalWindowLocation;
+});
diff --git a/packages/web/src/api-context/ApiContext.tsx b/packages/web/src/api-context/ApiContext.tsx
new file mode 100644
index 0000000..439f9ab
--- /dev/null
+++ b/packages/web/src/api-context/ApiContext.tsx
@@ -0,0 +1,45 @@
+import * as React from 'react';
+import { getDefaultApiUrl } from './getDefaultApiUrl';
+
+type ApiContextData = {
+    apiUrl: string;
+    setApiUrl: (url: string) => void;
+    fetch: (path: string, ...rest: any) => Promise<Response>;
+};
+
+export const ApiContext = React.createContext<ApiContextData>({
+    apiUrl: getDefaultApiUrl(),
+    setApiUrl: () => {},
+    fetch: async () => {
+        return new Response();
+    },
+});
+
+export const useApiContext = () => React.useContext(ApiContext);
+
+export const ApiContextProvider = (props: { children: React.ReactNode }) => {
+    const [apiUrl, setApiUrl] = React.useState(getDefaultApiUrl());
+
+    const apiContextData: ApiContextData = {
+        apiUrl,
+        setApiUrl,
+        fetch: async (path: string, ...rest: any): Promise<Response> => {
+            return fetch(`${apiUrl}${path}`, ...rest);
+        },
+    };
+
+    React.useEffect(() => {
+        const storedApiUrl = localStorage.getItem('api_url');
+        if (storedApiUrl) {
+            setApiUrl(storedApiUrl);
+        }
+    }, []);
+
+    React.useEffect(() => {
+        localStorage.setItem('api_url', apiUrl);
+    }, [apiUrl]);
+
+    return (
+        <ApiContext.Provider value={apiContextData}>{props.children}</ApiContext.Provider>
+    );
+};
diff --git a/packages/web/src/api-context/getDefaultApiUrl.spec.ts b/packages/web/src/api-context/getDefaultApiUrl.spec.ts
new file mode 100644
index 0000000..bdde8d3
--- /dev/null
+++ b/packages/web/src/api-context/getDefaultApiUrl.spec.ts
@@ -0,0 +1,14 @@
+import { getDefaultApiUrl } from './getDefaultApiUrl';
+
+it.each([
+    ['https://next.roleypoly.com/servers', 'https://api-prod.roleypoly.com'],
+    ['https://roleypoly.com/servers', 'https://api-prod.roleypoly.com'],
+    ['https://notroleypolybutclose.com/servers', 'https://api-prod.roleypoly.com'],
+    ['https://myhash.roleypoly.pages.dev/servers', 'https://api-stage.roleypoly.com'],
+    ['http://localhost:6601/servers', 'http://localhost:6609'],
+    ['http://127.0.0.1:6601/servers', 'http://localhost:6609'],
+])('matches %s to %s', (inputUrl, outputUrl) => {
+    const urlHostname = new URL(inputUrl).hostname;
+
+    expect(getDefaultApiUrl(urlHostname)).toStrictEqual(outputUrl);
+});
diff --git a/packages/web/src/api-context/getDefaultApiUrl.ts b/packages/web/src/api-context/getDefaultApiUrl.ts
new file mode 100644
index 0000000..18eba53
--- /dev/null
+++ b/packages/web/src/api-context/getDefaultApiUrl.ts
@@ -0,0 +1,11 @@
+export const getDefaultApiUrl = (host: string = window.location.hostname) => {
+    if (/roleypoly.com$/.test(host)) {
+        return 'https://api-prod.roleypoly.com';
+    } else if (/roleypoly\.pages\.dev$/.test(host)) {
+        return 'https://api-stage.roleypoly.com';
+    } else if (/\blocalhost|127\.0\.0\.1\b/.test(host)) {
+        return 'http://localhost:6609';
+    } else {
+        return 'https://api-prod.roleypoly.com';
+    }
+};
diff --git a/packages/web/src/app-router/AppRouter.tsx b/packages/web/src/app-router/AppRouter.tsx
index f79e6f1..01f752c 100644
--- a/packages/web/src/app-router/AppRouter.tsx
+++ b/packages/web/src/app-router/AppRouter.tsx
@@ -2,6 +2,8 @@ import { Router } from '@reach/router';
 import * as React from 'react';
 
 const LandingPage = React.lazy(() => import('../pages/landing'));
+const DevToolsSetApi = React.lazy(() => import('../pages/dev-tools/set-api'));
+const DevToolsSessionDebug = React.lazy(() => import('../pages/dev-tools/session-debug'));
 
 const RouteWrapper = (props: {
     component: React.LazyExoticComponent<React.ComponentType<any>>;
@@ -17,6 +19,11 @@ export const AppRouter = () => {
     return (
         <Router>
             <RouteWrapper component={LandingPage} path="/" />
+            <RouteWrapper component={DevToolsSetApi} path="/x/dev-tools/set-api" />
+            <RouteWrapper
+                component={DevToolsSessionDebug}
+                path="/x/dev-tools/session-debug"
+            />
         </Router>
     );
 };
diff --git a/packages/web/src/app-router/index.ts b/packages/web/src/app-router/index.ts
deleted file mode 100644
index fda706f..0000000
--- a/packages/web/src/app-router/index.ts
+++ /dev/null
@@ -1 +0,0 @@
-export * from './AppRouter';
diff --git a/packages/web/src/index.tsx b/packages/web/src/index.tsx
index f506f86..bcaef66 100644
--- a/packages/web/src/index.tsx
+++ b/packages/web/src/index.tsx
@@ -1,10 +1,16 @@
 import React from 'react';
 import ReactDOM from 'react-dom';
-import { AppRouter } from './app-router';
+import { ApiContextProvider } from './api-context/ApiContext';
+import { AppRouter } from './app-router/AppRouter';
+import { SessionContextProvider } from './session-context/SessionContext';
 
 ReactDOM.render(
     <React.StrictMode>
-        <AppRouter />
+        <ApiContextProvider>
+            <SessionContextProvider>
+                <AppRouter />
+            </SessionContextProvider>
+        </ApiContextProvider>
     </React.StrictMode>,
     document.getElementById('root')
 );
diff --git a/packages/web/src/pages/dev-tools/session-debug.tsx b/packages/web/src/pages/dev-tools/session-debug.tsx
new file mode 100644
index 0000000..04bb61c
--- /dev/null
+++ b/packages/web/src/pages/dev-tools/session-debug.tsx
@@ -0,0 +1,21 @@
+import { useSessionContext } from '../../session-context/SessionContext';
+
+const SessionDebug = () => {
+    const session = useSessionContext();
+
+    return (
+        <pre>
+            {JSON.stringify(
+                {
+                    isAuthenticated: !!session.session?.user,
+                    user: session.session?.user || null,
+                    guilds: session.session?.guilds || null,
+                },
+                null,
+                '  '
+            )}
+        </pre>
+    );
+};
+
+export default SessionDebug;
diff --git a/packages/web/src/pages/dev-tools/set-api.tsx b/packages/web/src/pages/dev-tools/set-api.tsx
new file mode 100644
index 0000000..a7d817c
--- /dev/null
+++ b/packages/web/src/pages/dev-tools/set-api.tsx
@@ -0,0 +1,51 @@
+import { navigate } from '@reach/router';
+import * as React from 'react';
+import { useApiContext } from '../../api-context/ApiContext';
+
+const SetApi = () => {
+    const apiContext = useApiContext();
+    const [apiField, setApiField] = React.useState(apiContext.apiUrl);
+
+    const setApi = () => {
+        // Clear storage to get rid of old API data
+        localStorage.clear();
+        sessionStorage.clear();
+
+        apiContext.setApiUrl(apiField);
+
+        navigate('/');
+    };
+
+    const quickSettingClick = (url: string) => () => {
+        setApiField(url);
+    };
+
+    return (
+        <div>
+            <div>
+                <input
+                    type="text"
+                    value={apiField}
+                    onChange={(ev) => {
+                        setApiField(ev.target.value);
+                    }}
+                />
+                <button onClick={setApi}>Set &amp; Go</button>
+            </div>
+            <div>
+                Quick Settings:
+                <button onClick={quickSettingClick('https://api-prod.roleypoly.com')}>
+                    Production (api-prod)
+                </button>
+                <button onClick={quickSettingClick('https://api-stage.roleypoly.com')}>
+                    Staging (api-stage)
+                </button>
+                <button onClick={quickSettingClick('http://localhost:6609')}>
+                    Local (:6609)
+                </button>
+            </div>
+        </div>
+    );
+};
+
+export default SetApi;
diff --git a/packages/web/src/session-context/SessionContext.tsx b/packages/web/src/session-context/SessionContext.tsx
new file mode 100644
index 0000000..0c859b5
--- /dev/null
+++ b/packages/web/src/session-context/SessionContext.tsx
@@ -0,0 +1,113 @@
+import { SessionData } from '@roleypoly/types';
+import * as React from 'react';
+import { useApiContext } from '../api-context/ApiContext';
+
+type SessionContextT = {
+    session?: Omit<Partial<SessionData>, 'tokens'>;
+    setSession: (session?: SessionContextT['session']) => void;
+    authedFetch: (url: string, opts?: RequestInit) => Promise<Response>;
+};
+
+const SessionContext = React.createContext<SessionContextT>({
+    setSession: () => {},
+    authedFetch: async () => {
+        return new Response();
+    },
+});
+
+export const useSessionContext = () => React.useContext(SessionContext);
+
+export const SessionContextProvider = (props: { children: React.ReactNode }) => {
+    const api = useApiContext();
+    const [session, setSession] = React.useState<SessionContextT['session']>(undefined);
+
+    const sessionContextValue: SessionContextT = React.useMemo(
+        () => ({
+            session,
+            setSession,
+            authedFetch: (url: string, opts?: RequestInit) => {
+                return api.fetch(url, {
+                    ...opts,
+                    headers: {
+                        ...opts?.headers,
+                        authorization: session?.sessionID
+                            ? `Bearer ${session?.sessionID}`
+                            : undefined,
+                    },
+                });
+            },
+        }),
+        [session, api]
+    );
+
+    React.useEffect(() => {
+        // No session is set, do we have one available?
+        if (!sessionContextValue.session || !sessionContextValue.session.sessionID) {
+            // We may have the full state in session storage...
+            const storedSessionData = sessionStorage.getItem('rp_session_data');
+            if (storedSessionData) {
+                try {
+                    setSession(JSON.parse(storedSessionData));
+                    return;
+                } catch (e) {
+                    // Oops, this data is wrong.
+                }
+            }
+
+            // But if not, we have the key, maybe?
+            const storedSessionID = localStorage.getItem('rp_session_key');
+            if (storedSessionID && storedSessionID !== '') {
+                setSession({ sessionID: storedSessionID });
+                return;
+            }
+
+            // If we hit here, we're definitely not authenticated.
+            return;
+        }
+
+        // If a session is set and it's not stored, set it now.
+        if (
+            localStorage.getItem('rp_session_key') !==
+            sessionContextValue.session.sessionID
+        ) {
+            localStorage.setItem(
+                'rp_session_key',
+                sessionContextValue.session.sessionID || ''
+            );
+        }
+
+        // Session is set, but we don't have data. Server sup?
+        if (sessionContextValue.session.sessionID && !sessionContextValue.session.user) {
+            const syncSession = async () => {
+                const response = await sessionContextValue.authedFetch('/get-session');
+                if (response.status !== 200) {
+                    console.error('get-session failed', { response });
+                    clearSessionData();
+                    return;
+                }
+
+                const serverSession: SessionContextT['session'] = await response.json();
+
+                setSession(serverSession);
+                sessionStorage.setItem('rp_session_data', JSON.stringify(serverSession));
+            };
+
+            syncSession();
+        }
+    }, [
+        sessionContextValue.session?.user,
+        sessionContextValue.session?.sessionID,
+        sessionContextValue,
+    ]);
+
+    return (
+        <SessionContext.Provider value={sessionContextValue}>
+            {props.children}
+        </SessionContext.Provider>
+    );
+};
+
+const clearSessionData = () => {
+    sessionStorage.removeItem('rp_session_data');
+    localStorage.removeItem('rp_session_key');
+};