diff --git a/web/src/admin/Routes.ts b/web/src/admin/Routes.ts
index f6df48cbbf..a08d375434 100644
--- a/web/src/admin/Routes.ts
+++ b/web/src/admin/Routes.ts
@@ -1,155 +1,266 @@
 import "@goauthentik/admin/admin-overview/AdminOverviewPage";
-import { ID_REGEX, Route, SLUG_REGEX, UUID_REGEX } from "@goauthentik/elements/router/Route";
+import { ID_REGEX, SLUG_REGEX, UUID_REGEX } from "@goauthentik/elements/router/Route";
+import { RawRoute, makeRoute } from "@goauthentik/elements/router/routeUtils";
 
 import { html } from "lit";
 
-export const ROUTES: Route[] = [
+export const _ROUTES: RawRoute[] = [
     // Prevent infinite Shell loops
-    new Route(new RegExp("^/$")).redirect("/administration/overview"),
-    new Route(new RegExp("^#.*")).redirect("/administration/overview"),
-    new Route(new RegExp("^/library$")).redirect("/if/user/", true),
+    ["^/$", "/administration/overview"],
+    ["^#.*", "/administration/overview"],
+    ["^/library$", ["/if/user/", true]],
     // statically imported since this is the default route
-    new Route(new RegExp("^/administration/overview$"), async () => {
-        return html`<ak-admin-overview></ak-admin-overview>`;
-    }),
-    new Route(new RegExp("^/administration/dashboard/users$"), async () => {
-        await import("@goauthentik/admin/admin-overview/DashboardUserPage");
-        return html`<ak-admin-dashboard-users></ak-admin-dashboard-users>`;
-    }),
-    new Route(new RegExp("^/administration/system-tasks$"), async () => {
-        await import("@goauthentik/admin/system-tasks/SystemTaskListPage");
-        return html`<ak-system-task-list></ak-system-task-list>`;
-    }),
-    new Route(new RegExp("^/core/providers$"), async () => {
-        await import("@goauthentik/admin/providers/ProviderListPage");
-        return html`<ak-provider-list></ak-provider-list>`;
-    }),
-    new Route(new RegExp(`^/core/providers/(?<id>${ID_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/providers/ProviderViewPage");
-        return html`<ak-provider-view .providerID=${parseInt(args.id, 10)}></ak-provider-view>`;
-    }),
-    new Route(new RegExp("^/core/applications$"), async () => {
-        await import("@goauthentik/admin/applications/ApplicationListPage");
-        return html`<ak-application-list></ak-application-list>`;
-    }),
-    new Route(new RegExp(`^/core/applications/(?<slug>${SLUG_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/applications/ApplicationViewPage");
-        return html`<ak-application-view .applicationSlug=${args.slug}></ak-application-view>`;
-    }),
-    new Route(new RegExp("^/core/sources$"), async () => {
-        await import("@goauthentik/admin/sources/SourceListPage");
-        return html`<ak-source-list></ak-source-list>`;
-    }),
-    new Route(new RegExp(`^/core/sources/(?<slug>${SLUG_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/sources/SourceViewPage");
-        return html`<ak-source-view .sourceSlug=${args.slug}></ak-source-view>`;
-    }),
-    new Route(new RegExp("^/core/property-mappings$"), async () => {
-        await import("@goauthentik/admin/property-mappings/PropertyMappingListPage");
-        return html`<ak-property-mapping-list></ak-property-mapping-list>`;
-    }),
-    new Route(new RegExp("^/core/tokens$"), async () => {
-        await import("@goauthentik/admin/tokens/TokenListPage");
-        return html`<ak-token-list></ak-token-list>`;
-    }),
-    new Route(new RegExp("^/core/brands"), async () => {
-        await import("@goauthentik/admin/brands/BrandListPage");
-        return html`<ak-brand-list></ak-brand-list>`;
-    }),
-    new Route(new RegExp("^/policy/policies$"), async () => {
-        await import("@goauthentik/admin/policies/PolicyListPage");
-        return html`<ak-policy-list></ak-policy-list>`;
-    }),
-    new Route(new RegExp("^/policy/reputation$"), async () => {
-        await import("@goauthentik/admin/policies/reputation/ReputationListPage");
-        return html`<ak-policy-reputation-list></ak-policy-reputation-list>`;
-    }),
-    new Route(new RegExp("^/identity/groups$"), async () => {
-        await import("@goauthentik/admin/groups/GroupListPage");
-        return html`<ak-group-list></ak-group-list>`;
-    }),
-    new Route(new RegExp(`^/identity/groups/(?<uuid>${UUID_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/groups/GroupViewPage");
-        return html`<ak-group-view .groupId=${args.uuid}></ak-group-view>`;
-    }),
-    new Route(new RegExp("^/identity/users$"), async () => {
-        await import("@goauthentik/admin/users/UserListPage");
-        return html`<ak-user-list></ak-user-list>`;
-    }),
-    new Route(new RegExp(`^/identity/users/(?<id>${ID_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/users/UserViewPage");
-        return html`<ak-user-view .userId=${parseInt(args.id, 10)}></ak-user-view>`;
-    }),
-    new Route(new RegExp("^/identity/roles$"), async () => {
-        await import("@goauthentik/admin/roles/RoleListPage");
-        return html`<ak-role-list></ak-role-list>`;
-    }),
-    new Route(new RegExp(`^/identity/roles/(?<id>${UUID_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/roles/RoleViewPage");
-        return html`<ak-role-view roleId=${args.id}></ak-role-view>`;
-    }),
-    new Route(new RegExp("^/flow/stages/invitations$"), async () => {
-        await import("@goauthentik/admin/stages/invitation/InvitationListPage");
-        return html`<ak-stage-invitation-list></ak-stage-invitation-list>`;
-    }),
-    new Route(new RegExp("^/flow/stages/prompts$"), async () => {
-        await import("@goauthentik/admin/stages/prompt/PromptListPage");
-        return html`<ak-stage-prompt-list></ak-stage-prompt-list>`;
-    }),
-    new Route(new RegExp("^/flow/stages$"), async () => {
-        await import("@goauthentik/admin/stages/StageListPage");
-        return html`<ak-stage-list></ak-stage-list>`;
-    }),
-    new Route(new RegExp("^/flow/flows$"), async () => {
-        await import("@goauthentik/admin/flows/FlowListPage");
-        return html`<ak-flow-list></ak-flow-list>`;
-    }),
-    new Route(new RegExp(`^/flow/flows/(?<slug>${SLUG_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/flows/FlowViewPage");
-        return html`<ak-flow-view .flowSlug=${args.slug}></ak-flow-view>`;
-    }),
-    new Route(new RegExp("^/events/log$"), async () => {
-        await import("@goauthentik/admin/events/EventListPage");
-        return html`<ak-event-list></ak-event-list>`;
-    }),
-    new Route(new RegExp(`^/events/log/(?<id>${UUID_REGEX})$`), async (args) => {
-        await import("@goauthentik/admin/events/EventViewPage");
-        return html`<ak-event-view .eventID=${args.id}></ak-event-view>`;
-    }),
-    new Route(new RegExp("^/events/transports$"), async () => {
-        await import("@goauthentik/admin/events/TransportListPage");
-        return html`<ak-event-transport-list></ak-event-transport-list>`;
-    }),
-    new Route(new RegExp("^/events/rules$"), async () => {
-        await import("@goauthentik/admin/events/RuleListPage");
-        return html`<ak-event-rule-list></ak-event-rule-list>`;
-    }),
-    new Route(new RegExp("^/outpost/outposts$"), async () => {
-        await import("@goauthentik/admin/outposts/OutpostListPage");
-        return html`<ak-outpost-list></ak-outpost-list>`;
-    }),
-    new Route(new RegExp("^/outpost/integrations$"), async () => {
-        await import("@goauthentik/admin/outposts/ServiceConnectionListPage");
-        return html`<ak-outpost-service-connection-list></ak-outpost-service-connection-list>`;
-    }),
-    new Route(new RegExp("^/crypto/certificates$"), async () => {
-        await import("@goauthentik/admin/crypto/CertificateKeyPairListPage");
-        return html`<ak-crypto-certificate-list></ak-crypto-certificate-list>`;
-    }),
-    new Route(new RegExp("^/admin/settings$"), async () => {
-        await import("@goauthentik/admin/admin-settings/AdminSettingsPage");
-        return html`<ak-admin-settings></ak-admin-settings>`;
-    }),
-    new Route(new RegExp("^/blueprints/instances$"), async () => {
-        await import("@goauthentik/admin/blueprints/BlueprintListPage");
-        return html`<ak-blueprint-list></ak-blueprint-list>`;
-    }),
-    new Route(new RegExp("^/debug$"), async () => {
-        await import("@goauthentik/admin/DebugPage");
-        return html`<ak-admin-debug-page></ak-admin-debug-page>`;
-    }),
-    new Route(new RegExp("^/enterprise/licenses$"), async () => {
-        await import("@goauthentik/admin/enterprise/EnterpriseLicenseListPage");
-        return html`<ak-enterprise-license-list></ak-enterprise-license-list>`;
-    }),
+    [
+        "^/administration/overview$",
+        async () => {
+            return html`<ak-admin-overview></ak-admin-overview>`;
+        },
+    ],
+    [
+        "^/administration/dashboard/users$",
+        async () => {
+            await import("@goauthentik/admin/admin-overview/DashboardUserPage");
+            return html`<ak-admin-dashboard-users></ak-admin-dashboard-users>`;
+        },
+    ],
+    [
+        "^/administration/system-tasks$",
+        async () => {
+            await import("@goauthentik/admin/system-tasks/SystemTaskListPage");
+            return html`<ak-system-task-list></ak-system-task-list>`;
+        },
+    ],
+    [
+        "^/core/providers$",
+        async () => {
+            await import("@goauthentik/admin/providers/ProviderListPage");
+            return html`<ak-provider-list></ak-provider-list>`;
+        },
+    ],
+    [
+        `^/core/providers/(?<id>${ID_REGEX}])$`,
+        async (args) => {
+            await import("@goauthentik/admin/providers/ProviderViewPage");
+            return html`<ak-provider-view .providerID=${parseInt(args.id, 10)}></ak-provider-view>`;
+        },
+    ],
+    [
+        "^/core/applications$",
+        async () => {
+            await import("@goauthentik/admin/applications/ApplicationListPage");
+            return html`<ak-application-list></ak-application-list>`;
+        },
+    ],
+    [
+        `^/core/applications/(?<slug>${SLUG_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/applications/ApplicationViewPage");
+            return html`<ak-application-view .applicationSlug=${args.slug}></ak-application-view>`;
+        },
+    ],
+    [
+        "^/core/sources$",
+        async () => {
+            await import("@goauthentik/admin/sources/SourceListPage");
+            return html`<ak-source-list></ak-source-list>`;
+        },
+    ],
+    [
+        `^/core/sources/(?<slug>${SLUG_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/sources/SourceViewPage");
+            return html`<ak-source-view .sourceSlug=${args.slug}></ak-source-view>`;
+        },
+    ],
+    [
+        "^/core/property-mappings$",
+        async () => {
+            await import("@goauthentik/admin/property-mappings/PropertyMappingListPage");
+            return html`<ak-property-mapping-list></ak-property-mapping-list>`;
+        },
+    ],
+    [
+        "^/core/tokens$",
+        async () => {
+            await import("@goauthentik/admin/tokens/TokenListPage");
+            return html`<ak-token-list></ak-token-list>`;
+        },
+    ],
+    [
+        "^/core/brands",
+        async () => {
+            await import("@goauthentik/admin/brands/BrandListPage");
+            return html`<ak-brand-list></ak-brand-list>`;
+        },
+    ],
+    [
+        "^/policy/policies$",
+        async () => {
+            await import("@goauthentik/admin/policies/PolicyListPage");
+            return html`<ak-policy-list></ak-policy-list>`;
+        },
+    ],
+    [
+        "^/policy/reputation$",
+        async () => {
+            await import("@goauthentik/admin/policies/reputation/ReputationListPage");
+            return html`<ak-policy-reputation-list></ak-policy-reputation-list>`;
+        },
+    ],
+    [
+        "^/identity/groups$",
+        async () => {
+            await import("@goauthentik/admin/groups/GroupListPage");
+            return html`<ak-group-list></ak-group-list>`;
+        },
+    ],
+    [
+        `^/identity/groups/(?<uuid>${UUID_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/groups/GroupViewPage");
+            return html`<ak-group-view .groupId=${args.uuid}></ak-group-view>`;
+        },
+    ],
+    [
+        "^/identity/users$",
+        async () => {
+            await import("@goauthentik/admin/users/UserListPage");
+            return html`<ak-user-list></ak-user-list>`;
+        },
+    ],
+    [
+        `^/identity/users/(?<id>${ID_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/users/UserViewPage");
+            return html`<ak-user-view .userId=${parseInt(args.id, 10)}></ak-user-view>`;
+        },
+    ],
+    [
+        "^/identity/roles$",
+        async () => {
+            await import("@goauthentik/admin/roles/RoleListPage");
+            return html`<ak-role-list></ak-role-list>`;
+        },
+    ],
+    [
+        `^/identity/roles/(?<id>${UUID_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/roles/RoleViewPage");
+            return html`<ak-role-view roleId=${args.id}></ak-role-view>`;
+        },
+    ],
+    [
+        "^/flow/stages/invitations$",
+        async () => {
+            await import("@goauthentik/admin/stages/invitation/InvitationListPage");
+            return html`<ak-stage-invitation-list></ak-stage-invitation-list>`;
+        },
+    ],
+    [
+        "^/flow/stages/prompts$",
+        async () => {
+            await import("@goauthentik/admin/stages/prompt/PromptListPage");
+            return html`<ak-stage-prompt-list></ak-stage-prompt-list>`;
+        },
+    ],
+    [
+        "^/flow/stages$",
+        async () => {
+            await import("@goauthentik/admin/stages/StageListPage");
+            return html`<ak-stage-list></ak-stage-list>`;
+        },
+    ],
+    [
+        "^/flow/flows$",
+        async () => {
+            await import("@goauthentik/admin/flows/FlowListPage");
+            return html`<ak-flow-list></ak-flow-list>`;
+        },
+    ],
+    [
+        `^/flow/flows/(?<slug>${SLUG_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/flows/FlowViewPage");
+            return html`<ak-flow-view .flowSlug=${args.slug}></ak-flow-view>`;
+        },
+    ],
+    [
+        "^/events/log$",
+        async () => {
+            await import("@goauthentik/admin/events/EventListPage");
+            return html`<ak-event-list></ak-event-list>`;
+        },
+    ],
+    [
+        `^/events/log/(?<id>${UUID_REGEX})$`,
+        async (args) => {
+            await import("@goauthentik/admin/events/EventViewPage");
+            return html`<ak-event-view .eventID=${args.id}></ak-event-view>`;
+        },
+    ],
+    [
+        "^/events/transports$",
+        async () => {
+            await import("@goauthentik/admin/events/TransportListPage");
+            return html`<ak-event-transport-list></ak-event-transport-list>`;
+        },
+    ],
+    [
+        "^/events/rules$",
+        async () => {
+            await import("@goauthentik/admin/events/RuleListPage");
+            return html`<ak-event-rule-list></ak-event-rule-list>`;
+        },
+    ],
+    [
+        "^/outpost/outposts$",
+        async () => {
+            await import("@goauthentik/admin/outposts/OutpostListPage");
+            return html`<ak-outpost-list></ak-outpost-list>`;
+        },
+    ],
+    [
+        "^/outpost/integrations$",
+        async () => {
+            await import("@goauthentik/admin/outposts/ServiceConnectionListPage");
+            return html`<ak-outpost-service-connection-list></ak-outpost-service-connection-list>`;
+        },
+    ],
+    [
+        "^/crypto/certificates$",
+        async () => {
+            await import("@goauthentik/admin/crypto/CertificateKeyPairListPage");
+            return html`<ak-crypto-certificate-list></ak-crypto-certificate-list>`;
+        },
+    ],
+    [
+        "^/admin/settings$",
+        async () => {
+            await import("@goauthentik/admin/admin-settings/AdminSettingsPage");
+            return html`<ak-admin-settings></ak-admin-settings>`;
+        },
+    ],
+    [
+        "^/blueprints/instances$",
+        async () => {
+            await import("@goauthentik/admin/blueprints/BlueprintListPage");
+            return html`<ak-blueprint-list></ak-blueprint-list>`;
+        },
+    ],
+    [
+        "^/debug$",
+        async () => {
+            await import("@goauthentik/admin/DebugPage");
+            return html`<ak-admin-debug-page></ak-admin-debug-page>`;
+        },
+    ],
+    [
+        "^/enterprise/licenses$",
+        async () => {
+            await import("@goauthentik/admin/enterprise/EnterpriseLicenseListPage");
+            return html`<ak-enterprise-license-list></ak-enterprise-license-list>`;
+        },
+    ],
 ];
+
+export const ROUTES = _ROUTES.map(makeRoute);
diff --git a/web/src/elements/router/routeUtils.ts b/web/src/elements/router/routeUtils.ts
new file mode 100644
index 0000000000..702a3713f1
--- /dev/null
+++ b/web/src/elements/router/routeUtils.ts
@@ -0,0 +1,37 @@
+import { Route, RouteArgs } from "@goauthentik/elements/router/Route";
+import { P, match } from "ts-pattern";
+
+import { TemplateResult } from "lit";
+
+type RouteInvoke =
+    | ((_1: RouteArgs) => Promise<TemplateResult<1>>)
+    | (() => Promise<TemplateResult<1>>);
+
+type _RawRedirect = [string, string | [string, boolean]];
+type _RawRoute = [string, RouteInvoke];
+export type RawRoute = _RawRoute | _RawRedirect;
+
+// eslint-disable-next-line @typescript-eslint/no-explicit-any
+const isLoader = (v: any): v is RouteInvoke => typeof v === "function";
+
+// When discriminating between redirects and loaders, the loader type is irrelevant to routing
+// correctly. The loader type *is* still well-typed to prevent an incompatible loader being added to
+// a route, but the two different loader types-- ones that take arguments, and ones that do not-- do
+// not matter to the route builder.
+
+// On the other hand, the two different kinds of redirects *do* matter, but only because JavaScript
+// makes a distinction between methods of one argument that can be `call`'ed and methods of more
+// than one argument that must be `apply`'d. (Spread arguments are converted to call or apply as
+// needed).
+
+// prettier-ignore
+export function makeRoute(route: RawRoute): Route {
+    return match(route)
+        .with([P.string, P.when(isLoader)],
+              ([path, loader]) => new Route(new RegExp(path), loader))
+        .with([P.string, P.string],
+              ([path, redirect]) => new Route(new RegExp(path)).redirect(redirect))
+        .with([P.string, [P.string, P.boolean]],
+              ([path, redirect]) => new Route(new RegExp(path)).redirect(...redirect))
+        .exhaustive();
+}
diff --git a/web/src/user/Routes.ts b/web/src/user/Routes.ts
index 72738e1821..e74561f1a5 100644
--- a/web/src/user/Routes.ts
+++ b/web/src/user/Routes.ts
@@ -1,15 +1,20 @@
-import { Route } from "@goauthentik/elements/router/Route";
+import { RawRoute, makeRoute } from "@goauthentik/elements/router/routeUtils";
 import "@goauthentik/user/LibraryPage/LibraryPage";
 
 import { html } from "lit";
 
-export const ROUTES: Route[] = [
+export const _ROUTES: RawRoute[] = [
     // Prevent infinite Shell loops
-    new Route(new RegExp("^/$")).redirect("/library"),
-    new Route(new RegExp("^#.*")).redirect("/library"),
-    new Route(new RegExp("^/library$"), async () => html`<ak-library></ak-library>`),
-    new Route(new RegExp("^/settings$"), async () => {
-        await import("@goauthentik/user/user-settings/UserSettingsPage");
-        return html`<ak-user-settings></ak-user-settings>`;
-    }),
+    ["^/$", "/library"],
+    ["^#.*", "/library"],
+    ["^/library$", async () => html`<ak-library></ak-library>`],
+    [
+        "^/settings$",
+        async () => {
+            await import("@goauthentik/user/user-settings/UserSettingsPage");
+            return html`<ak-user-settings></ak-user-settings>`;
+        },
+    ],
 ];
+
+export const ROUTES = _ROUTES.map(makeRoute);