diff --git a/ui/src/pages/CloudUpstream.test.tsx b/ui/src/pages/CloudUpstream.test.tsx
index 21f4a29464c..4eaee06876e 100644
--- a/ui/src/pages/CloudUpstream.test.tsx
+++ b/ui/src/pages/CloudUpstream.test.tsx
@@ -38,7 +38,7 @@ vi.mock("@/context/BreadcrumbContext", () => ({
 
 vi.mock("@/context/CompanyContext", () => ({
   useCompany: () => ({
-    selectedCompany: { id: "company-1", name: "Paperclip" },
+    selectedCompany: { id: "company-1", name: "Paperclip", issuePrefix: "PAP" },
     selectedCompanyId: "company-1",
   }),
 }));
@@ -136,6 +136,54 @@ describe("CloudUpstream", () => {
     });
   });
 
+  it("sends a company-prefixed redirectUri when starting Connect", async () => {
+    mockCloudUpstreamsApi.list.mockResolvedValue({ connections: [], runs: [] });
+    mockCloudUpstreamsApi.startConnect.mockResolvedValue({
+      pendingConnectionId: "pending-1",
+      authorizationUrl: "https://cloud.example/upstream-consent?state=abc",
+    });
+    const root = createRoot(container);
+    const queryClient = new QueryClient({ defaultOptions: { queries: { retry: false } } });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <CloudUpstream />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+    await flushReact();
+
+    const input = container.querySelector<HTMLInputElement>("input[aria-label='Paperclip Cloud stack URL']");
+    expect(input).toBeTruthy();
+    await act(async () => {
+      const setter = Object.getOwnPropertyDescriptor(HTMLInputElement.prototype, "value")!.set!;
+      setter.call(input!, "https://cloud.example/PAP/dashboard");
+      input!.dispatchEvent(new Event("input", { bubbles: true }));
+    });
+    await flushReact();
+
+    const connectButton = Array.from(container.querySelectorAll("button"))
+      .find((button) => button.textContent?.trim() === "Connect") as HTMLButtonElement | undefined;
+    expect(connectButton).toBeTruthy();
+
+    await act(async () => {
+      connectButton?.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+    });
+    await flushReact();
+
+    expect(mockCloudUpstreamsApi.startConnect).toHaveBeenCalledWith({
+      companyId: "company-1",
+      remoteUrl: "https://cloud.example/PAP/dashboard",
+      redirectUri: `${window.location.origin}/PAP/company/settings/cloud-upstream`,
+    });
+
+    await act(async () => {
+      root.unmount();
+    });
+  });
+
   it("keeps retry only for failed or cancelled runs", async () => {
     mockCloudUpstreamsApi.list.mockResolvedValue(stateWithRun(buildRun({ status: "failed" })));
     const root = createRoot(container);
diff --git a/ui/src/pages/CloudUpstream.tsx b/ui/src/pages/CloudUpstream.tsx
index b99f4e80840..fe3735cf478 100644
--- a/ui/src/pages/CloudUpstream.tsx
+++ b/ui/src/pages/CloudUpstream.tsx
@@ -24,6 +24,7 @@ import { cloudUpstreamsApi } from "@/api/cloudUpstreams";
 import { instanceSettingsApi } from "@/api/instanceSettings";
 import { useBreadcrumbs } from "@/context/BreadcrumbContext";
 import { useCompany } from "@/context/CompanyContext";
+import { applyCompanyPrefix } from "@/lib/company-routes";
 import { Link, useLocation } from "@/lib/router";
 import { queryKeys } from "@/lib/queryKeys";
 
@@ -101,6 +102,8 @@ export function CloudUpstream() {
   const state = callbackParams.get("state");
   const callbackError = callbackParams.get("error");
 
+  const settingsPath = applyCompanyPrefix("/company/settings/cloud-upstream", selectedCompany?.issuePrefix ?? null);
+
   const finishMutation = useMutation({
     mutationFn: (input: { pendingConnectionId: string; code: string; state: string }) =>
       cloudUpstreamsApi.finishConnect(input),
@@ -109,7 +112,7 @@ export function CloudUpstream() {
       setNotice("Cloud upstream connection approved.");
       setActionError(null);
       await invalidateUpstreams();
-      window.history.replaceState(null, "", "/company/settings/cloud-upstream");
+      window.history.replaceState(null, "", settingsPath);
     },
     onError: (error) => setActionError(error instanceof Error ? error.message : "Failed to finish connection."),
   });
@@ -135,7 +138,7 @@ export function CloudUpstream() {
       cloudUpstreamsApi.startConnect({
         companyId: selectedCompanyId!,
         remoteUrl,
-        redirectUri: `${window.location.origin}/company/settings/cloud-upstream`,
+        redirectUri: `${window.location.origin}${settingsPath}`,
       }),
     onSuccess: (result) => {
       localStorage.setItem(PENDING_CONNECTION_KEY, result.pendingConnectionId);