diff --git a/cli/src/__tests__/network-bind.test.ts b/cli/src/__tests__/network-bind.test.ts
index d75452ab..513e3853 100644
--- a/cli/src/__tests__/network-bind.test.ts
+++ b/cli/src/__tests__/network-bind.test.ts
@@ -2,6 +2,8 @@ import { describe, expect, it } from "vitest";
 import { resolveRuntimeBind, validateConfiguredBindMode } from "@paperclipai/shared";
 import { buildPresetServerConfig } from "../config/server-bind.js";
 
+const ORIGINAL_PATH = process.env.PATH;
+
 describe("network bind helpers", () => {
   it("rejects non-loopback bind modes in local_trusted", () => {
     expect(
@@ -50,13 +52,18 @@ describe("network bind helpers", () => {
 
   it("falls back to loopback when no tailscale address is available for tailnet presets", () => {
     delete process.env.PAPERCLIP_TAILNET_BIND_HOST;
+    process.env.PATH = "";
 
-    const preset = buildPresetServerConfig("tailnet", {
-      port: 3100,
-      allowedHostnames: [],
-      serveUi: true,
-    });
+    try {
+      const preset = buildPresetServerConfig("tailnet", {
+        port: 3100,
+        allowedHostnames: [],
+        serveUi: true,
+      });
 
-    expect(preset.server.host).toBe("127.0.0.1");
+      expect(preset.server.host).toBe("127.0.0.1");
+    } finally {
+      process.env.PATH = ORIGINAL_PATH;
+    }
   });
 });
diff --git a/cli/src/__tests__/onboard.test.ts b/cli/src/__tests__/onboard.test.ts
index 0c694f4b..b7c01eb5 100644
--- a/cli/src/__tests__/onboard.test.ts
+++ b/cli/src/__tests__/onboard.test.ts
@@ -7,6 +7,7 @@ import type { PaperclipConfig } from "../config/schema.js";
 
 const ORIGINAL_ENV = { ...process.env };
 const ORIGINAL_CWD = process.cwd();
+const ORIGINAL_PATH = process.env.PATH;
 
 function createExistingConfigFixture() {
   const root = fs.mkdtempSync(path.join(os.tmpdir(), "paperclip-onboard-"));
@@ -171,8 +172,13 @@ describe("onboard", () => {
   it("keeps tailnet quickstart on loopback until tailscale is available", async () => {
     const configPath = createFreshConfigPath();
     delete process.env.PAPERCLIP_TAILNET_BIND_HOST;
+    process.env.PATH = "";
 
-    await onboard({ config: configPath, yes: true, invokedByRun: true, bind: "tailnet" });
+    try {
+      await onboard({ config: configPath, yes: true, invokedByRun: true, bind: "tailnet" });
+    } finally {
+      process.env.PATH = ORIGINAL_PATH;
+    }
 
     const raw = JSON.parse(fs.readFileSync(configPath, "utf8")) as PaperclipConfig;
     expect(raw.server.deploymentMode).toBe("authenticated");
diff --git a/server/src/__tests__/companies-service.test.ts b/server/src/__tests__/companies-service.test.ts
new file mode 100644
index 00000000..8977b041
--- /dev/null
+++ b/server/src/__tests__/companies-service.test.ts
@@ -0,0 +1,50 @@
+import { afterAll, afterEach, beforeAll, describe, expect, it } from "vitest";
+import { companies, createDb } from "@paperclipai/db";
+import {
+  getEmbeddedPostgresTestSupport,
+  startEmbeddedPostgresTestDatabase,
+} from "./helpers/embedded-postgres.js";
+import { companyService } from "../services/companies.js";
+
+const embeddedPostgresSupport = await getEmbeddedPostgresTestSupport();
+const describeEmbeddedPostgres = embeddedPostgresSupport.supported ? describe : describe.skip;
+
+if (!embeddedPostgresSupport.supported) {
+  console.warn(
+    `Skipping embedded Postgres company service tests on this host: ${embeddedPostgresSupport.reason ?? "unsupported environment"}`,
+  );
+}
+
+describeEmbeddedPostgres("companyService", () => {
+  let db!: ReturnType<typeof createDb>;
+  let tempDb: Awaited<ReturnType<typeof startEmbeddedPostgresTestDatabase>> | null = null;
+
+  beforeAll(async () => {
+    tempDb = await startEmbeddedPostgresTestDatabase("paperclip-company-service-");
+    db = createDb(tempDb.connectionString);
+  }, 20_000);
+
+  afterEach(async () => {
+    await db.delete(companies);
+  });
+
+  afterAll(async () => {
+    await tempDb?.cleanup();
+  });
+
+  it("retries generated issue prefixes when Drizzle wraps the unique constraint error", async () => {
+    await db.insert(companies).values({
+      name: "Aron Existing",
+      issuePrefix: "ARO",
+    });
+
+    const created = await companyService(db).create({
+      name: "Aron & Sharon",
+    });
+
+    expect(created.issuePrefix).toBe("AROA");
+
+    const rows = await db.select({ issuePrefix: companies.issuePrefix }).from(companies);
+    expect(rows.map((row) => row.issuePrefix).sort()).toEqual(["ARO", "AROA"]);
+  });
+});
diff --git a/server/src/services/companies.ts b/server/src/services/companies.ts
index 8704b986..e69abb9e 100644
--- a/server/src/services/companies.ts
+++ b/server/src/services/companies.ts
@@ -125,16 +125,18 @@ export function companyService(db: Db) {
   }
 
   function isIssuePrefixConflict(error: unknown) {
-    const constraint = typeof error === "object" && error !== null && "constraint" in error
-      ? (error as { constraint?: string }).constraint
-      : typeof error === "object" && error !== null && "constraint_name" in error
-        ? (error as { constraint_name?: string }).constraint_name
-        : undefined;
-    return typeof error === "object"
-      && error !== null
-      && "code" in error
-      && (error as { code?: string }).code === "23505"
-      && constraint === "companies_issue_prefix_idx";
+    const seen = new Set<unknown>();
+    let current = error;
+    while (typeof current === "object" && current !== null && !seen.has(current)) {
+      seen.add(current);
+      const maybe = current as { code?: string; constraint?: string; constraint_name?: string; cause?: unknown };
+      const constraint = maybe.constraint ?? maybe.constraint_name;
+      if (maybe.code === "23505" && constraint === "companies_issue_prefix_idx") {
+        return true;
+      }
+      current = maybe.cause;
+    }
+    return false;
   }
 
   async function createCompanyWithUniquePrefix(data: typeof companies.$inferInsert) {
diff --git a/ui/src/components/InstanceSidebar.test.tsx b/ui/src/components/InstanceSidebar.test.tsx
index 2463116b..e49d940b 100644
--- a/ui/src/components/InstanceSidebar.test.tsx
+++ b/ui/src/components/InstanceSidebar.test.tsx
@@ -223,9 +223,14 @@ describe("InstanceSidebar", () => {
     await flushReact();
     await findPluginLinks(container, 1);
 
-    const topLevelLinks = Array.from(
-      container.querySelectorAll<HTMLAnchorElement>('a[href^="/instance/settings/"]'),
-    );
+    await vi.waitFor(() => {
+      const links = Array.from(
+        container.querySelectorAll<HTMLAnchorElement>('a[href^="/instance/settings/"]'),
+      );
+      expect(links.some((a) => a.getAttribute("href") === "/instance/settings/plugins/linear")).toBe(true);
+    });
+
+    const topLevelLinks = Array.from(container.querySelectorAll<HTMLAnchorElement>('a[href^="/instance/settings/"]'));
     const hrefs = topLevelLinks.map((a) => a.getAttribute("href"));
 
     const pluginsIndex = hrefs.indexOf("/instance/settings/plugins");
@@ -266,6 +271,9 @@ describe("InstanceSidebar", () => {
     queryClient = rendered.queryClient;
     await flushReact();
 
+    await vi.waitFor(() => {
+      expect(mockPluginsApi.list).toHaveBeenCalled();
+    });
     const pluginLinks = Array.from(container.querySelectorAll('a[href^="/instance/settings/plugins/"]'));
     expect(pluginLinks).toHaveLength(0);
   });