diff --git a/src/main/transports/electron-net.ts b/src/main/transports/electron-net.ts
index 7d30cfc36..bde1efdb3 100644
--- a/src/main/transports/electron-net.ts
+++ b/src/main/transports/electron-net.ts
@@ -42,6 +42,9 @@ function getRequestOptions(url: string): Electron.ClientRequestConstructorOption
     path: `${pathname}${search}`,
     port: parseInt(port, 10),
     protocol,
+    // Use a non-persistent in-memory session to avoid triggering a macOS keychain
+    // prompt during Chromium's cookie-store initialization of the default session.
+    partition: 'sentry-electron',
   };
 }
 
diff --git a/test/e2e/runner.ts b/test/e2e/runner.ts
index c065dd7b8..388ff81ad 100644
--- a/test/e2e/runner.ts
+++ b/test/e2e/runner.ts
@@ -90,11 +90,7 @@ export function electronTestRunner(
 
   let resolve: undefined | (() => void);
   let reject: undefined | ((reason: unknown) => void);
-
-  const completePromise = new Promise<void>((res, rej) => {
-    resolve = res;
-    reject = rej;
-  });
+  let completePromise: Promise<void> = Promise.resolve();
 
   const unorderedEvents: Array<Envelope | MinidumpResult> = [];
 
@@ -110,18 +106,39 @@ export function electronTestRunner(
       unorderedEvents.push(event);
 
       if (unorderedEvents.length === expectations.length) {
-        const expectedEvents = expectations.map((e) => {
-          if ('envelope' in e) {
-            return e.envelope;
-          }
-          if ('minidump' in e) {
-            return e.minidump;
-          }
+        // Match each received event to one expectation. Processed in arrival order so that
+        // function matchers with cross-event side-effects (e.g. capturing a session ID in
+        // the first handler and verifying it in the second) fire in dependency order.
+        const unmatched = [...expectations];
+
+        for (const received of unorderedEvents) {
+          const idx = unmatched.findIndex((expected) => {
+            try {
+              if ('envelope' in expected) {
+                if (typeof expected.envelope === 'function') {
+                  expected.envelope(received as Envelope);
+                } else {
+                  expect(received).toEqual(expected.envelope);
+                }
+              } else if ('minidump' in expected) {
+                if (typeof expected.minidump === 'function') {
+                  expected.minidump(received as MinidumpResult);
+                } else {
+                  expect(received).toEqual(expected.minidump);
+                }
+              }
+              return true;
+            } catch {
+              return false;
+            }
+          });
 
-          return undefined;
-        });
+          if (idx === -1) {
+            throw new Error(`No expectation matched received event:\n${inspect(received, false, null, true)}`);
+          }
 
-        expect(unorderedEvents).toEqual(expect.arrayContaining(expectedEvents));
+          unmatched.splice(idx, 1);
+        }
 
         if (options.waitAfterExpectedEvents) {
           delay(options.waitAfterExpectedEvents).then(() => {
@@ -182,7 +199,13 @@ export function electronTestRunner(
 
   beforeEach(async () => {
     electronPath = await downloadElectron(electronVersion.string);
-    server = createSentryTestServer(logger, ignoreOrder ? onNewServerEventIgnoreOrder : onNewServerEvent);
+    server = createSentryTestServer(logger, (event) => {
+      if (ignoreOrder) {
+        onNewServerEventIgnoreOrder(event);
+      } else {
+        onNewServerEvent(event);
+      }
+    });
 
     await prepareTestFiles(logger, testPath, testExecutionRoot, electronVersion.string, server.port, convertToEsm);
     await installDepsAndBuild(logger, options.packageManager || 'yarn', testExecutionRoot, hasBuildScript);
@@ -202,6 +225,17 @@ export function electronTestRunner(
   });
 
   test(description, { timeout: options.timeout || 15_000 }, async () => {
+    // Reset state for retries
+    expectations.length = 0;
+    unorderedEvents.length = 0;
+    expectedErrorOutput = undefined;
+    ignoreOrder = false;
+    includeSessionEnvelopes = false;
+    completePromise = new Promise<void>((res, rej) => {
+      resolve = res;
+      reject = rej;
+    });
+
     if (!electronPath) {
       throw new Error('Electron path is not set');
     }
diff --git a/test/e2e/test-apps/other/browser-profiling-trace/test.ts b/test/e2e/test-apps/other/browser-profiling-trace/test.ts
index e75c3bb0f..bfc414615 100644
--- a/test/e2e/test-apps/other/browser-profiling-trace/test.ts
+++ b/test/e2e/test-apps/other/browser-profiling-trace/test.ts
@@ -9,6 +9,7 @@ import {
 
 electronTestRunner(__dirname, async (ctx) => {
   await ctx
+    .ignoreExpectationOrder()
     // Expect the transaction with profile context (trace mode automatically profiles spans)
     .expect({
       envelope: transactionEnvelope({