diff --git a/desktop/flipper-server-core/src/utils/runHealthchecks.tsx b/desktop/flipper-server-core/src/utils/runHealthchecks.tsx
index 945fe9c69..8005e516f 100644
--- a/desktop/flipper-server-core/src/utils/runHealthchecks.tsx
+++ b/desktop/flipper-server-core/src/utils/runHealthchecks.tsx
@@ -42,6 +42,8 @@ export async function getHealthChecks(
   });
 }
 
+let envInfoPromise: Promise<FlipperDoctor.EnvironmentInfo> | undefined;
+
 export async function runHealthcheck(
   options: FlipperDoctor.HealthcheckSettings,
   categoryName: keyof FlipperDoctor.Healthchecks,
@@ -60,7 +62,10 @@ export async function runHealthcheck(
     throw new Error('Unknown healthcheck: ' + ruleName);
   }
 
-  const environmentInfo = await getEnvInfo();
+  if (!envInfoPromise) {
+    envInfoPromise = getEnvInfo();
+  }
+  const environmentInfo = await envInfoPromise;
   const checkResult = await check.run!(environmentInfo, options.settings);
   return checkResult.hasProblem && check.isRequired
     ? {
diff --git a/desktop/flipper-ui-browser/src/flipperServerConnection.tsx b/desktop/flipper-ui-browser/src/flipperServerConnection.tsx
index 0185c7ffc..3d57ae928 100644
--- a/desktop/flipper-ui-browser/src/flipperServerConnection.tsx
+++ b/desktop/flipper-ui-browser/src/flipperServerConnection.tsx
@@ -12,7 +12,7 @@ import {FlipperServer} from 'flipper-common';
 import {io, Socket} from 'socket.io-client';
 
 const CONNECTION_TIMEOUT = 30 * 1000;
-const EXEC_TIMOUT = 30 * 10 * 1000;
+const EXEC_TIMOUT = 30 * 1000;
 
 export function createFlipperServer(): Promise<FlipperServer> {
   // TODO: polish this all!
@@ -54,6 +54,10 @@ export function createFlipperServer(): Promise<FlipperServer> {
       window?.flipperShowError?.('WebSocket connection lost');
       console.warn('Socket to Flipper server disconnected');
       connected = false;
+      pendingRequests.forEach((r) =>
+        r.reject(new Error('FLIPPER_SERVER_SOCKET_CONNECT_LOST')),
+      );
+      pendingRequests.clear();
     });
 
     socket.on('exec-response', (id: number, data: any) => {
diff --git a/desktop/flipper-ui-core/src/dispatcher/flipperServer.tsx b/desktop/flipper-ui-core/src/dispatcher/flipperServer.tsx
index f6ecfe0e1..dcd7369c8 100644
--- a/desktop/flipper-ui-core/src/dispatcher/flipperServer.tsx
+++ b/desktop/flipper-ui-core/src/dispatcher/flipperServer.tsx
@@ -59,7 +59,7 @@ export function connectFlipperServerToStore(
             {'' + err}
           </>
         ) : (
-          <>Failed to start Flipper server: ${err.message}</>
+          <>Failed to start Flipper server: {err.message ?? err}</>
         ),
       duration: null,
     });
diff --git a/desktop/flipper-ui-core/src/utils/runHealthchecks.tsx b/desktop/flipper-ui-core/src/utils/runHealthchecks.tsx
index 34b3f9420..c5aa483f2 100644
--- a/desktop/flipper-ui-core/src/utils/runHealthchecks.tsx
+++ b/desktop/flipper-ui-core/src/utils/runHealthchecks.tsx
@@ -50,12 +50,21 @@ async function launchHealthchecks(options: HealthcheckOptions): Promise<void> {
       continue;
     }
     for (const h of category.healthchecks) {
-      const checkResult = await flipperServer.exec(
-        'doctor-run-healthcheck',
-        {settings: options.settings},
-        categoryKey as keyof FlipperDoctor.Healthchecks,
-        h.key,
-      );
+      const checkResult: FlipperDoctor.HealthcheckResult = await flipperServer
+        .exec(
+          'doctor-run-healthcheck',
+          {settings: options.settings},
+          categoryKey as keyof FlipperDoctor.Healthchecks,
+          h.key,
+        )
+        .catch((e) => {
+          console.error('Failed to run doctor check', e);
+          return {
+            status: 'FAILED',
+            isAcknowledged: false,
+            message: 'Failed to run doctor check: ' + e,
+          };
+        });
       const metricName = `doctor:${h.key.replace('.', ':')}.healthcheck`; // e.g. "doctor:ios:xcode-select.healthcheck"
       if (checkResult.status !== 'SUCCESS') {
         hasProblems = true;