diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index f04c976..4ebfd58 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -9,7 +9,7 @@ on:
 
 jobs:
   # Matrix test for all supported platforms and architectures
-  
+
   integration-tests:
     name: ${{ matrix.os }} (${{ matrix.arch }}) tailscale-${{ matrix.version }}
     strategy:
@@ -34,13 +34,13 @@ jobs:
             runner-os: Linux
             arch: amd64
             version: 1.82.0
-          
+
           # Linux tests (ARM64)
           - os: ubuntu-24.04-arm
             runner-os: Linux
             arch: arm64
             version: latest
-          
+
           # Windows tests (AMD64)
           - os: windows-latest
             runner-os: Windows
@@ -52,46 +52,46 @@ jobs:
             runner-os: Windows
             arch: amd64
             version: unstable
-          
+
           # Windows tests (ARM64)
           - os: windows-11-arm
             runner-os: Windows
             arch: arm64
             version: latest
-            
+
           # macOS intel
           - os: macos-13
             runner-os: macOS
             arch: amd64
             version: latest
             ping: 100.99.0.2 # hostnames aren't resolving on MacOS, just ping IP lax-pve.pineapplefish.ts.net,lax-pve
-          
+
           # macOS ARM
           - os: macos-14
             runner-os: macOS
             arch: arm64
             version: latest
-    
+
     runs-on: ${{ matrix.os }}
-    
+
     steps:
       - name: Checkout
         uses: actions/checkout@v4
-      
+
       - name: Setup Node.js
         uses: actions/setup-node@v4
         with:
-          node-version: '20'
-          cache: 'npm'
-      
+          node-version: "20"
+          cache: "npm"
+
       - name: Install Dependencies
         run: npm ci
-      
+
       - name: Build Action
         run: npm run build
-      
+
       # Test with OAuth authentication
-      - name: Test Tailscale Setup (OAuth)
+      - name: Test Action
         id: tailscale-oauth
         uses: ./
         with:
@@ -103,7 +103,7 @@ jobs:
           timeout: "5m"
           retry: 3
           ping: "${{ matrix.ping }}"
-      
+
       # Test Tailscale status command
       - name: Check Tailscale Status
         if: steps.tailscale-oauth.outcome == 'success'
@@ -119,4 +119,3 @@ jobs:
             tailscale version
           fi
         shell: bash
-      
\ No newline at end of file
diff --git a/dist/index.js b/dist/index.js
index a8643f7..5855a44 100644
--- a/dist/index.js
+++ b/dist/index.js
@@ -41123,6 +41123,7 @@ const fs = __importStar(__nccwpck_require__(79896));
 const http = __importStar(__nccwpck_require__(58611));
 const os = __importStar(__nccwpck_require__(70857));
 const path = __importStar(__nccwpck_require__(16928));
+const promises_1 = __nccwpck_require__(16460);
 const cmdTailscale = "tailscale";
 const cmdTailscaleFullPath = "/usr/local/bin/tailscale";
 const cmdTailscaled = "tailscaled";
@@ -41241,7 +41242,7 @@ async function run() {
             core.debug(`Tailscale status: ${JSON.stringify(status)}`);
             if (status.BackendState === "Running") {
                 core.info("✅ Tailscale is running and connected!");
-                pingHostsIfNecessary(config);
+                await pingHostsIfNecessary(config);
                 // Explicitly exit to prevent hanging
                 process.exit(0);
             }
@@ -41254,7 +41255,7 @@ async function run() {
             core.warning(`Failed to get Tailscale status: ${err}`);
             // Still exit successfully since the main connection worked
             core.info("✅ Tailscale daemon is connected!");
-            pingHostsIfNecessary(config);
+            await pingHostsIfNecessary(config);
             // Explicitly exit to prevent hanging
             process.exit(0);
         }
@@ -41264,31 +41265,33 @@ async function run() {
     }
 }
 async function pingHostsIfNecessary(config) {
-    const directConnectionWarning = "direct connection not established";
     if (config.pingHosts.length == 0) {
         return;
     }
-    core.info(`Will ping hosts ${config.pingHosts.join(",")} up to 3 minutes in order to check connectivity`);
+    core.info(`Will ping hosts ${config.pingHosts.join(",")} up to 3 minutes each in order to check connectivity`);
     for (const host of config.pingHosts) {
-        core.info(`Pinging host ${host}`);
-        let result = await exec.getExecOutput(cmdTailscale, [
-            "ping",
-            "-c",
-            "36",
-            host,
-        ]);
+        await pingHost(host);
+    }
+}
+async function pingHost(host) {
+    core.info(`Pinging host ${host}`);
+    for (let i = 0; i <= 36; i++) {
+        if (i < 0) {
+            // wait 5 seconds before pinging
+            (0, promises_1.setTimeout)(5000);
+        }
+        let result = await exec.getExecOutput(cmdTailscale, ["ping", "-c", "1", host], { ignoreReturnCode: true });
         if (result.exitCode === 0) {
-            core.info(`✅ Ping host ${host} responded!`);
+            core.info(`✅ Ping host ${host} reachable via direct connection!`);
+            return;
         }
-        else if (result.stderr.includes(directConnectionWarning) ||
-            result.stdout.includes(directConnectionWarning)) {
-            core.warning(`⚠️ Ping host ${host} reachable only via DERP, not direct connection.`);
-        }
-        else {
-            core.setFailed(`❌ Ping host ${host} did not respond`);
-            process.exit(1);
+        else if (result.stderr.includes("direct connection not established")) {
+            core.info(`✅ Ping host ${host} reachable via DERP!`);
+            return;
         }
     }
+    core.setFailed(`❌ Ping host ${host} did not respond`);
+    process.exit(1);
 }
 async function getInputs() {
     let ping = core.getInput("ping");
@@ -42006,6 +42009,14 @@ module.exports = require("timers");
 
 /***/ }),
 
+/***/ 16460:
+/***/ ((module) => {
+
+"use strict";
+module.exports = require("timers/promises");
+
+/***/ }),
+
 /***/ 64756:
 /***/ ((module) => {
 
diff --git a/src/main.ts b/src/main.ts
index 72a174c..f643183 100644
--- a/src/main.ts
+++ b/src/main.ts
@@ -8,6 +8,7 @@ import * as fs from "fs";
 import * as http from "http";
 import * as os from "os";
 import * as path from "path";
+import { setTimeout as wait } from "timers/promises";
 
 const cmdTailscale = "tailscale";
 const cmdTailscaleFullPath = "/usr/local/bin/tailscale";
@@ -167,7 +168,7 @@ async function run(): Promise<void> {
       core.debug(`Tailscale status: ${JSON.stringify(status)}`);
       if (status.BackendState === "Running") {
         core.info("✅ Tailscale is running and connected!");
-        pingHostsIfNecessary(config);
+        await pingHostsIfNecessary(config);
         // Explicitly exit to prevent hanging
         process.exit(0);
       } else {
@@ -178,7 +179,7 @@ async function run(): Promise<void> {
       core.warning(`Failed to get Tailscale status: ${err}`);
       // Still exit successfully since the main connection worked
       core.info("✅ Tailscale daemon is connected!");
-      pingHostsIfNecessary(config);
+      await pingHostsIfNecessary(config);
       // Explicitly exit to prevent hanging
       process.exit(0);
     }
@@ -188,8 +189,6 @@ async function run(): Promise<void> {
 }
 
 async function pingHostsIfNecessary(config: TailscaleConfig): Promise<void> {
-  const directConnectionWarning = "direct connection not established";
-
   if (config.pingHosts.length == 0) {
     return;
   }
@@ -197,30 +196,35 @@ async function pingHostsIfNecessary(config: TailscaleConfig): Promise<void> {
   core.info(
     `Will ping hosts ${config.pingHosts.join(
       ","
-    )} up to 3 minutes in order to check connectivity`
+    )} up to 3 minutes each in order to check connectivity`
   );
   for (const host of config.pingHosts) {
-    core.info(`Pinging host ${host}`);
-    let result = await exec.getExecOutput(cmdTailscale, [
-      "ping",
-      "-c",
-      "36",
-      host,
-    ]);
+    await pingHost(host);
+  }
+}
+
+async function pingHost(host: string): Promise<void> {
+  core.info(`Pinging host ${host}`);
+  for (let i = 0; i <= 36; i++) {
+    if (i < 0) {
+      // wait 5 seconds before pinging
+      wait(5000);
+    }
+    let result = await exec.getExecOutput(
+      cmdTailscale,
+      ["ping", "-c", "1", host],
+      { ignoreReturnCode: true }
+    );
     if (result.exitCode === 0) {
-      core.info(`✅ Ping host ${host} responded!`);
-    } else if (
-      result.stderr.includes(directConnectionWarning) ||
-      result.stdout.includes(directConnectionWarning)
-    ) {
-      core.warning(
-        `⚠️ Ping host ${host} reachable only via DERP, not direct connection.`
-      );
-    } else {
-      core.setFailed(`❌ Ping host ${host} did not respond`);
-      process.exit(1);
+      core.info(`✅ Ping host ${host} reachable via direct connection!`);
+      return;
+    } else if (result.stderr.includes("direct connection not established")) {
+      core.info(`✅ Ping host ${host} reachable via DERP!`);
+      return;
     }
   }
+  core.setFailed(`❌ Ping host ${host} did not respond`);
+  process.exit(1);
 }
 
 async function getInputs(): Promise<TailscaleConfig> {