diff --git a/packages/core/src/awsService/ec2/model.ts b/packages/core/src/awsService/ec2/model.ts
index 9a5e13feaef..4817d012b8a 100644
--- a/packages/core/src/awsService/ec2/model.ts
+++ b/packages/core/src/awsService/ec2/model.ts
@@ -29,7 +29,7 @@ import {
     testSshConnection,
 } from '../../shared/extensions/ssh'
 import { getLogger } from '../../shared/logger/logger'
-import { CancellationError, Timeout } from '../../shared/utilities/timeoutUtils'
+import { CancellationError, Timeout, waitUntil } from '../../shared/utilities/timeoutUtils'
 import { showMessageWithCancel } from '../../shared/utilities/messages'
 import { SshConfig } from '../../shared/sshConfig'
 import { SshKeyPair } from './sshKeyPair'
@@ -150,8 +150,14 @@ export class Ec2Connecter implements vscode.Disposable {
         }
     }
 
-    private async checkForInstanceSsmError(selection: Ec2Selection): Promise<void> {
-        const isSsmAgentRunning = (await this.ssmClient.getInstanceAgentPingStatus(selection.instanceId)) === 'Online'
+    public async checkForInstanceSsmError(
+        selection: Ec2Selection,
+        options?: Partial<{ interval: number; timeout: number }>
+    ): Promise<void> {
+        const isSsmAgentRunning = await waitUntil(
+            async () => (await this.ssmClient.getInstanceAgentPingStatus(selection.instanceId)) === 'Online',
+            { interval: options?.interval ?? 500, timeout: options?.timeout ?? 5000 }
+        )
 
         if (!isSsmAgentRunning) {
             this.throwConnectionError('Is SSM Agent running on the target instance?', selection, {
diff --git a/packages/core/src/test/awsService/ec2/model.test.ts b/packages/core/src/test/awsService/ec2/model.test.ts
index e113332a60d..998726680d6 100644
--- a/packages/core/src/test/awsService/ec2/model.test.ts
+++ b/packages/core/src/test/awsService/ec2/model.test.ts
@@ -125,6 +125,17 @@ describe('Ec2ConnectClient', function () {
             }
         })
 
+        it('retries if agent status is not online', async function () {
+            const instanceAgentStatus = sinon.stub(SsmClient.prototype, 'getInstanceAgentPingStatus')
+            instanceAgentStatus.onFirstCall().resolves('Offline')
+            instanceAgentStatus.onSecondCall().resolves('Online')
+            try {
+                await client.checkForInstanceSsmError(instanceSelection, { interval: 10, timeout: 100 })
+            } catch (err) {
+                assert.ok(false, `checkForInstanceSsmError failed with error '${err}'`)
+            }
+        })
+
         it('does not throw an error if all checks pass', async function () {
             sinon.stub(Ec2Connecter.prototype, 'isInstanceRunning').resolves(true)
             sinon.stub(Ec2Connecter.prototype, 'getAttachedIamRole').resolves({ Arn: 'testRole' } as IAM.Role)