diff --git a/packages/core/src/awsService/ec2/sshKeyPair.ts b/packages/core/src/awsService/ec2/sshKeyPair.ts
index cb67ca39ba1..75e1426bf26 100644
--- a/packages/core/src/awsService/ec2/sshKeyPair.ts
+++ b/packages/core/src/awsService/ec2/sshKeyPair.ts
@@ -79,10 +79,16 @@ export class SshKeyPair {
         const overrideKeys = async (_t: string, proc: RunParameterContext) => {
             await proc.send('yes')
         }
-        return !(await tryRun('ssh-keygen', ['-t', keyType, '-N', '', '-q', '-f', keyPath], 'yes', 'unknown key type', {
-            onStdout: overrideKeys,
-            timeout: new Timeout(5000),
-        }))
+        return await tryRun(
+            'ssh-keygen',
+            ['-t', keyType, '-N', '', '-q', '-f', keyPath],
+            'yes',
+            /^(?!.*Unknown key type).*/i,
+            {
+                onStdout: overrideKeys,
+                timeout: new Timeout(5000),
+            }
+        )
     }
 
     public static async tryKeyTypes(keyPath: string, keyTypes: sshKeyType[]): Promise<boolean> {
diff --git a/packages/core/src/shared/utilities/pathFind.ts b/packages/core/src/shared/utilities/pathFind.ts
index b1097810d3d..04622733a66 100644
--- a/packages/core/src/shared/utilities/pathFind.ts
+++ b/packages/core/src/shared/utilities/pathFind.ts
@@ -11,6 +11,7 @@ import { GitExtension } from '../extensions/git'
 import { Settings } from '../settings'
 import { getLogger } from '../logger/logger'
 import { mergeResolvedShellPath } from '../env/resolveEnv'
+import { matchesPattern } from './textUtilities'
 
 /** Full path to VSCode CLI. */
 let vscPath: string
@@ -32,7 +33,7 @@ export async function tryRun(
     p: string,
     args: string[],
     logging: 'yes' | 'no' | 'noresult' = 'yes',
-    expected?: string,
+    expected?: string | RegExp,
     opt?: ChildProcessOptions
 ): Promise<boolean> {
     const proc = new ChildProcess(p, args, { logging: 'no' })
@@ -40,7 +41,7 @@ export async function tryRun(
         ...opt,
         spawnOptions: { env: await mergeResolvedShellPath(opt?.spawnOptions?.env ?? process.env) },
     })
-    const ok = r.exitCode === 0 && (expected === undefined || r.stdout.includes(expected))
+    const ok = r.exitCode === 0 && (expected === undefined || matchesPattern(r.stdout, expected))
     if (logging === 'noresult') {
         getLogger().info('tryRun: %s: %s', ok ? 'ok' : 'failed', proc)
     } else if (logging !== 'no') {
diff --git a/packages/core/src/shared/utilities/textUtilities.ts b/packages/core/src/shared/utilities/textUtilities.ts
index e5746df0983..53c2e2be32c 100644
--- a/packages/core/src/shared/utilities/textUtilities.ts
+++ b/packages/core/src/shared/utilities/textUtilities.ts
@@ -273,3 +273,10 @@ export function extractFileAndCodeSelectionFromMessage(message: any) {
     const selection = message?.context?.focusAreaContext?.selectionInsideExtendedCodeBlock as vscode.Selection
     return { filePath, selection }
 }
+
+export function matchesPattern(source: string, target: string | RegExp) {
+    if (typeof target === 'string') {
+        return source.includes(target)
+    }
+    return target.test(source)
+}
diff --git a/packages/core/src/test/shared/utilities/pathFind.test.ts b/packages/core/src/test/shared/utilities/pathFind.test.ts
index 335b4a9327b..43ec92cf680 100644
--- a/packages/core/src/test/shared/utilities/pathFind.test.ts
+++ b/packages/core/src/test/shared/utilities/pathFind.test.ts
@@ -42,6 +42,24 @@ describe('pathFind', function () {
         assert.ok(regex.test(vscPath), `expected regex ${regex} to match: "${vscPath}"`)
     })
 
+    describe('tryRun', function () {
+        it('returns true if output matches expected', async function () {
+            const posResult = await tryRun('echo', ['hello'], 'no', 'hello')
+            assert.ok(posResult)
+
+            const negResult = await tryRun('echo', ['hi'], 'no', 'hello')
+            assert.ok(!negResult)
+        })
+
+        it('supports regex on output match', async function () {
+            const posResult = await tryRun('echo', ['hello'], 'no', /hel*o/)
+            assert.ok(posResult)
+
+            const negResult = await tryRun('echo', ['hi'], 'no', /^(?!(hi)).*$/)
+            assert.ok(!negResult)
+        })
+    })
+
     describe('findSshPath', function () {
         let previousPath: string | undefined