diff --git a/packages/core/src/awsService/ec2/sshKeyPair.ts b/packages/core/src/awsService/ec2/sshKeyPair.ts
index 1b7a461655d..0bc01b12367 100644
--- a/packages/core/src/awsService/ec2/sshKeyPair.ts
+++ b/packages/core/src/awsService/ec2/sshKeyPair.ts
@@ -8,6 +8,7 @@ import { ToolkitError } from '../../shared/errors'
 import { tryRun } from '../../shared/utilities/pathFind'
 import { Timeout } from '../../shared/utilities/timeoutUtils'
 import { findAsync } from '../../shared/utilities/collectionUtils'
+import { RunParameterContext } from '../../shared/utilities/processUtils'
 
 type sshKeyType = 'rsa' | 'ed25519'
 
@@ -17,7 +18,7 @@ export class SshKeyPair {
     private deleted: boolean = false
 
     private constructor(
-        private keyPath: string,
+        private readonly keyPath: string,
         lifetime: number
     ) {
         this.publicKeyPath = `${keyPath}.pub`
@@ -29,10 +30,6 @@ export class SshKeyPair {
     }
 
     public static async getSshKeyPair(keyPath: string, lifetime: number) {
-        // Overwrite key if already exists
-        if (await fs.existsFile(keyPath)) {
-            await fs.delete(keyPath)
-        }
         await SshKeyPair.generateSshKeyPair(keyPath)
         return new SshKeyPair(keyPath, lifetime)
     }
@@ -50,7 +47,12 @@ export class SshKeyPair {
      * @param keyType type of key to generate.
      */
     public static async tryKeyGen(keyPath: string, keyType: sshKeyType): Promise<boolean> {
-        return !(await tryRun('ssh-keygen', ['-t', keyType, '-N', '', '-q', '-f', keyPath], 'yes', 'unknown key type'))
+        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,
+        }))
     }
 
     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 a61d081c0c4..585dd2cde93 100644
--- a/packages/core/src/shared/utilities/pathFind.ts
+++ b/packages/core/src/shared/utilities/pathFind.ts
@@ -6,7 +6,7 @@
 import * as vscode from 'vscode'
 import * as path from 'path'
 import fs from '../../shared/fs/fs'
-import { ChildProcess } from './processUtils'
+import { ChildProcess, ChildProcessOptions } from './processUtils'
 import { GitExtension } from '../extensions/git'
 import { Settings } from '../settings'
 import { getLogger } from '../logger/logger'
@@ -30,10 +30,11 @@ export async function tryRun(
     p: string,
     args: string[],
     logging: 'yes' | 'no' | 'noresult' = 'yes',
-    expected?: string
+    expected?: string,
+    opt?: ChildProcessOptions
 ): Promise<boolean> {
     const proc = new ChildProcess(p, args, { logging: 'no' })
-    const r = await proc.run()
+    const r = await proc.run(opt)
     const ok = r.exitCode === 0 && (expected === undefined || r.stdout.includes(expected))
     if (logging === 'noresult') {
         getLogger().info('tryRun: %s: %s', ok ? 'ok' : 'failed', proc)
diff --git a/packages/core/src/shared/utilities/processUtils.ts b/packages/core/src/shared/utilities/processUtils.ts
index 7003cc230a7..3e78aa0525c 100644
--- a/packages/core/src/shared/utilities/processUtils.ts
+++ b/packages/core/src/shared/utilities/processUtils.ts
@@ -9,11 +9,13 @@ import * as logger from '../logger'
 import { Timeout, CancellationError, waitUntil } from './timeoutUtils'
 import { isWeb } from '../extensionGlobals'
 
-interface RunParameterContext {
+export interface RunParameterContext {
     /** Reports an error parsed from the stdin/stdout streams. */
     reportError(err: string | Error): void
     /** Attempts to stop the running process. See {@link ChildProcess.stop}. */
     stop(force?: boolean, signal?: string): void
+    /** Send string to stdin */
+    send(text: string): Promise<void>
     /** The active `Timeout` object (if applicable). */
     readonly timeout?: Timeout
     /** The logger being used by the process. */
@@ -161,6 +163,7 @@ export class ChildProcess {
                 timeout,
                 logger: this.#log,
                 stop: this.stop.bind(this),
+                send: this.send.bind(this),
                 reportError: (err) => errorHandler(err instanceof Error ? err : new Error(err)),
             }
 
diff --git a/packages/core/src/test/awsService/ec2/model.test.ts b/packages/core/src/test/awsService/ec2/model.test.ts
index 98c0103c06e..36a7895a35f 100644
--- a/packages/core/src/test/awsService/ec2/model.test.ts
+++ b/packages/core/src/test/awsService/ec2/model.test.ts
@@ -139,8 +139,8 @@ describe('Ec2ConnectClient', function () {
                 instanceId: 'test-id',
                 region: 'test-region',
             }
-            const mockKeys = await SshKeyPair.getSshKeyPair('', 30000)
-            await client.sendSshKeyToInstance(testSelection, mockKeys, '')
+            const mockKeys = await SshKeyPair.getSshKeyPair('fakeDir', 30000)
+            await client.sendSshKeyToInstance(testSelection, mockKeys, 'test-user')
             sinon.assert.calledWith(sendCommandStub, testSelection.instanceId, 'AWS-RunShellScript')
             sinon.restore()
         })
diff --git a/packages/core/src/test/awsService/ec2/sshKeyPair.test.ts b/packages/core/src/test/awsService/ec2/sshKeyPair.test.ts
index d0069cdc5a6..3051aea534e 100644
--- a/packages/core/src/test/awsService/ec2/sshKeyPair.test.ts
+++ b/packages/core/src/test/awsService/ec2/sshKeyPair.test.ts
@@ -33,7 +33,7 @@ describe('SshKeyUtility', async function () {
     })
 
     after(async function () {
-        await keyPair.delete()
+        await fs.delete(temporaryDirectory, { recursive: true, force: true })
         clock.uninstall()
         sinon.restore()
     })
diff --git a/packages/core/src/test/techdebt.test.ts b/packages/core/src/test/techdebt.test.ts
index 4818da88070..d83a8d68c85 100644
--- a/packages/core/src/test/techdebt.test.ts
+++ b/packages/core/src/test/techdebt.test.ts
@@ -53,6 +53,6 @@ describe('tech debt', function () {
         // Monitor telemtry to determine removal or snooze
         // toolkit_showNotification.id = sessionSeparation
         // auth_modifyConnection.action = deleteProfile OR auth_modifyConnection.source contains CodeCatalyst
-        fixByDate('2024-9-30', 'Remove the edge case code from the commit that this test is a part of.')
+        fixByDate('2024-10-30', 'Remove the edge case code from the commit that this test is a part of.')
     })
 })