diff --git a/packages/core/resources/sagemaker_connect b/packages/core/resources/sagemaker_connect
index a1b7c9c0db0..19d0e1984cc 100755
--- a/packages/core/resources/sagemaker_connect
+++ b/packages/core/resources/sagemaker_connect
@@ -9,13 +9,16 @@ _get_ssm_session_info() {
 
     local url_to_get_session_info="http://localhost:${local_endpoint_port}/get_session?connection_identifier=${aws_resource_arn}&credentials_type=${credentials_type}"
 
+    # Generate unique temporary file name to avoid conflicts
+    local temp_file="/tmp/ssm_session_response_$$_$(date +%s%N).json"
+
     # Use curl with --write-out to capture HTTP status
-    response=$(curl -s -w "%{http_code}" -o /tmp/ssm_session_response.json "$url_to_get_session_info")
+    response=$(curl -s -w "%{http_code}" -o "$temp_file" "$url_to_get_session_info")
     http_status="${response: -3}"
-    session_json=$(cat /tmp/ssm_session_response.json)
+    session_json=$(cat "$temp_file")
     
     # Clean up temporary file
-    rm -f /tmp/ssm_session_response.json
+    rm -f "$temp_file"
 
     if [[ "$http_status" -ne 200 ]]; then
         echo "Error: Failed to get SSM session info. HTTP status: $http_status"
@@ -40,16 +43,21 @@ _get_ssm_session_info_async() {
     local url_base="http://localhost:${local_endpoint_port}/get_session_async"
     local url_to_get_session_info="${url_base}?connection_identifier=${aws_resource_arn}&credentials_type=${credentials_type}&request_id=${request_id}"
 
+    # Generate unique temporary file name to avoid conflicts
+    local temp_file="/tmp/ssm_session_response_$$_$(date +%s%N).json"
+
     local max_retries=60
     local retry_interval=5
     local attempt=1
 
     while (( attempt <= max_retries )); do
-        response=$(curl -s -w "%{http_code}" -o /tmp/ssm_session_response.json "$url_to_get_session_info")
+        response=$(curl -s -w "%{http_code}" -o "$temp_file" "$url_to_get_session_info")
         http_status="${response: -3}"
-        session_json=$(cat /tmp/ssm_session_response.json)
+        session_json=$(cat "$temp_file")
 
         if [[ "$http_status" -eq 200 ]]; then
+            # Clean up temporary file on success
+            rm -f "$temp_file"
             export SSM_SESSION_JSON="$session_json"
             return 0
         elif [[ "$http_status" -eq 202 || "$http_status" -eq 204 ]]; then
@@ -59,10 +67,14 @@ _get_ssm_session_info_async() {
         else
             echo "Error: Failed to get SSM session info. HTTP status: $http_status"
             echo "Response: $session_json"
+            # Clean up temporary file on error
+            rm -f "$temp_file"
             exit 1
         fi
     done
 
+    # Clean up temporary file on timeout
+    rm -f "$temp_file"
     echo "Error: Timed out after $max_retries attempts waiting for session to be ready."
     exit 1
 }
diff --git a/packages/core/src/awsService/sagemaker/detached-server/routes/getSessionAsync.ts b/packages/core/src/awsService/sagemaker/detached-server/routes/getSessionAsync.ts
index e59b1b9dd10..f8dad504067 100644
--- a/packages/core/src/awsService/sagemaker/detached-server/routes/getSessionAsync.ts
+++ b/packages/core/src/awsService/sagemaker/detached-server/routes/getSessionAsync.ts
@@ -50,7 +50,7 @@ export async function handleGetSessionAsync(req: IncomingMessage, res: ServerRes
             const refreshUrl = await store.getRefreshUrl(connectionIdentifier)
             const { spaceName } = parseArn(connectionIdentifier)
 
-            const url = `${refreshUrl}/${encodeURIComponent(spaceName)}?reconnect_identifier=${encodeURIComponent(
+            const url = `${refreshUrl}/${encodeURIComponent(spaceName)}?remote_access_token_refresh=true&reconnect_identifier=${encodeURIComponent(
                 connectionIdentifier
             )}&reconnect_request_id=${encodeURIComponent(requestId)}&reconnect_callback_url=${encodeURIComponent(
                 `http://localhost:${serverInfo.port}/refresh_token`
diff --git a/packages/core/src/awsService/sagemaker/detached-server/utils.ts b/packages/core/src/awsService/sagemaker/detached-server/utils.ts
index 9ac6b6b0303..de01041d4ad 100644
--- a/packages/core/src/awsService/sagemaker/detached-server/utils.ts
+++ b/packages/core/src/awsService/sagemaker/detached-server/utils.ts
@@ -18,6 +18,10 @@ export { open }
 export const mappingFilePath = join(os.homedir(), '.aws', '.sagemaker-space-profiles')
 const tempFilePath = `${mappingFilePath}.tmp`
 
+// Simple file lock to prevent concurrent writes
+let isWriting = false
+const writeQueue: Array<() => Promise<void>> = []
+
 /**
  * Reads the local endpoint info file (default or via env) and returns pid & port.
  * @throws Error if the file is missing, invalid JSON, or missing fields
@@ -100,14 +104,48 @@ export async function readMapping() {
 }
 
 /**
- * Writes the mapping to a temp file and atomically renames it to the target path.
+ * Processes the write queue to ensure only one write operation happens at a time.
  */
-export async function writeMapping(mapping: SpaceMappings) {
+async function processWriteQueue() {
+    if (isWriting || writeQueue.length === 0) {
+        return
+    }
+
+    isWriting = true
     try {
-        const json = JSON.stringify(mapping, undefined, 2)
-        await fs.writeFile(tempFilePath, json)
-        await fs.rename(tempFilePath, mappingFilePath)
-    } catch (err) {
-        throw new Error(`Failed to write mapping file: ${err instanceof Error ? err.message : String(err)}`)
+        while (writeQueue.length > 0) {
+            const writeOperation = writeQueue.shift()!
+            await writeOperation()
+        }
+    } finally {
+        isWriting = false
     }
 }
+
+/**
+ * Writes the mapping to a temp file and atomically renames it to the target path.
+ * Uses a queue to prevent race conditions when multiple requests try to write simultaneously.
+ */
+export async function writeMapping(mapping: SpaceMappings) {
+    return new Promise<void>((resolve, reject) => {
+        const writeOperation = async () => {
+            try {
+                // Generate unique temp file name to avoid conflicts
+                const uniqueTempPath = `${tempFilePath}.${process.pid}.${Date.now()}`
+
+                const json = JSON.stringify(mapping, undefined, 2)
+                await fs.writeFile(uniqueTempPath, json)
+                await fs.rename(uniqueTempPath, mappingFilePath)
+                resolve()
+            } catch (err) {
+                reject(new Error(`Failed to write mapping file: ${err instanceof Error ? err.message : String(err)}`))
+            }
+        }
+
+        writeQueue.push(writeOperation)
+
+        // ProcessWriteQueue handles its own errors via individual operation callbacks
+        // eslint-disable-next-line @typescript-eslint/no-floating-promises
+        processWriteQueue()
+    })
+}
diff --git a/packages/core/src/test/awsService/sagemaker/detached-server/utils.test.ts b/packages/core/src/test/awsService/sagemaker/detached-server/utils.test.ts
index 1eeb5708d11..bc8d0a8867b 100644
--- a/packages/core/src/test/awsService/sagemaker/detached-server/utils.test.ts
+++ b/packages/core/src/test/awsService/sagemaker/detached-server/utils.test.ts
@@ -3,8 +3,13 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
+/* eslint-disable no-restricted-imports */
 import * as assert from 'assert'
-import { parseArn } from '../../../../awsService/sagemaker/detached-server/utils'
+import { parseArn, writeMapping, readMapping } from '../../../../awsService/sagemaker/detached-server/utils'
+import { promises as fs } from 'fs'
+import * as path from 'path'
+import * as os from 'os'
+import { SpaceMappings } from '../../../../awsService/sagemaker/types'
 
 describe('parseArn', () => {
     it('parses a standard SageMaker ARN with forward slash', () => {
@@ -37,3 +42,71 @@ describe('parseArn', () => {
         assert.throws(() => parseArn(invalidArn), /Invalid SageMaker ARN format/)
     })
 })
+
+describe('writeMapping', () => {
+    let testDir: string
+
+    beforeEach(async () => {
+        testDir = await fs.mkdtemp(path.join(os.tmpdir(), 'sagemaker-test-'))
+    })
+
+    afterEach(async () => {
+        await fs.rmdir(testDir, { recursive: true })
+    })
+
+    it('handles concurrent writes without race conditions', async () => {
+        const mapping1: SpaceMappings = {
+            localCredential: {
+                'space-1': { type: 'iam', profileName: 'profile1' },
+            },
+        }
+        const mapping2: SpaceMappings = {
+            localCredential: {
+                'space-2': { type: 'iam', profileName: 'profile2' },
+            },
+        }
+        const mapping3: SpaceMappings = {
+            deepLink: {
+                'space-3': {
+                    requests: {
+                        req1: {
+                            sessionId: 'session-456',
+                            url: 'wss://example3.com',
+                            token: 'token-456',
+                        },
+                    },
+                    refreshUrl: 'https://example3.com/refresh',
+                },
+            },
+        }
+
+        const writePromises = [writeMapping(mapping1), writeMapping(mapping2), writeMapping(mapping3)]
+
+        await Promise.all(writePromises)
+
+        const finalContent = await readMapping()
+        const possibleResults = [mapping1, mapping2, mapping3]
+        const isValidResult = possibleResults.some(
+            (expected) => JSON.stringify(finalContent) === JSON.stringify(expected)
+        )
+        assert.strictEqual(isValidResult, true, 'Final content should match one of the written mappings')
+    })
+
+    it('queues multiple writes and processes them sequentially', async () => {
+        const mappings = Array.from({ length: 5 }, (_, i) => ({
+            localCredential: {
+                [`space-${i}`]: { type: 'iam' as const, profileName: `profile-${i}` },
+            },
+        }))
+
+        const writePromises = mappings.map((mapping) => writeMapping(mapping))
+
+        await Promise.all(writePromises)
+
+        const finalContent = await readMapping()
+        assert.strictEqual(typeof finalContent, 'object', 'Final content should be a valid object')
+
+        const isValidResult = mappings.some((mapping) => JSON.stringify(finalContent) === JSON.stringify(mapping))
+        assert.strictEqual(isValidResult, true, 'Final content should match one of the written mappings')
+    })
+})
diff --git a/packages/toolkit/.changes/next-release/Bug Fix-c6e841d7-e0bb-474c-9540-f896746d26d4.json b/packages/toolkit/.changes/next-release/Bug Fix-c6e841d7-e0bb-474c-9540-f896746d26d4.json
new file mode 100644
index 00000000000..18aea78cb6a
--- /dev/null
+++ b/packages/toolkit/.changes/next-release/Bug Fix-c6e841d7-e0bb-474c-9540-f896746d26d4.json	
@@ -0,0 +1,4 @@
+{
+	"type": "Bug Fix",
+	"description": "SageMaker: Resolve race condition when reconnecting from multiple remote windows."
+}