diff --git a/plugins/amazonq/chat/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/amazonq/workspace/context/ProjectContextProviderTest.kt b/plugins/amazonq/chat/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/amazonq/workspace/context/ProjectContextProviderTest.kt
index 6c6df64d414..abde58fe26e 100644
--- a/plugins/amazonq/chat/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/amazonq/workspace/context/ProjectContextProviderTest.kt
+++ b/plugins/amazonq/chat/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/amazonq/workspace/context/ProjectContextProviderTest.kt
@@ -364,7 +364,7 @@ class ProjectContextProviderTest {
                         .withResponseBody(
                             Body(validQueryInlineResponse)
                         )
-                        .withFixedDelay(51) // 10 sec
+                        .withFixedDelay(101) // 100 ms
                 )
             )
 
diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/model/CodeWhispererModel.kt b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/model/CodeWhispererModel.kt
index c511890260e..91da779ab10 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/model/CodeWhispererModel.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/model/CodeWhispererModel.kt
@@ -15,6 +15,7 @@ import com.intellij.util.concurrency.annotations.RequiresEdt
 import software.amazon.awssdk.services.codewhispererruntime.model.Completion
 import software.amazon.awssdk.services.codewhispererruntime.model.GenerateCompletionsResponse
 import software.aws.toolkits.jetbrains.core.credentials.ToolkitConnection
+import software.aws.toolkits.jetbrains.services.amazonq.SUPPLEMENTAL_CONTEXT_TIMEOUT
 import software.aws.toolkits.jetbrains.services.codewhisperer.codescan.sessionconfig.PayloadContext
 import software.aws.toolkits.jetbrains.services.codewhisperer.language.CodeWhispererProgrammingLanguage
 import software.aws.toolkits.jetbrains.services.codewhisperer.popup.CodeWhispererPopupManagerNew
@@ -73,7 +74,7 @@ data class SupplementalContextInfo(
         }
 
     val isProcessTimeout: Boolean
-        get() = latency > CodeWhispererConstants.SUPPLEMENTAL_CONTEXT_TIMEOUT
+        get() = latency > SUPPLEMENTAL_CONTEXT_TIMEOUT
 
     companion object {
         fun emptyCrossFileContextInfo(targetFileName: String): SupplementalContextInfo = SupplementalContextInfo(
diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererService.kt b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererService.kt
index d5c7d770106..f11c5014028 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererService.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererService.kt
@@ -53,6 +53,7 @@ import software.aws.toolkits.jetbrains.core.coroutines.projectCoroutineScope
 import software.aws.toolkits.jetbrains.core.credentials.ToolkitConnection
 import software.aws.toolkits.jetbrains.core.credentials.ToolkitConnectionManager
 import software.aws.toolkits.jetbrains.core.credentials.pinning.CodeWhispererConnection
+import software.aws.toolkits.jetbrains.services.amazonq.SUPPLEMENTAL_CONTEXT_TIMEOUT
 import software.aws.toolkits.jetbrains.services.codewhisperer.credentials.CodeWhispererClientAdaptor
 import software.aws.toolkits.jetbrains.services.codewhisperer.customization.CodeWhispererModelConfigurator
 import software.aws.toolkits.jetbrains.services.codewhisperer.editor.CodeWhispererEditorManager
@@ -76,7 +77,6 @@ import software.aws.toolkits.jetbrains.services.codewhisperer.telemetry.CodeWhis
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CaretMovement
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeInsightsSettingsFacade
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants
-import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants.SUPPLEMENTAL_CONTEXT_TIMEOUT
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererUtil.getCompletionType
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererUtil.getTelemetryOptOutPreference
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererUtil.notifyErrorCodeWhispererUsageLimit
diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererServiceNew.kt b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererServiceNew.kt
index 2e36bbce349..7f43e3d0882 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererServiceNew.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/service/CodeWhispererServiceNew.kt
@@ -53,6 +53,7 @@ import software.aws.toolkits.jetbrains.core.coroutines.projectCoroutineScope
 import software.aws.toolkits.jetbrains.core.credentials.ToolkitConnection
 import software.aws.toolkits.jetbrains.core.credentials.ToolkitConnectionManager
 import software.aws.toolkits.jetbrains.core.credentials.pinning.CodeWhispererConnection
+import software.aws.toolkits.jetbrains.services.amazonq.SUPPLEMENTAL_CONTEXT_TIMEOUT
 import software.aws.toolkits.jetbrains.services.codewhisperer.credentials.CodeWhispererClientAdaptor
 import software.aws.toolkits.jetbrains.services.codewhisperer.customization.CodeWhispererModelConfigurator
 import software.aws.toolkits.jetbrains.services.codewhisperer.editor.CodeWhispererEditorManagerNew
@@ -78,7 +79,6 @@ import software.aws.toolkits.jetbrains.services.codewhisperer.telemetry.CodeWhis
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CaretMovement
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeInsightsSettingsFacade
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants
-import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants.SUPPLEMENTAL_CONTEXT_TIMEOUT
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererUtil.getCompletionType
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererUtil.getTelemetryOptOutPreference
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererUtil.notifyErrorCodeWhispererUsageLimit
diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/util/CodeWhispererConstants.kt b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/util/CodeWhispererConstants.kt
index 1e11c245b10..eba9ce1641d 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/util/CodeWhispererConstants.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/util/CodeWhispererConstants.kt
@@ -30,7 +30,6 @@ object CodeWhispererConstants {
     const val POPUP_DELAY: Long = 250
     const val POPUP_DELAY_CHECK_INTERVAL: Long = 25
     const val IDLE_TIME_CHECK_INTERVAL: Long = 25
-    const val SUPPLEMENTAL_CONTEXT_TIMEOUT = 50L
     const val SUPPLEMETAL_CONTEXT_BUFFER = 10L
 
     val AWSTemplateKeyWordsRegex = Regex("(AWSTemplateFormatVersion|Resources|AWS::|Description)")
diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codewhisperer/CodeWhispererServiceTest.kt b/plugins/amazonq/codewhisperer/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codewhisperer/CodeWhispererServiceTest.kt
index 4bff4965c3d..1d5646d3869 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codewhisperer/CodeWhispererServiceTest.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/tst/software/aws/toolkits/jetbrains/services/codewhisperer/CodeWhispererServiceTest.kt
@@ -19,6 +19,7 @@ import org.junit.Test
 import org.mockito.kotlin.any
 import org.mockito.kotlin.argumentCaptor
 import org.mockito.kotlin.doReturn
+import org.mockito.kotlin.eq
 import org.mockito.kotlin.mock
 import org.mockito.kotlin.spy
 import org.mockito.kotlin.times
@@ -35,6 +36,7 @@ import software.aws.toolkits.jetbrains.services.codewhisperer.customization.Code
 import software.aws.toolkits.jetbrains.services.codewhisperer.customization.CodeWhispererModelConfigurator
 import software.aws.toolkits.jetbrains.services.codewhisperer.language.CodeWhispererProgrammingLanguage
 import software.aws.toolkits.jetbrains.services.codewhisperer.language.languages.CodeWhispererJava
+import software.aws.toolkits.jetbrains.services.codewhisperer.model.CaretContext
 import software.aws.toolkits.jetbrains.services.codewhisperer.model.CaretPosition
 import software.aws.toolkits.jetbrains.services.codewhisperer.model.Chunk
 import software.aws.toolkits.jetbrains.services.codewhisperer.model.FileContextInfo
@@ -93,6 +95,33 @@ class CodeWhispererServiceTest {
         projectRule.project.replaceService(AwsConnectionManager::class.java, mock(), disposableRule.disposable)
     }
 
+    @Test
+    fun `getRequestContext should use correct fileContext and timeout to fetch supplementalContext`() = runTest {
+        val fileContextProvider = FileContextProvider.getInstance(projectRule.project)
+        val fileContextProviderSpy = spy(fileContextProvider)
+        projectRule.project.replaceService(FileContextProvider::class.java, fileContextProviderSpy, disposableRule.disposable)
+
+        val requestContext = sut.getRequestContext(
+            TriggerTypeInfo(CodewhispererTriggerType.AutoTrigger, CodeWhispererAutomatedTriggerType.Enter()),
+            editor = projectRule.fixture.editor,
+            project = projectRule.project,
+            file,
+            LatencyContext()
+        )
+
+        requestContext.awaitSupplementalContext()
+        val fileContextCaptor = argumentCaptor<FileContextInfo>()
+        verify(fileContextProviderSpy, times(1)).extractSupplementalFileContext(eq(file), fileContextCaptor.capture(), eq(100))
+        assertThat(fileContextCaptor.firstValue).isEqualTo(
+            FileContextInfo(
+                CaretContext(leftFileContext = "", rightFileContext = "public class Main {}", leftContextOnCurrentLine = ""),
+                "main.java",
+                CodeWhispererJava.INSTANCE,
+                "main.java"
+            )
+        )
+    }
+
     @Test
     fun `getRequestContext should have supplementalContext and customizatioArn if they're present`() {
         whenever(customizationConfig.activeCustomization(projectRule.project)).thenReturn(
diff --git a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/Constants.kt b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/Constants.kt
index aba815bdc78..45341767295 100644
--- a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/Constants.kt
+++ b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/Constants.kt
@@ -37,3 +37,5 @@ const val CODE_TRANSFORM_PREREQUISITES =
     "https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#prerequisites"
 
 const val FEATURE_EVALUATION_PRODUCT_NAME = "CodeWhisperer"
+
+const val SUPPLEMENTAL_CONTEXT_TIMEOUT = 100L
diff --git a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/project/ProjectContextProvider.kt b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/project/ProjectContextProvider.kt
index 2a3f4a19e48..c5ea9fb8177 100644
--- a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/project/ProjectContextProvider.kt
+++ b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/project/ProjectContextProvider.kt
@@ -27,6 +27,7 @@ import software.aws.toolkits.core.utils.getLogger
 import software.aws.toolkits.core.utils.info
 import software.aws.toolkits.core.utils.warn
 import software.aws.toolkits.jetbrains.services.amazonq.FeatureDevSessionContext
+import software.aws.toolkits.jetbrains.services.amazonq.SUPPLEMENTAL_CONTEXT_TIMEOUT
 import software.aws.toolkits.jetbrains.services.cwc.controller.chat.telemetry.getStartUrl
 import software.aws.toolkits.jetbrains.settings.CodeWhispererSettings
 import software.aws.toolkits.telemetry.AmazonqTelemetry
@@ -172,7 +173,7 @@ class ProjectContextProvider(val project: Project, private val encoderServer: En
         }
     }
 
-    suspend fun queryInline(query: String, filePath: String): List<InlineBm25Chunk> = withTimeout(50L) {
+    suspend fun queryInline(query: String, filePath: String): List<InlineBm25Chunk> = withTimeout(SUPPLEMENTAL_CONTEXT_TIMEOUT) {
         cs.async {
             val encrypted = encryptRequest(QueryInlineCompletionRequest(query, filePath))
             val r = sendMsgToLsp(LspMessage.QueryInlineCompletion, encrypted)