diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/codescan/sessionconfig/CodeScanSessionConfig.kt b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/codescan/sessionconfig/CodeScanSessionConfig.kt
index c6cf9205ea..e02a32e278 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/codescan/sessionconfig/CodeScanSessionConfig.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/codescan/sessionconfig/CodeScanSessionConfig.kt
@@ -31,6 +31,7 @@ import software.aws.toolkits.jetbrains.services.codewhisperer.codescan.utils.Ama
 import software.aws.toolkits.jetbrains.services.codewhisperer.language.CodeWhispererProgrammingLanguage
 import software.aws.toolkits.jetbrains.services.codewhisperer.language.languages.CodeWhispererUnknownLanguage
 import software.aws.toolkits.jetbrains.services.codewhisperer.language.programmingLanguage
+import software.aws.toolkits.jetbrains.services.codewhisperer.telemetry.CodeWhispererTelemetryService
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants.CODE_SCAN_CREATE_PAYLOAD_TIMEOUT_IN_SECONDS
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants.CodeAnalysisScope
 import software.aws.toolkits.jetbrains.services.codewhisperer.util.CodeWhispererConstants.DEFAULT_CODE_SCAN_TIMEOUT_IN_SECONDS
@@ -195,6 +196,9 @@ class CodeScanSessionConfig(
         files.forEach { file ->
             try {
                 val relativePath = "${project.name}/${file.relativeTo(projectRoot.toNioPath())}"
+                if (relativePath.contains("../") || relativePath.contains("..\\")) {
+                    CodeWhispererTelemetryService.getInstance().sendInvalidZipEvent(file, projectRoot.toNioPath(), relativePath)
+                }
                 LOG.debug { "Selected file for truncation: $file" }
                 it.putNextEntry(relativePath.toString(), file)
             } catch (e: Exception) {
diff --git a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/telemetry/CodeWhispererTelemetryService.kt b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/telemetry/CodeWhispererTelemetryService.kt
index 5509fa07f0..59d82c3b44 100644
--- a/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/telemetry/CodeWhispererTelemetryService.kt
+++ b/plugins/amazonq/codewhisperer/jetbrains-community/src/software/aws/toolkits/jetbrains/services/codewhisperer/telemetry/CodeWhispererTelemetryService.kt
@@ -51,9 +51,11 @@ import software.aws.toolkits.telemetry.Component
 import software.aws.toolkits.telemetry.CredentialSourceId
 import software.aws.toolkits.telemetry.MetricResult
 import software.aws.toolkits.telemetry.Result
+import java.nio.file.Path
 import java.time.Duration
 import java.time.Instant
 import java.util.Queue
+import kotlin.io.path.pathString
 
 @Service
 class CodeWhispererTelemetryService {
@@ -609,6 +611,14 @@ class CodeWhispererTelemetryService {
         assert(ApplicationManager.getApplication().isUnitTestMode)
         return this.previousUserTriggerDecisions
     }
+
+    fun sendInvalidZipEvent(filePath: Path, projectRoot: Path, relativePath: String) {
+        CodewhispererTelemetry.invalidZip(
+            filePath = filePath.pathString,
+            workspaceRoot = projectRoot.pathString,
+            relativePath = relativePath
+        )
+    }
 }
 
 fun isTelemetryEnabled(): Boolean = AwsSettings.getInstance().isTelemetryEnabled
diff --git a/plugins/core/jetbrains-community/resources/telemetryOverride.json b/plugins/core/jetbrains-community/resources/telemetryOverride.json
index 3acc0cdce1..39e9d4ba31 100644
--- a/plugins/core/jetbrains-community/resources/telemetryOverride.json
+++ b/plugins/core/jetbrains-community/resources/telemetryOverride.json
@@ -177,6 +177,21 @@
                 "reloaded"
             ],
             "description": "Toolkit run state."
+        },
+        {
+            "name": "filePath",
+            "type": "string",
+            "description": "The path of the file"
+        },
+        {
+            "name": "workspaceRoot",
+            "type": "string",
+            "description": "The path of the project root"
+        },
+        {
+            "name": "relativePath",
+            "type": "string",
+            "description": "The relative path of the file"
         }
     ],
     "metrics": [
@@ -530,6 +545,24 @@
                 }
             ],
             "passive": true
+        },
+        {
+            "name": "codewhisperer_invalidZip",
+            "description": "Invalid zip file",
+            "metadata": [
+                {
+                    "type": "filePath",
+                    "required": true
+                },
+                {
+                    "type": "workspaceRoot",
+                    "required": true
+                },
+                {
+                    "type": "relativePath",
+                    "required": true
+                }
+            ]
         }
     ]
 }