diff --git a/packages/amazonq/.changes/next-release/Bug Fix-0d324321-bddd-4f93-80c4-80978930f157.json b/packages/amazonq/.changes/next-release/Bug Fix-0d324321-bddd-4f93-80c4-80978930f157.json
new file mode 100644
index 0000000000..643ff10bb7
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Bug Fix-0d324321-bddd-4f93-80c4-80978930f157.json	
@@ -0,0 +1,4 @@
+{
+	"type": "Bug Fix",
+	"description": "Amazon Q /dev: include telemetry for workspace usage when generating new files"
+}
diff --git a/packages/core/src/amazonqFeatureDev/session/sessionState.ts b/packages/core/src/amazonqFeatureDev/session/sessionState.ts
index 9c914462ab..72650fdb2f 100644
--- a/packages/core/src/amazonqFeatureDev/session/sessionState.ts
+++ b/packages/core/src/amazonqFeatureDev/session/sessionState.ts
@@ -56,7 +56,8 @@ function registerNewFiles(
     fs: VirtualFileSystem,
     newFileContents: NewFileZipContents[],
     uploadId: string,
-    workspaceFolders: CurrentWsFolders
+    workspaceFolders: CurrentWsFolders,
+    conversationId: string
 ): NewFileInfo[] {
     const result: NewFileInfo[] = []
     const workspaceFolderPrefixes = getWorkspaceFoldersByPrefixes(workspaceFolders)
@@ -70,6 +71,11 @@ function registerNewFiles(
             workspaceFolderPrefixes === undefined ? '' : zipFilePath.substring(0, zipFilePath.indexOf(path.sep))
         const folder = workspaceFolderPrefixes === undefined ? workspaceFolders[0] : workspaceFolderPrefixes[prefix]
         if (folder === undefined) {
+            telemetry.amazonq_trackScenarioCountUsage.emit({
+                amazonqConversationId: conversationId,
+                credentialStartUrl: AuthUtil.instance.startUrl,
+                scenarioType: 'wsOrphanedDocuments',
+            })
             getLogger().error(`No workspace folder found for file: ${zipFilePath} and prefix: ${prefix}`)
             continue
         }
@@ -161,7 +167,13 @@ abstract class CodeGenBase {
                 case CodeGenerationStatus.COMPLETE: {
                     const { newFileContents, deletedFiles, references } =
                         await this.config.proxyClient.exportResultArchive(this.conversationId)
-                    const newFileInfo = registerNewFiles(fs, newFileContents, this.uploadId, workspaceFolders)
+                    const newFileInfo = registerNewFiles(
+                        fs,
+                        newFileContents,
+                        this.uploadId,
+                        workspaceFolders,
+                        this.conversationId
+                    )
                     telemetry.setNumberOfFilesGenerated(newFileInfo.length)
 
                     return {
@@ -348,7 +360,13 @@ export class MockCodeGenState implements SessionState {
                 zipFilePath: f.zipFilePath,
                 fileContent: f.fileContent,
             }))
-            this.filePaths = registerNewFiles(action.fs, newFileContents, this.uploadId, this.config.workspaceFolders)
+            this.filePaths = registerNewFiles(
+                action.fs,
+                newFileContents,
+                this.uploadId,
+                this.config.workspaceFolders,
+                this.conversationId
+            )
             this.deletedFiles = [
                 {
                     zipFilePath: 'src/this-file-should-be-deleted.ts',
diff --git a/packages/core/src/shared/telemetry/vscodeTelemetry.json b/packages/core/src/shared/telemetry/vscodeTelemetry.json
index fffeec357b..a4624c5775 100644
--- a/packages/core/src/shared/telemetry/vscodeTelemetry.json
+++ b/packages/core/src/shared/telemetry/vscodeTelemetry.json
@@ -315,6 +315,12 @@
             "name": "totalFiles",
             "type": "int",
             "description": "The total number of files being sent to Amazon Q"
+        },
+        {
+            "name": "scenarioType",
+            "type": "string",
+            "allowedValues": ["wsOrphanedDocuments"],
+            "description": "Scenarios to count in telemetry"
         }
     ],
     "metrics": [
@@ -939,6 +945,25 @@
                 }
             ]
         },
+        {
+            "name": "amazonq_trackScenarioCountUsage",
+            "description": "Count how many times a scenario is reached.",
+            "unit": "Count",
+            "metadata": [
+                {
+                    "type": "amazonqConversationId",
+                    "required": true
+                },
+                {
+                    "type": "credentialStartUrl",
+                    "required": false
+                },
+                {
+                    "type": "scenarioType",
+                    "required": true
+                }
+            ]
+        },
         {
             "name": "amazonq_approachThumbsUp",
             "description": "User clicked on the thumbs up button, to mention that they are satisfied",