diff --git a/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt b/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
index cc883a3b..197c32d1 100644
--- a/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
+++ b/src/main/kotlin/com/coder/gateway/cli/CoderCLIManager.kt
@@ -116,6 +116,7 @@ data class Features(
     val disableAutostart: Boolean = false,
     val reportWorkspaceUsage: Boolean = false,
     val wildcardSSH: Boolean = false,
+    val buildReason: Boolean = false,
 )
 
 /**
@@ -479,13 +480,21 @@ class CoderCLIManager(
      *
      * Throws if the command execution fails.
      */
-    fun startWorkspace(workspaceOwner: String, workspaceName: String): String = exec(
-        "--global-config",
-        coderConfigPath.toString(),
-        "start",
-        "--yes",
-        workspaceOwner + "/" + workspaceName,
-    )
+    fun startWorkspace(workspaceOwner: String, workspaceName: String, feats: Features = features): String {
+        val args = mutableListOf(
+            "--global-config",
+            coderConfigPath.toString(),
+            "start",
+            "--yes",
+            workspaceOwner + "/" + workspaceName
+        )
+
+        if (feats.buildReason) {
+            args.addAll(listOf("--reason", "jetbrains_connection"))
+        }
+
+        return exec(*args.toTypedArray())
+    }
 
     private fun exec(vararg args: String): String {
         val stdout =
@@ -511,6 +520,7 @@ class CoderCLIManager(
                     disableAutostart = version >= SemVer(2, 5, 0),
                     reportWorkspaceUsage = version >= SemVer(2, 13, 0),
                     wildcardSSH = version >= SemVer(2, 19, 0),
+                    buildReason = version >= SemVer(2, 25, 0),
                 )
             }
         }
diff --git a/src/main/kotlin/com/coder/gateway/sdk/CoderRestClient.kt b/src/main/kotlin/com/coder/gateway/sdk/CoderRestClient.kt
index 71c6e1ba..3224f517 100644
--- a/src/main/kotlin/com/coder/gateway/sdk/CoderRestClient.kt
+++ b/src/main/kotlin/com/coder/gateway/sdk/CoderRestClient.kt
@@ -15,6 +15,7 @@ import com.coder.gateway.sdk.v2.models.User
 import com.coder.gateway.sdk.v2.models.Workspace
 import com.coder.gateway.sdk.v2.models.WorkspaceAgent
 import com.coder.gateway.sdk.v2.models.WorkspaceBuild
+import com.coder.gateway.sdk.v2.models.WorkspaceBuildReason
 import com.coder.gateway.sdk.v2.models.WorkspaceResource
 import com.coder.gateway.sdk.v2.models.WorkspaceStatus
 import com.coder.gateway.sdk.v2.models.WorkspaceTransition
@@ -244,7 +245,7 @@ open class CoderRestClient(
      * @throws [APIResponseException].
      */
     fun stopWorkspace(workspace: Workspace): WorkspaceBuild {
-        val buildRequest = CreateWorkspaceBuildRequest(null, WorkspaceTransition.STOP)
+        val buildRequest = CreateWorkspaceBuildRequest(null, WorkspaceTransition.STOP, null)
         val buildResponse = retroRestClient.createWorkspaceBuild(workspace.id, buildRequest).execute()
         if (buildResponse.code() != HttpURLConnection.HTTP_CREATED) {
             throw APIResponseException("stop workspace ${workspace.name}", url, buildResponse)
@@ -265,7 +266,11 @@ open class CoderRestClient(
     fun updateWorkspace(workspace: Workspace): WorkspaceBuild {
         val template = template(workspace.templateID)
         val buildRequest =
-            CreateWorkspaceBuildRequest(template.activeVersionID, WorkspaceTransition.START)
+            CreateWorkspaceBuildRequest(
+                template.activeVersionID,
+                WorkspaceTransition.START,
+                WorkspaceBuildReason.JETBRAINS_CONNECTION
+            )
         val buildResponse = retroRestClient.createWorkspaceBuild(workspace.id, buildRequest).execute()
         if (buildResponse.code() != HttpURLConnection.HTTP_CREATED) {
             throw APIResponseException("update workspace ${workspace.name}", url, buildResponse)
diff --git a/src/main/kotlin/com/coder/gateway/sdk/v2/models/CreateWorkspaceBuildRequest.kt b/src/main/kotlin/com/coder/gateway/sdk/v2/models/CreateWorkspaceBuildRequest.kt
index 5f00ddc4..c00261e2 100644
--- a/src/main/kotlin/com/coder/gateway/sdk/v2/models/CreateWorkspaceBuildRequest.kt
+++ b/src/main/kotlin/com/coder/gateway/sdk/v2/models/CreateWorkspaceBuildRequest.kt
@@ -10,6 +10,8 @@ data class CreateWorkspaceBuildRequest(
     @Json(name = "template_version_id") val templateVersionID: UUID?,
     // Use to start and stop the workspace.
     @Json(name = "transition") val transition: WorkspaceTransition,
+    // Use to set build reason for a workspace.
+    @Json(name = "reason") val reason: WorkspaceBuildReason?,
 ) {
     override fun equals(other: Any?): Boolean {
         if (this === other) return true
@@ -19,6 +21,7 @@ data class CreateWorkspaceBuildRequest(
 
         if (templateVersionID != other.templateVersionID) return false
         if (transition != other.transition) return false
+        if (reason != other.reason) return false
 
         return true
     }
@@ -26,6 +29,7 @@ data class CreateWorkspaceBuildRequest(
     override fun hashCode(): Int {
         var result = templateVersionID?.hashCode() ?: 0
         result = 31 * result + transition.hashCode()
+        result = 31 * result + (reason?.hashCode() ?: 0)
         return result
     }
 }
diff --git a/src/main/kotlin/com/coder/gateway/sdk/v2/models/WorkspaceBuildReason.kt b/src/main/kotlin/com/coder/gateway/sdk/v2/models/WorkspaceBuildReason.kt
new file mode 100644
index 00000000..18d50342
--- /dev/null
+++ b/src/main/kotlin/com/coder/gateway/sdk/v2/models/WorkspaceBuildReason.kt
@@ -0,0 +1,7 @@
+package com.coder.gateway.sdk.v2.models
+
+import com.squareup.moshi.Json
+
+enum class WorkspaceBuildReason {
+    @Json(name = "jetbrains_connection") JETBRAINS_CONNECTION,
+}
\ No newline at end of file
diff --git a/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt b/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
index 5ae754ec..73aae020 100644
--- a/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
+++ b/src/test/kotlin/com/coder/gateway/cli/CoderCLIManagerTest.kt
@@ -825,7 +825,7 @@ internal class CoderCLIManagerTest {
             listOf(
                 Pair("2.5.0", Features(true)),
                 Pair("2.13.0", Features(true, true)),
-                Pair("4.9.0", Features(true, true, true)),
+                Pair("4.9.0", Features(true, true, true, true)),
                 Pair("2.4.9", Features(false)),
                 Pair("1.0.1", Features(false)),
             )