setup script can communicate an error message to the end user

src/main/kotlin/com/coder/gateway/CoderGatewayConstants.kt

@@ -3,4 +3,5 @@ package com.coder.gateway
 object CoderGatewayConstants {
     const val GATEWAY_CONNECTOR_ID = "Coder.Gateway.Connector"
     const val GATEWAY_RECENT_CONNECTIONS_ID = "Coder.Gateway.Recent.Connections"
+    const val GATEWAY_SETUP_COMMAND_ERROR = "CODER_SETUP_ERROR"
 }

src/main/kotlin/com/coder/gateway/CoderRemoteConnectionHandle.kt

@@ -2,6 +2,7 @@
 
 package com.coder.gateway
 
+import com.coder.gateway.CoderGatewayConstants.GATEWAY_SETUP_COMMAND_ERROR
 import com.coder.gateway.cli.CoderCLIManager
 import com.coder.gateway.models.WorkspaceProjectIDE
 import com.coder.gateway.models.toIdeWithStatus
@@ -412,18 +413,16 @@ class CoderRemoteConnectionHandle {
     ) {
         if (setupCommand.isNotBlank()) {
             indicator.text = "Running setup command..."
-            try {
-                exec(workspace, setupCommand)
-            } catch (ex: Exception) {
-                if (!ignoreSetupFailure) {
-                    throw ex
-                }
-            }
+            processSetupCommand(
+                { exec(workspace, setupCommand) },
+                ignoreSetupFailure
+            )
         } else {
             logger.info("No setup command to run on ${workspace.hostname}")
         }
     }
 
+
     /**
      * Execute a command in the IDE's bin directory.
      * This exists since the accessor does not provide a generic exec.
@@ -523,5 +522,25 @@ class CoderRemoteConnectionHandle {
 
     companion object {
         val logger = Logger.getInstance(CoderRemoteConnectionHandle::class.java.simpleName)
+        fun processSetupCommand(
+            output: () -> String,
+            ignoreSetupFailure: Boolean
+        ) {
+            try {
+                val errorText = output
+                    .invoke()
+                    .lines()
+                    .firstOrNull { it.contains(GATEWAY_SETUP_COMMAND_ERROR) }
+                    ?.let { it.substring(it.indexOf(GATEWAY_SETUP_COMMAND_ERROR) + GATEWAY_SETUP_COMMAND_ERROR.length).trim() }
+
+                if (!errorText.isNullOrBlank()) {
+                    throw Exception(errorText)
+                }
+            } catch (ex: Exception) {
+                if (!ignoreSetupFailure) {
+                    throw ex
+                }
+            }
+        }
     }
 }

src/test/kotlin/com/coder/gateway/util/SetupCommandTest.kt

@@ -0,0 +1,47 @@
+package com.coder.gateway.util
+
+import com.coder.gateway.CoderRemoteConnectionHandle.Companion.processSetupCommand
+import org.junit.jupiter.api.Test
+import org.junit.jupiter.api.assertThrows
+import kotlin.test.assertEquals
+
+internal class SetupCommandTest {
+
+    @Test
+    fun executionErrors() {
+        assertEquals(
+            "Execution error",
+            assertThrows<Exception> {
+                processSetupCommand({ throw Exception("Execution error") }, false)
+            }.message
+        )
+        processSetupCommand({ throw Exception("Execution error") }, true)
+    }
+
+    @Test
+    fun setupScriptError() {
+        assertEquals(
+            "Your IDE is expired, please update",
+            assertThrows<Exception> {
+                processSetupCommand({
+                """
+                execution line 1    
+                execution line 2
+                CODER_SETUP_ERRORYour IDE is expired, please update
+                execution line 3    
+                """
+                }, false)
+            }.message
+        )
+
+        processSetupCommand({
+            """
+                execution line 1    
+                execution line 2
+                CODER_SETUP_ERRORYour IDE is expired, please update
+                execution line 3    
+                """
+        }, true)
+
+    }
+}