diff --git a/maestro-orchestra-models/src/main/java/maestro/orchestra/Commands.kt b/maestro-orchestra-models/src/main/java/maestro/orchestra/Commands.kt
index eed7c3d390..1cc4b1f244 100644
--- a/maestro-orchestra-models/src/main/java/maestro/orchestra/Commands.kt
+++ b/maestro-orchestra-models/src/main/java/maestro/orchestra/Commands.kt
@@ -265,7 +265,8 @@ data class TapOnElementCommand(
 ) : Command {
 
     override fun description(): String {
-        return label ?: "${tapOnDescription(longPress, repeat)} on ${selector.description()}"
+        val optional = if (optional) "(Optional) " else ""
+        return label ?: "${tapOnDescription(longPress, repeat)} on $optional${selector.description()}"
     }
 
     override fun evaluateScripts(jsEngine: JsEngine): TapOnElementCommand {
@@ -379,7 +380,8 @@ data class AssertConditionCommand(
     }
 
     override fun description(): String {
-        return label ?: "Assert that ${condition.description()}"
+        val optional = if (optional) "(Optional) " else ""
+        return label ?: "Assert that $optional${condition.description()}"
     }
 
     override fun evaluateScripts(jsEngine: JsEngine): Command {
diff --git a/maestro-orchestra/src/main/java/maestro/orchestra/Orchestra.kt b/maestro-orchestra/src/main/java/maestro/orchestra/Orchestra.kt
index 33b68efaae..70d233e20e 100644
--- a/maestro-orchestra/src/main/java/maestro/orchestra/Orchestra.kt
+++ b/maestro-orchestra/src/main/java/maestro/orchestra/Orchestra.kt
@@ -678,10 +678,21 @@ class Orchestra(
                     updateMetadata(command, metadata)
 
                     return@mapIndexed try {
-                        executeCommand(evaluatedCommand, config)
-                            .also {
-                                onCommandComplete(index, command)
-                            }
+                        try {
+                            executeCommand(evaluatedCommand, config)
+                                .also {
+                                    onCommandComplete(index, command)
+                                }
+                        } catch (exception: MaestroException) {
+                            val isOptional = command.asCommand()?.optional == true
+                            if (isOptional) throw CommandWarned(exception.message)
+                            else throw exception
+                        }
+                    } catch (ignored: CommandWarned) {
+                        // Swallow exception, but add a warning as an insight
+                        Insights.report(Insight(message = ignored.message, level = Insight.Level.WARNING))
+                        onCommandWarned(index, command)
+                        false
                     } catch (ignored: CommandSkipped) {
                         // Swallow exception
                         onCommandSkipped(index, command)