diff --git a/package.json b/package.json
index b95e2c25e..be34a9618 100644
--- a/package.json
+++ b/package.json
@@ -1813,7 +1813,7 @@
 			"code-for-ibmi.debug.group": [
 				{
 					"command": "code-for-ibmi.debug.batch",
-					"when": "code-for-ibmi:debug"
+					"when": "code-for-ibmi:debug && viewItem =~ /^object.pgm.*/"
 				},
 				{
 					"command": "code-for-ibmi.debug.sep",
@@ -2297,7 +2297,7 @@
 			"editor/title": [
 				{
 					"submenu": "code-for-ibmi.debug.group",
-					"when": "code-for-ibmi:connected && !inDebugMode && editorLangId =~ /^rpgle$|^rpg$|^cobol$|^cl$/i",
+					"when": "code-for-ibmi:connected && editorLangId =~ /^rpgle$|^rpg$|^cobol$|^cl$/i",
 					"group": "navigation@1"
 				},
 				{
@@ -2499,7 +2499,7 @@
 				},
 				{
 					"submenu": "code-for-ibmi.debug.group",
-					"when": "view == objectBrowser && !inDebugMode && (viewItem =~ /^object.pgm.*/ || viewItem =~ /^object.srvpgm.*/)",
+					"when": "view == objectBrowser && viewItem =~ /^object.(pgm|srvpgm).*/",
 					"group": "2_debug@1"
 				},
 				{
diff --git a/src/api/debug/index.ts b/src/api/debug/index.ts
index e2a7747e6..a7dd5b6a0 100644
--- a/src/api/debug/index.ts
+++ b/src/api/debug/index.ts
@@ -254,7 +254,7 @@ export async function initialize(context: ExtensionContext) {
             if (objectType) {
               startDebugging(debugType, objectType, qualifiedObject.library, qualifiedObject.object, workspaceFolder);
             } else {
-              vscode.window.showErrorMessage(`Failed to determine object type. Ensure the object exists and is a program (*PGM) or service program (*SRVPGM).`);
+              vscode.window.showErrorMessage(`Failed to determine object type. Ensure the object exists and is a program (*PGM)${debugType === "sep" ? " or service program (*SRVPGM)" : ""}.`);
             }
           }
         } else {