diff --git a/packages/kbn-monaco/scripts/utils/create_autocomplete_definitions.js b/packages/kbn-monaco/scripts/utils/create_autocomplete_definitions.js
index d6eeac2e20f61..3750b8697f493 100644
--- a/packages/kbn-monaco/scripts/utils/create_autocomplete_definitions.js
+++ b/packages/kbn-monaco/scripts/utils/create_autocomplete_definitions.js
@@ -36,7 +36,7 @@ const getDisplayName = (name, imported) => {
     displayName = name.split('.').pop() || name;
   }
 
-  return displayName.replace('$', '.');
+  return displayName.replace(/^\$/g, '.');
 };
 
 /**
diff --git a/packages/kbn-monaco/src/painless/worker/painless_worker.ts b/packages/kbn-monaco/src/painless/worker/painless_worker.ts
index 332199f45b8ee..80489ccdbc589 100644
--- a/packages/kbn-monaco/src/painless/worker/painless_worker.ts
+++ b/packages/kbn-monaco/src/painless/worker/painless_worker.ts
@@ -44,7 +44,7 @@ export class PainlessWorker implements BaseWorkerDefinition {
     fields?: PainlessAutocompleteField[]
   ): PainlessCompletionResult {
     // Array of the active line words, e.g., [boolean, isTrue, =, true]
-    const words = currentLineChars.replace('\t', '').split(' ');
+    const words = currentLineChars.replace(/\t/g, '').split(/\s/);
 
     const autocompleteSuggestions: PainlessCompletionResult = getAutocompleteSuggestions(
       context,