diff --git a/src/parser/parser.ts b/src/parser/parser.ts
index b61eb0de8..350505040 100644
--- a/src/parser/parser.ts
+++ b/src/parser/parser.ts
@@ -3,7 +3,11 @@ import { parseTimestamp } from "../timestamp/timestamp";
 import { timestampRegExp } from "../regexp";
 import { isTopLevelListItem } from "../../obsidian-metadata-utils/src/list";
 import { getTextAtPosition } from "../../obsidian-metadata-utils/src/position";
-import { getDiffInMinutes, getMinutesSinceMidnightTo, minutesToMoment } from "../util/moment";
+import {
+  getDiffInMinutes,
+  getMinutesSinceMidnightTo,
+  minutesToMoment,
+} from "../util/moment";
 import { DEFAULT_DURATION_MINUTES } from "../constants";
 import { getTimeFromYOffset, roundToSnapStep } from "src/store/timeline-store";
 import { getDailyNoteForToday } from "src/util/daily-notes";
@@ -40,6 +44,10 @@ export function parsePlanItems(
     planHeadingContent,
   );
 
+  if (!listItemsUnderPlan) {
+    return [];
+  }
+
   const listItemsWithContent = getListItemContent(content, listItemsUnderPlan);
 
   return listItemsWithContent
diff --git a/src/plan.ts b/src/plan.ts
index 5e13fa40a..4895959dc 100644
--- a/src/plan.ts
+++ b/src/plan.ts
@@ -25,18 +25,25 @@ export async function appendToPlan(path: string, planItem: PlanItem) {
 
   let result = replaceTimestamp(planItem, { ...planItem });
 
-  const headingMetadata = getHeadingByText(metadata, plannerHeading);
+  const headingLine = getHeadingByText(metadata, plannerHeading);
 
-  if (!headingMetadata) {
+  let line = editor.lastLine();
+
+  if (!headingLine) {
     result = `${createPlannerHeading()}\n\n${result}`;
+  } else {
+    line = headingLine.position.start.line;
   }
 
   const listItems = getListItemsUnderHeading(metadata, plannerHeading);
-  const lastListItem = listItems[listItems.length - 1];
 
-  const line = lastListItem
-    ? lastListItem.position.start.line
-    : editor.lastLine();
+  if (listItems?.length > 0) {
+    const lastListItem = listItems[listItems.length - 1];
+
+    line = lastListItem.position.start.line;
+  } else if (headingLine) {
+    result = `\n${result}`
+  }
 
   const ch = editor.getLine(line).length;
 
diff --git a/src/util/editor.ts b/src/util/editor.ts
index 1ce6a652c..7715e5e45 100644
--- a/src/util/editor.ts
+++ b/src/util/editor.ts
@@ -1,7 +1,7 @@
 import type { Editor } from "obsidian";
 
 export function selectText(editor: Editor, text: string) {
-  const startOffset = editor.getValue().indexOf(text);
+  const startOffset = editor.getValue().lastIndexOf(text);
   const endOffset = startOffset + text.length;
 
   editor.setSelection(