diff --git a/src/services/NoteCreator.test.ts b/src/services/NoteCreator.test.ts
index a7d5d81..10c2139 100644
--- a/src/services/NoteCreator.test.ts
+++ b/src/services/NoteCreator.test.ts
@@ -96,6 +96,24 @@ describe('NoteCreator.deriveTitle', () => {
         expect(NoteCreator.deriveTitle('Meeting: Q1 "plan" #person', '#person'))
             .toBe('Meeting Q1 plan');
     });
+
+    it('strips extra leading separator after task checkbox (iterative marker stripping)', () => {
+        // "- [ ] - content" — after stripping "- " and "[ ] ", another "- " remains
+        expect(NoteCreator.deriveTitle('- [ ] - some content #idea', '#idea'))
+            .toBe('some content');
+    });
+
+    it('strips timestamp prefix from title in task line with timestamp', () => {
+        // "- [ ] - 12:30 - content" — the timestamp should not appear in the entity name
+        expect(NoteCreator.deriveTitle('- [ ] - 12:30 - some content #idea', '#idea'))
+            .toBe('some content');
+    });
+
+    it('strips timestamp prefix when line has wikilink after timestamp', () => {
+        // "- [ ] - 12:30 - [[some text]] #idea" — entity name from wikilink text only
+        expect(NoteCreator.deriveTitle('- [ ] - 12:30 - [[some text]] #idea', '#idea'))
+            .toBe('some text');
+    });
 });
 
 // ---------------------------------------------------------------------------
diff --git a/src/services/NoteCreator.ts b/src/services/NoteCreator.ts
index 3c775ae..dae865c 100644
--- a/src/services/NoteCreator.ts
+++ b/src/services/NoteCreator.ts
@@ -81,10 +81,20 @@ export class NoteCreator {
         // Unwrap wikilinks: [[Alice]] → Alice, [[Alice|Alias]] → Alice
         s = s.replace(/\[\[([^\]|]+)(?:\|[^\]]+)?\]\]/g, '$1').trim();
 
-        // Strip leading list / task markers (same order as PatternMatcher)
-        s = s.replace(/^\d+[.)]\s*/, '').trim();   // "1. " / "1)"
-        s = s.replace(/^[-*+]\s*/, '').trim();     // "- " / "* " / "+ "
-        s = s.replace(/^\[[ xX]\]\s*/, '').trim(); // "[ ] " / "[x] "
+        // Strip leading list / task markers iteratively to handle nested formats
+        // such as "- [ ] - content" where a separator "- " follows the task marker.
+        let prev: string;
+        do {
+            prev = s;
+            s = s.replace(/^\d+[.)]\s*/, '').trim();   // "1. " / "1)"
+            s = s.replace(/^[-*+]\s*/, '').trim();     // "- " / "* " / "+ "
+            s = s.replace(/^\[[ xX]\]\s*/, '').trim(); // "[ ] " / "[x] "
+        } while (s !== prev);
+
+        // Strip a leading timestamp (e.g. "12:30" or "9:45") that may appear as a
+        // time annotation between list markers and the actual content, optionally
+        // followed by a separator dash ("12:30 - content" → "content").
+        s = s.replace(/^\d{1,2}:\d{2}\s*[-–]?\s*/, '').trim();
 
         s = s.replace(/\s+/g, ' ').trim();
 
@@ -103,10 +113,15 @@ export class NoteCreator {
         const re = NoteCreator.tagRegex(triggerTag);
         let s = lineText.replace(re, '$1').trim();
 
-        // Strip leading list / task markers (same order as PatternMatcher)
-        s = s.replace(/^\d+[.)]\s*/, '').trim();   // "1. " / "1)"
-        s = s.replace(/^[-*+]\s*/, '').trim();     // "- " / "* " / "+ "
-        s = s.replace(/^\[[ xX]\]\s*/, '').trim(); // "[ ] " / "[x] "
+        // Strip leading list / task markers iteratively to handle nested formats
+        // such as "- [ ] - content" where a separator "- " follows the task marker.
+        let prev: string;
+        do {
+            prev = s;
+            s = s.replace(/^\d+[.)]\s*/, '').trim();   // "1. " / "1)"
+            s = s.replace(/^[-*+]\s*/, '').trim();     // "- " / "* " / "+ "
+            s = s.replace(/^\[[ xX]\]\s*/, '').trim(); // "[ ] " / "[x] "
+        } while (s !== prev);
 
         return s.replace(/\s+/g, ' ').trim();
     }
diff --git a/src/services/PatternMatcher.test.ts b/src/services/PatternMatcher.test.ts
index 3178b4c..6391bbd 100644
--- a/src/services/PatternMatcher.test.ts
+++ b/src/services/PatternMatcher.test.ts
@@ -100,6 +100,18 @@ describe('PatternMatcher.match — Case 2 (full-line)', () => {
         it('line with plain text plus an embedded wikilink matches as full-line', () => {
             expect(pm.match('Met [[Sarah]] #person', [PERSON], CLEAR, allResolved)).toEqual(fullLine(PERSON));
         });
+
+        it('resolved wikilink with only a timestamp prefix returns null — timestamp is not meaningful content', () => {
+            // "- [ ] - 12:30 - [[some text]] #idea" where the link is resolved:
+            // the only surrounding content is a timestamp, which is not a useful entity title
+            expect(pm.match('- [ ] - 12:30 - [[some text]] #idea', [IDEA], CLEAR, allResolved)).toBeNull();
+        });
+
+        it('unresolved wikilink after timestamp in task item is detected as Case 1', () => {
+            // Even with a timestamp prefix, an unresolved wikilink must trigger Case 1
+            expect(pm.match('- [ ] - 12:30 - [[some text]] #idea', [IDEA], CLEAR, noneResolved))
+                .toEqual(unresolvedLink(IDEA, 'some text'));
+        });
     });
 
     // --- disabled ---
diff --git a/src/services/PatternMatcher.ts b/src/services/PatternMatcher.ts
index 37aa156..2295318 100644
--- a/src/services/PatternMatcher.ts
+++ b/src/services/PatternMatcher.ts
@@ -225,9 +225,21 @@ export class PatternMatcher {
     private hasMeaningfulContent(line: string, tag: string): boolean {
         let s = line.replace(this.tagRegex(tag), '$1').trim();
         s = s.replace(/\[\[[^\]]*\]\]/g, '').trim(); // strip wikilinks
-        s = s.replace(/^\d+[.)]\s*/, '').trim();   // ordered list: "1. " or "1)"
-        s = s.replace(/^[-*+]\s*/, '').trim();     // unordered list: "- ", "* ", "+ "
-        s = s.replace(/^\[[ xX]\]\s*/, '').trim(); // task checkbox: "[ ] " or "[x] "
+
+        // Strip leading list / task markers iteratively to handle nested formats
+        // such as "- [ ] - content" where a separator "- " follows the task marker.
+        let prev: string;
+        do {
+            prev = s;
+            s = s.replace(/^\d+[.)]\s*/, '').trim();   // ordered list: "1. " or "1)"
+            s = s.replace(/^[-*+]\s*/, '').trim();     // unordered list: "- ", "* ", "+ "
+            s = s.replace(/^\[[ xX]\]\s*/, '').trim(); // task checkbox: "[ ] " or "[x] "
+        } while (s !== prev);
+
+        // A leading timestamp (e.g. "12:30") used as a time annotation between markers
+        // and content is not considered meaningful for deriving an entity title.
+        s = s.replace(/^\d{1,2}:\d{2}\s*[-–]?\s*/, '').trim();
+
         return s.length > 0;
     }