diff --git a/src/Commands/ToggleDone.ts b/src/Commands/ToggleDone.ts
index 877f2d40f2..91931dd99d 100644
--- a/src/Commands/ToggleDone.ts
+++ b/src/Commands/ToggleDone.ts
@@ -102,7 +102,7 @@ export const toggleLine = (line: string, path: string): EditorInsertion => {
             const statusString = regexMatch[3];
             const status = StatusRegistry.getInstance().bySymbol(statusString);
             const newStatusString = status.nextStatusSymbol;
-            return { text: line.replace(TaskRegularExpressions.taskRegex, `$1- [${newStatusString}] $4`) };
+            return { text: line.replace(TaskRegularExpressions.taskRegex, `$1$2 [${newStatusString}] $4`) };
         } else if (TaskRegularExpressions.listItemRegex.test(line)) {
             // Convert the list item to a checklist item.
             const text = line.replace(TaskRegularExpressions.listItemRegex, '$1$2 [ ]');
diff --git a/tests/Commands/ToggleDone.test.ts b/tests/Commands/ToggleDone.test.ts
index 1a3f19f0b1..68814e5e22 100644
--- a/tests/Commands/ToggleDone.test.ts
+++ b/tests/Commands/ToggleDone.test.ts
@@ -106,26 +106,32 @@ describe('ToggleDone', () => {
     it('should add checkbox to hyphen and space', () => {
         testToggleLine('|- ', '- [ ] |');
         testToggleLine('- |', '- [ ] |');
-        testToggleLine('- |foobar', '- [ ] foobar|');
+        testToggleLine('1. |foobar', '1. [ ] foobar|');
 
         GlobalFilter.getInstance().set('#task');
 
         testToggleLine('|- ', '- [ ] |');
         testToggleLine('- |', '- [ ] |');
-        testToggleLine('- |foobar', '- [ ] foobar|');
+        testToggleLine('1. |foobar', '1. [ ] foobar|');
     });
 
     it('should complete a task', () => {
         testToggleLine('|- [ ] ', '|- [x]  ✅ 2022-09-04');
         testToggleLine('- [ ] |', '- [x] | ✅ 2022-09-04');
+        testToggleLine('- [ ] description|', '- [x] description| ✅ 2022-09-04');
 
         // Issue #449 - cursor jumped 13 characters to the right on completion
         testToggleLine('- [ ] I have a |proper description', '- [x] I have a |proper description ✅ 2022-09-04');
 
         GlobalFilter.getInstance().set('#task');
 
+        // Done date is not added if task does not match global filter
         testToggleLine('|- [ ] ', '|- [x] ');
-        testToggleLine('- [ ] |', '- [x] |');
+        testToggleLine('1. [ ] |', '1. [x] |');
+
+        // Done date is added if task does not match global filter
+        testToggleLine('- [ ] #task|', '- [x]  #tas|k ✅ 2022-09-04'); // Extra space added before #; cursor moves left
+        testToggleLine('* [ ] #task description|', '* [x] #task description| ✅ 2022-09-04');
 
         // Issue #449 - cursor jumped 13 characters to the right on completion
         testToggleLine('- [ ] I have a |proper description', '- [x] I have a |proper description');
@@ -133,7 +139,7 @@ describe('ToggleDone', () => {
 
     it('should un-complete a completed task', () => {
         testToggleLine('|- [x]  ✅ 2022-09-04', '|- [ ] ');
-        testToggleLine('- [x]  ✅ 2022-09-04|', '- [ ] |');
+        testToggleLine('1. [x]  ✅ 2022-09-04|', '1. [ ] |');
 
         // Issue #449 - cursor jumped 13 characters to the left on un-completion
         testToggleLine('- [x] I have a proper description| ✅ 2022-09-04', '- [ ] I have a proper description|');
@@ -142,7 +148,11 @@ describe('ToggleDone', () => {
 
         // Done date is not removed if task does not match global filter
         testToggleLine('|- [x]  ✅ 2022-09-04', '|- [ ] ✅ 2022-09-04');
-        testToggleLine('- [x]  ✅ 2022-09-04|', '- [ ] ✅ 2022-09-04|');
+        testToggleLine('+ [x]  ✅ 2022-09-04|', '+ [ ] ✅ 2022-09-04|');
+
+        // Done date is added if task matches the global filter
+        testToggleLine('|- [x] #task ✅ 2022-09-04', '|- [ ]  #task'); // Extra space added before #
+        testToggleLine('1. [x] #task description ✅ 2022-09-04|', '1. [ ] #task description|');
 
         // Issue #449 - cursor jumped 13 characters to the left on un-completion
         testToggleLine(