diff --git a/src/Microdown-Toc/MicHTMLVisitor.extension.st b/src/Microdown-Toc/MicHTMLVisitor.extension.st
index 64750f5a..c1d3b695 100644
--- a/src/Microdown-Toc/MicHTMLVisitor.extension.st
+++ b/src/Microdown-Toc/MicHTMLVisitor.extension.st
@@ -1,12 +1,28 @@
 Extension { #name : 'MicHTMLVisitor' }
 
 { #category : '*Microdown-Toc' }
-MicHTMLVisitor >> visitTocEntry: aMicTocEntry [ 
-	
-	canvas tag
-		name: 'li';
-		with: [ 
-			aMicTocEntry header headerElements do: 
-						[:each | each accept: self] ].
-	canvas newLine
+MicHTMLVisitor >> visitTocEntry: aMicTocEntry [
+
+	aMicTocEntry isLeaf
+		ifTrue: [
+				canvas tag
+					name: 'li';
+					with: [
+						aMicTocEntry header headerElements do: [ :each |
+								each accept: self ] ].
+				canvas newLine ]
+		ifFalse: [
+				canvas tag
+					name: 'li';
+					with: [
+							aMicTocEntry header headerElements do: [ :each |
+									each accept: self ].
+							canvas newLine.
+							canvas tag
+								name: 'ol';
+								with: [
+										canvas newLine.
+										aMicTocEntry children do: [ :each | each accept: self ] ].
+							canvas newLine ].
+				canvas newLine ]
 ]
diff --git a/src/Microdown-Toc/MicTocBuilder.class.st b/src/Microdown-Toc/MicTocBuilder.class.st
index 6809ea7f..41a54840 100644
--- a/src/Microdown-Toc/MicTocBuilder.class.st
+++ b/src/Microdown-Toc/MicTocBuilder.class.st
@@ -3,18 +3,28 @@ Class {
 	#superclass : 'MicrodownVisitor',
 	#instVars : [
 		'tocItems',
-		'headerStack'
+		'headerStack',
+		'limit'
 	],
 	#category : 'Microdown-Toc',
 	#package : 'Microdown-Toc'
 }
 
 { #category : 'initialization' }
-MicTocBuilder >> initialize [ 
-	
+MicTocBuilder >> initialize [
+
 	super initialize.
 	tocItems := OrderedCollection new.
 	headerStack := Stack new.
+	limit := 6
+]
+
+{ #category : 'configure' }
+MicTocBuilder >> limitUpTo: anInteger [
+
+	(anInteger between: 1 and: 5) ifFalse: [
+		self error: 'Invalid input. Limit should be between 1 and 5' ].
+	limit := anInteger
 ]
 
 { #category : 'accessing' }
@@ -34,23 +44,30 @@ MicTocBuilder >> tocItems [
 { #category : 'visiting' }
 MicTocBuilder >> visitHeader: aMicHeader [
 
-	headerStack isEmpty 
-		ifTrue: [ 
-			| newTopLevelTocEnty |
-			newTopLevelTocEnty := MicTocEntry new for: aMicHeader.
-			headerStack push: newTopLevelTocEnty.
-			tocItems add: newTopLevelTocEnty.
+	| newTocEntry |
+	newTocEntry := MicTocEntry new for: aMicHeader.
+
+	aMicHeader level > limit ifTrue: [ ^ self ].
+
+	headerStack isEmpty ifTrue: [
+			headerStack push: newTocEntry.
+			tocItems add: newTocEntry.
 			^ self ].
+
 	aMicHeader level = headerStack top level
-		ifTrue: [ 
-			| newTopLevelTocEnty |
-			headerStack pop.
-			newTopLevelTocEnty := MicTocEntry new for: aMicHeader.
-			headerStack push: newTopLevelTocEnty.
-			tocItems add: newTopLevelTocEnty.
-			]
-		ifFalse: [ 
-			aMicHeader level > headerStack top level
-				ifTrue: [ 
-					headerStack top addChild: (MicTocEntry new for: aMicHeader) ] ]
+		ifTrue: [
+				headerStack pop.
+				headerStack isEmpty
+					ifTrue: [ tocItems add: newTocEntry ]
+					ifFalse: [ headerStack top addChild: newTocEntry ] ]
+		ifFalse: [
+				aMicHeader level > headerStack top level
+					ifTrue: [ headerStack top addChild: newTocEntry ]
+					ifFalse: [
+							[
+								headerStack isNotEmpty and: [
+									headerStack top level >= aMicHeader level ] ] whileTrue: [
+								headerStack pop ].
+							headerStack isEmpty ifTrue: [ tocItems add: newTocEntry ] ] ].
+	headerStack push: newTocEntry
 ]
diff --git a/src/Microdown-Toc/MicTocEntry.class.st b/src/Microdown-Toc/MicTocEntry.class.st
index 7b7b147b..b00aed15 100644
--- a/src/Microdown-Toc/MicTocEntry.class.st
+++ b/src/Microdown-Toc/MicTocEntry.class.st
@@ -43,6 +43,12 @@ MicTocEntry >> initialize [
 	children := OrderedCollection new
 ]
 
+{ #category : 'testing' }
+MicTocEntry >> isLeaf [
+
+	^ children isEmpty
+]
+
 { #category : 'accessing' }
 MicTocEntry >> level [
 	^ header level
diff --git a/src/Microdown-Toc/MicTocEntryTest.class.st b/src/Microdown-Toc/MicTocEntryTest.class.st
new file mode 100644
index 00000000..356c89db
--- /dev/null
+++ b/src/Microdown-Toc/MicTocEntryTest.class.st
@@ -0,0 +1,28 @@
+"
+A MicTocEntryTest is a test class for testing the behavior of MicTocEntry
+"
+Class {
+	#name : 'MicTocEntryTest',
+	#superclass : 'TestCase',
+	#category : 'Microdown-Toc',
+	#package : 'Microdown-Toc'
+}
+
+{ #category : 'tests' }
+MicTocEntryTest >> testWithChildrenIsNotLeaf [
+
+	| entry |
+	entry := MicTocEntry new.
+	entry addChild: MicTocEntry new.
+
+	self deny: entry isLeaf
+]
+
+{ #category : 'tests' }
+MicTocEntryTest >> testWithoutChildrenIsLeaf [
+
+	| entry |
+	entry := MicTocEntry new.
+
+	self assert: entry isLeaf
+]
diff --git a/src/Microdown-Toc/MicTocHTMLTest.class.st b/src/Microdown-Toc/MicTocHTMLTest.class.st
index aec5e3c5..89a7243d 100644
--- a/src/Microdown-Toc/MicTocHTMLTest.class.st
+++ b/src/Microdown-Toc/MicTocHTMLTest.class.st
@@ -40,3 +40,26 @@ MicTocHTMLTest >> testHTMLRender [
 '</ol>'
 
 ]
+
+{ #category : 'tests' }
+MicTocHTMLTest >> testHTMLRenderSimpleNesting [
+
+	| doc builder htmlVisitor |
+	doc := Microdown parse: '
+# Header1
+## Header11
+'.
+	builder := MicTocBuilder new.
+	builder visit: doc.
+	self assert: builder toc children first children isNotEmpty.
+
+	htmlVisitor := MicHTMLVisitor new.
+	htmlVisitor visit: builder toc.
+
+	self
+		assert: htmlVisitor contents
+		equals:
+			String crlf , '<ol>' , String crlf , '<li>Header1' , String crlf
+			, '<ol>' , String crlf , '<li>Header11</li>' , String crlf
+			, '</ol>' , String crlf , '</li>' , String crlf , '</ol>'
+]
diff --git a/src/Microdown-Toc/MicTocTest.class.st b/src/Microdown-Toc/MicTocTest.class.st
index a0c48e09..f06bc989 100644
--- a/src/Microdown-Toc/MicTocTest.class.st
+++ b/src/Microdown-Toc/MicTocTest.class.st
@@ -5,6 +5,192 @@ Class {
 	#package : 'Microdown-Toc'
 }
 
+{ #category : 'tests' }
+MicTocTest >> testAlternatingheaderLevels [
+
+	| doc builder topLevelTocItems |
+	doc := Microdown parse: '
+# Header1
+## Header11
+# Header2
+## Header21
+'.
+	builder := MicTocBuilder new.
+
+	builder visit: doc.
+
+	topLevelTocItems := builder tocItems.
+	self assert: builder tocItems size equals: 2.
+	self assert: topLevelTocItems first header text equals: 'Header1'.
+	self
+		assert: topLevelTocItems first children first header text
+		equals: 'Header11'.
+	self assert: topLevelTocItems second header text equals: 'Header2'.
+	self
+		assert: topLevelTocItems second children first header text
+		equals: 'Header21'
+]
+
+{ #category : 'tests' }
+MicTocTest >> testComplexDeeplyNestedEntries [
+
+	| doc builder |
+	doc := Microdown parse: '
+# Header1
+## Header11
+### Header111
+### Header112
+## Header12
+# Header2
+## Header21
+'.
+	builder := MicTocBuilder new.
+
+	builder visit: doc.
+
+	self assert: builder tocItems size equals: 2.
+	self assert: builder tocItems first header text equals: 'Header1'.
+	self
+		assert: builder tocItems first children first header text
+		equals: 'Header11'.
+	self
+		assert:
+		builder tocItems first children first children first header text
+		equals: 'Header111'.
+	self
+		assert:
+		builder tocItems first children first children second header text
+		equals: 'Header112'.
+	self assert: builder tocItems second header text equals: 'Header2'
+]
+
+{ #category : 'tests' }
+MicTocTest >> testLimitDepthToLevelOne [
+
+	| doc builder topLevelTocItems |
+	doc := Microdown parse: '
+# Header1
+## Header11
+# Header2
+## Header21
+'.
+	builder := MicTocBuilder new.
+
+	builder limitUpTo: 1.
+	builder visit: doc.
+
+	topLevelTocItems := builder tocItems.
+	self assert: builder tocItems size equals: 2.
+	self assert: topLevelTocItems first header text equals: 'Header1'.
+	self assert: topLevelTocItems first isLeaf.
+	self assert: topLevelTocItems second header text equals: 'Header2'.
+	self assert: topLevelTocItems second isLeaf
+]
+
+{ #category : 'tests' }
+MicTocTest >> testLimitDepthWithInvalidInput [
+
+	| builder should |
+	builder := MicTocBuilder new.
+	should := false.
+
+	[ builder limitUpTo: 0 ]
+		on: Error
+		do: [ :ex |
+				self
+					assert: ex description
+					equals: 'Error: Invalid input. Limit should be between 1 and 5'.
+				should := true ].
+	self assert: should
+]
+
+{ #category : 'tests' }
+MicTocTest >> testLimitDepthWithInvalidInput0 [
+
+	| builder should |
+	builder := MicTocBuilder new.
+	should := false.
+
+	[ builder limitUpTo: 0 ]
+		on: Error
+		do: [ :ex |
+				self
+					assert: ex description
+					equals: 'Error: Invalid input. Limit should be between 1 and 5'.
+				should := true ].
+	self assert: should
+]
+
+{ #category : 'tests' }
+MicTocTest >> testLimitDepthWithInvalidInput6 [
+
+	| builder should |
+	builder := MicTocBuilder new.
+	should := false.
+
+	[ builder limitUpTo: 6 ]
+		on: Error
+		do: [ :ex |
+				self
+					assert: ex description
+					equals: 'Error: Invalid input. Limit should be between 1 and 5'.
+				should := true ].
+	self assert: should
+]
+
+{ #category : 'tests' }
+MicTocTest >> testMalformedHeaderOrder [
+
+	| doc builder firstTocItem secondTocItem thirdTocItem |
+	doc := Microdown parse: '
+### Header001
+## Header01
+# Header1
+'.
+	builder := MicTocBuilder new.
+
+	builder visit: doc.
+
+	self assert: builder tocItems size equals: 3.
+	firstTocItem := builder tocItems first.
+	self assert: firstTocItem header text equals: 'Header001'.
+	self assertEmpty: firstTocItem children.
+	secondTocItem := builder tocItems second.
+	self assert: secondTocItem header text equals: 'Header01'.
+	self assertEmpty: secondTocItem children.
+	thirdTocItem := builder tocItems third.
+	self assert: thirdTocItem header text equals: 'Header1'.
+	self assertEmpty: thirdTocItem children
+]
+
+{ #category : 'tests' }
+MicTocTest >> testSimpleDeeplyNestedEntries [
+
+	| doc builder |
+	doc := Microdown parse: '
+# Header1
+## Header11
+### Header111
+#### Header1111
+'.
+	builder := MicTocBuilder new.
+	builder visit: doc.
+	self assert: builder tocItems size equals: 1.
+	self assert: builder tocItems first header text equals: 'Header1'.
+	self
+		assert: builder tocItems first children first header text
+		equals: 'Header11'.
+	self
+		assert:
+		builder tocItems first children first children first header text
+		equals: 'Header111'.
+	self
+		assert:
+			builder tocItems first children first children first children first
+				header text
+		equals: 'Header1111'
+]
+
 { #category : 'tests' }
 MicTocTest >> testSimpleFlatEntries [
 
@@ -49,3 +235,27 @@ lkhkhk
 	self assert: builder tocItems first children first header text equals: 'Header11'.
 
 ]
+
+{ #category : 'tests' }
+MicTocTest >> testTopLevelHeaderWithTwoSecondLevelHeaders [
+
+	| doc builder topLevelTocItem |
+	doc := Microdown parse: '
+# Header1
+## Header11
+## Header12
+'.
+	builder := MicTocBuilder new.
+
+	builder visit: doc.
+
+	topLevelTocItem := builder tocItems first.
+	self assert: builder tocItems size equals: 1.
+	self assert: topLevelTocItem header text equals: 'Header1'.
+	self
+		assert: topLevelTocItem children first header text
+		equals: 'Header11'.
+	self
+		assert: topLevelTocItem children second header text
+		equals: 'Header12'
+]