diff --git a/docs/assets/example-highlights-order.png b/docs/assets/example-highlights-order.png
new file mode 100644
index 0000000..66c9462
Binary files /dev/null and b/docs/assets/example-highlights-order.png differ
diff --git a/docs/guide/settings.md b/docs/guide/settings.md
index 83078b5..7ece6b0 100644
--- a/docs/guide/settings.md
+++ b/docs/guide/settings.md
@@ -32,6 +32,127 @@ Backup highlights folder before import. The backup folder name is pre-configured
 > If the setting is disabled, the plugin will overwrite the contents of the [highlight folder](#highlight-folder) on import.
 > This behavior will be improved based on the feedback received: [Issue #34](https://github.com/bandantonio/obsidian-apple-books-highlights-plugin/issues/34#issuecomment-2231429171)
 
+## Highlights sorting criterion
+
+- Default value: By creation date (from oldest to newest)
+
+Sort highlight by a specific criterion.
+
+The available options are:
+
+- By creation date (from oldest to newest)
+- By creation date (from newest to oldest)
+- By last modification date* (from oldest to newest)
+- By last modification date* (from newest to oldest)
+- By location in a book
+
+::: tip What a modification is?
+Modification includes the following cases:
+
+- Updating highlight text
+- Adding or updating a note
+- Changing the highlight color or style
+:::
+
+::: details Examples
+
+Let's consider an example book with the following highlights (callouts to the left indicate the order in which the highlights were created):
+
+![Highlights order](../assets/example-highlights-order.png)
+
+- **By creation date (from oldest to newest)**: The highlights that were created first will be at the top.
+
+	::: details Example
+	```md
+	## Annotations
+	----
+	- 🎯 Highlight:: And now this. Christmas Day, alone on a hospital ward, failing to get through my shift.
+	----
+	- 🎯 Highlight:: At 10:30am, I looked around the ward. Nurse Janice was sprinting up and down corridor A
+	----
+	- 🎯 Highlight:: As Christmas turned to Boxing Day, I stayed up poring over my old notes and wondered whether that was where I was going wrong
+	----
+	- 🎯 Highlight:: ‘Merry Christmas, Ali. Try not to kill anyone.’
+	```
+	:::
+
+- **By creation date (from newest to oldest)**: The highlights that were created last will be at the top.
+
+	::: details Example
+	```md
+	## Annotations
+	----
+	- 🎯 Highlight:: ‘Merry Christmas, Ali. Try not to kill anyone.’
+	----
+	- 🎯 Highlight:: As Christmas turned to Boxing Day, I stayed up poring over my old notes and wondered whether that was where I was going wrong
+	----
+	- 🎯 Highlight:: At 10:30am, I looked around the ward. Nurse Janice was sprinting up and down corridor A
+	----
+	- 🎯 Highlight:: And now this. Christmas Day, alone on a hospital ward, failing to get through my shift.
+	```
+	:::
+
+- **By last modification date (from oldest to newest)**: The highlights that were modified first will be at the top.
+
+	::: details Example
+	```md
+	## Annotations
+	----
+	- 🎯 Highlight:: As Christmas turned to Boxing Day, I stayed up poring over my old notes and wondered whether that was where I was going wrong
+	- 📝 Note:: N/A
+	----
+	- 🎯 Highlight:: ‘Merry Christmas, Ali. Try not to kill anyone.’
+	- 📝 Note:: N/A
+	----
+	- 🎯 Highlight:: At 10:30am, I looked around the ward. Nurse Janice was sprinting up and down corridor A
+	- 📝 Note:: Test modification date (modified first)
+	----
+	- 🎯 Highlight:: And now this. Christmas Day, alone on a hospital ward, failing to get through my shift.
+	- 📝 Note:: Test modification date (modified second)
+	```
+	:::
+
+- **By last modification date (from newest to oldest)**: The highlights that were modified last will be at the top.
+
+	::: details Example
+	```md
+	## Annotations
+	----
+	- 🎯 Highlight:: And now this. Christmas Day, alone on a hospital ward, failing to get through my shift.
+	- 📝 Note:: Test modification date (modified second)
+	----
+	- 🎯 Highlight:: At 10:30am, I looked around the ward. Nurse Janice was sprinting up and down corridor A
+	- 📝 Note:: Test modification date (modified first)
+	----
+	- 🎯 Highlight:: ‘Merry Christmas, Ali. Try not to kill anyone.’
+	- 📝 Note:: N/A
+	----
+	- 🎯 Highlight:: As Christmas turned to Boxing Day, I stayed up poring over my old notes and wondered whether that was where I was going wrong
+	- 📝 Note:: N/A
+	```
+	:::
+
+- **By location in a book**: Highlights are sorted by their location in a book.
+
+	::: details Example
+	```md
+	## Annotations
+	----
+	- 🎯 Highlight:: ‘Merry Christmas, Ali. Try not to kill anyone.’
+	- 📝 Note:: N/A
+	----
+	- 🎯 Highlight:: At 10:30am, I looked around the ward. Nurse Janice was sprinting up and down corridor A
+	- 📝 Note:: Test modification date (modified first)
+	----
+	- 🎯 Highlight:: And now this. Christmas Day, alone on a hospital ward, failing to get through my shift.
+	- 📝 Note:: Test modification date (modified second)
+	----
+	- 🎯 Highlight:: As Christmas turned to Boxing Day, I stayed up poring over my old notes and wondered whether that was where I was going wrong
+	- 📝 Note:: N/A
+	```
+	:::
+:::
+
 ## Template
 
 - Template for highlight files.
diff --git a/src/methods/saveHighlightsToVault.ts b/src/methods/saveHighlightsToVault.ts
index 0c28f21..b55ea31 100644
--- a/src/methods/saveHighlightsToVault.ts
+++ b/src/methods/saveHighlightsToVault.ts
@@ -3,6 +3,7 @@ import path from 'path';
 import { ICombinedBooksAndHighlights } from '../types';
 import { AppleBooksHighlightsImportPluginSettings } from '../settings';
 import { renderHighlightsTemplate } from './renderHighlightsTemplate';
+import { sortHighlights } from 'src/methods/sortHighlights';
 
 export default class SaveHighlights {
 	private app: App;
@@ -43,9 +44,13 @@ export default class SaveHighlights {
 
 		await this.vault.createFolder(this.settings.highlightsFolder);
 
-		highlights.forEach(async (highlight: ICombinedBooksAndHighlights) => {
-			const renderedTemplate = await renderHighlightsTemplate(highlight, this.settings.template);
-			const filePath = path.join(this.settings.highlightsFolder, `${highlight.bookTitle}.md`);
+		highlights.forEach(async (combinedHighlight: ICombinedBooksAndHighlights) => {
+			// Order highlights according to the value in settings
+			const sortedHighlights = sortHighlights(combinedHighlight, this.settings.highlightsSortingCriterion);
+
+			// Save highlights to vault
+			const renderedTemplate = await renderHighlightsTemplate(sortedHighlights, this.settings.template);
+			const filePath = path.join(this.settings.highlightsFolder, `${combinedHighlight.bookTitle}.md`);
 
 			await this.vault.create(
 				filePath,
diff --git a/src/methods/sortHighlights.ts b/src/methods/sortHighlights.ts
new file mode 100644
index 0000000..fec9014
--- /dev/null
+++ b/src/methods/sortHighlights.ts
@@ -0,0 +1,62 @@
+import { IHighlight, ICombinedBooksAndHighlights, IHighlightsSortingCriterion } from 'src/types';
+
+export const sortHighlights = (combinedHighlight: ICombinedBooksAndHighlights, highlightsSortingCriterion: string) => {
+	let sortedHighlights: IHighlight[] = [];
+
+	switch (highlightsSortingCriterion) {
+		case IHighlightsSortingCriterion.CreationDateOldToNew:
+			sortedHighlights = combinedHighlight.annotations.sort((a, b) => a.highlightCreationDate - b.highlightCreationDate);
+			break;
+		case IHighlightsSortingCriterion.CreationDateNewToOld:
+			sortedHighlights = combinedHighlight.annotations.sort((a, b) => b.highlightCreationDate - a.highlightCreationDate);
+			break;
+		case IHighlightsSortingCriterion.LastModifiedDateOldToNew:
+			sortedHighlights = combinedHighlight.annotations.sort((a, b) => a.highlightModificationDate - b.highlightModificationDate);
+			break;
+		case IHighlightsSortingCriterion.LastModifiedDateNewToOld:
+			sortedHighlights = combinedHighlight.annotations.sort((a, b) => b.highlightModificationDate - a.highlightModificationDate);
+			break;
+		case IHighlightsSortingCriterion.Book:
+			sortedHighlights = combinedHighlight.annotations.sort((a, b) => {
+				const firstHighlightLocation = highlightLocationToNumber(a.highlightLocation);
+				const secondHighlightLocation = highlightLocationToNumber(b.highlightLocation);
+
+				return compareLocations(firstHighlightLocation, secondHighlightLocation);
+			});
+			break;
+	}
+
+	return {
+		...combinedHighlight,
+		annotations: sortedHighlights
+	};
+}
+
+// The function converts a highlight location string to an array of numbers
+export const highlightLocationToNumber = (highlightLocation: string): number[] => {
+	// epubcfi example structure: epubcfi(/6/2[body01]!/4/2/2/1:0)
+	return highlightLocation
+		.slice(8, -1)	// Get rid of the epubcfi() wrapper
+		.split(',')		// Split the locator into three parts: the common parent, the start subpath, and the end subpath
+		.slice(0, -1)	// Get rid of the end subpath (third part)
+		.join(',')		// Join the first two parts back together
+		.match(/(?<!\[)[/:]\d+(?!\])/g)!  		 // Extract all the numbers (except those in square brackets) from the first two parts
+		.map(match => parseInt(match.slice(1)))	 // Get rid of the leading slash or colon and convert the string to a number
+}
+
+// The function performs lexicographic comparison of two locations to determine their relative position in a book
+export const compareLocations = (firstLocation: number[], secondLocation: number[]) => {
+	// Loop through each element of both arrays up to the length of the shorter one
+	for (let i = 0; i < Math.min(firstLocation.length, secondLocation.length); i++) {
+		if (firstLocation[i] < secondLocation[i]) {
+			return -1;
+		}
+		if (firstLocation[i] > secondLocation[i]) {
+			return 1;
+		}
+	}
+
+	// If the loop didn't return, the arrays are equal up to the length of the shorter array
+	// so the function returns the difference in lengths to determine the order of the corresponding locations
+	return firstLocation.length - secondLocation.length;
+}
diff --git a/src/settings.ts b/src/settings.ts
index a508f1d..3e51e5d 100644
--- a/src/settings.ts
+++ b/src/settings.ts
@@ -1,11 +1,13 @@
 import { App, Notice, PluginSettingTab, Setting } from 'obsidian';
 import IBookHighlightsPlugin from '../main';
 import defaultTemplate from './template';
+import { IHighlightsSortingCriterion, IBookHighlightsPluginSettings } from './types';
 
-export class AppleBooksHighlightsImportPluginSettings {
+export class AppleBooksHighlightsImportPluginSettings implements IBookHighlightsPluginSettings {
 	highlightsFolder = 'ibooks-highlights';
 	backup = false;
 	importOnStart = false;
+	highlightsSortingCriterion = IHighlightsSortingCriterion.CreationDateOldToNew;
 	template = defaultTemplate;
 }
 
@@ -66,6 +68,31 @@ export class IBookHighlightsSettingTab extends PluginSettingTab {
                     });
             });
 
+		new Setting(containerEl)
+			.setName('Highlights sorting criterion')
+			.setDesc('Sort highlights by a specific criterion. Default: By creation date (from oldest to newest)')
+			.setClass('ibooks-highlights-sorting')
+			.addDropdown((dropdown) => {
+				const options = {
+					[IHighlightsSortingCriterion.CreationDateOldToNew]: 'By creation date (from oldest to newest)',
+					[IHighlightsSortingCriterion.CreationDateNewToOld]: 'By creation date (from newest to oldest)',
+					[IHighlightsSortingCriterion.LastModifiedDateOldToNew]: 'By modification date (from oldest to newest)',
+					[IHighlightsSortingCriterion.LastModifiedDateNewToOld]: 'By modification date (from newest to oldest)',
+					[IHighlightsSortingCriterion.Book]: 'By location in a book'
+				};
+
+				dropdown
+					.addOptions(options)
+					.setValue(this.plugin.settings.highlightsSortingCriterion)
+					.onChange(async (value: IHighlightsSortingCriterion) => {
+						console.log('value', value);
+
+						this.plugin.settings.highlightsSortingCriterion = value;
+						await this.plugin.saveSettings();
+					}
+				);
+			});
+
         new Setting(containerEl)
             .setName('Template')
             .setDesc('Template for highlight files')
diff --git a/src/types.ts b/src/types.ts
index 5e2640f..8f52b33 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -1,3 +1,5 @@
+import { Template } from 'handlebars';
+
 export interface IBook {
     ZASSETID: string;
     ZTITLE: string;
@@ -40,3 +42,19 @@ export interface ICombinedBooksAndHighlights {
     bookCoverUrl: string;
     annotations: IHighlight[];
 }
+
+export enum IHighlightsSortingCriterion {
+	CreationDateOldToNew = 'creationDateOldToNew',
+	CreationDateNewToOld = 'creationDateNewToOld',
+	LastModifiedDateOldToNew = 'lastModifiedDateOldToNew',
+	LastModifiedDateNewToOld = 'lastModifiedDateNewToOld',
+	Book = 'book'
+}
+
+export interface IBookHighlightsPluginSettings {
+	highlightsFolder: string;
+	backup: boolean;
+	importOnStart: boolean;
+	highlightsSortingCriterion: IHighlightsSortingCriterion;
+	template: Template;
+}
diff --git a/src/utils/helpers.ts b/src/utils/helpers.ts
index 7ba8ad1..11108f0 100644
--- a/src/utils/helpers.ts
+++ b/src/utils/helpers.ts
@@ -3,8 +3,22 @@ import utc from 'dayjs/plugin/utc';
 import timezone from 'dayjs/plugin/timezone';
 import Handlebars from 'handlebars';
 
+export const calculateAppleDate = (date: number) => {
+	dayjs.extend(utc);
+	dayjs.extend(timezone);
+
+	const timeZone = dayjs.tz.guess();
+
+	const APPLE_EPOCH_START = new Date('2001-01-01').getTime();
+	const dateInMilliseconds = date * 1000;
+	const calculatedDate = dayjs(APPLE_EPOCH_START)
+		.add(dateInMilliseconds, 'ms')
+		.tz(timeZone || 'UTC');
+
+	return calculatedDate;
+}
+
 (() => {
-// TODO: Consider moving to a separate file if there are several helpers to be added
 	Handlebars.registerHelper('eq', function (a, b) {
 		if (a == b) {
 			return this;
@@ -13,17 +27,7 @@ import Handlebars from 'handlebars';
 
 	// TODO: Consider using out-of-the-box date validation via https://day.js.org/docs/en/parse/is-valid
 	Handlebars.registerHelper('dateFormat', (date, format) => {
-		dayjs.extend(utc);
-		dayjs.extend(timezone);
-
-		const timeZone = dayjs.tz.guess();
-
-		const APPLE_EPOCH_START = new Date('2001-01-01').getTime();
-		const dateInMilliseconds = date * 1000;
-		const calculatedDate = dayjs(APPLE_EPOCH_START)
-			.add(dateInMilliseconds, 'ms')
-			.tz(timeZone || 'UTC');
-
+		const calculatedDate = calculateAppleDate(date);
 		const formattedDate = calculatedDate.format(format);
 
 		return formattedDate;
diff --git a/test/aggregateDetails.spec.ts b/test/aggregateDetails.spec.ts
index f0c9ab0..9a20598 100644
--- a/test/aggregateDetails.spec.ts
+++ b/test/aggregateDetails.spec.ts
@@ -1,17 +1,17 @@
 import { describe, expect, test, vi } from 'vitest';
 import { aggregateBookAndHighlightDetails } from '../src/methods/aggregateDetails';
 import * as db from '../src/db';
-import { booksToAggregate, annotationsToAggregate, aggregatedHighlights } from './mocks/aggregatedDetailsData';
+import { booksToAggregate, annotationsToAggregate, aggregatedUnsortedHighlights } from './mocks/aggregatedDetailsData';
 import { IBook, IBookAnnotation } from '../src/types';
 
 describe('aggregateBookAndHighlightDetails', () => {
-	test('Should return an array of aggregated highlights when a book has highlights', async () => {
+	test('Should return an array of aggregated unsorted highlights when a book has highlights', async () => {
 		vi.spyOn(db, 'dbRequest').mockResolvedValue(booksToAggregate as IBook[]);
 		vi.spyOn(db, 'annotationsRequest').mockResolvedValue(annotationsToAggregate as IBookAnnotation[]);
 
 		const books = await aggregateBookAndHighlightDetails();
 
-		expect(books).toEqual(aggregatedHighlights);
+		expect(books).toEqual(aggregatedUnsortedHighlights);
 	});
 
 	test('Should return an empty array when a book has no highlights', async () => {
diff --git a/test/mocks/aggregatedDetailsData.ts b/test/mocks/aggregatedDetailsData.ts
index 9045c7b..caecc39 100644
--- a/test/mocks/aggregatedDetailsData.ts
+++ b/test/mocks/aggregatedDetailsData.ts
@@ -4,59 +4,133 @@ export const booksToAggregate = [{
 	"ZAUTHOR": "Apple Inc.",
 	"ZGENRE": "Technology",
 	"ZLANGUAGE": "EN",
-	"ZLASTOPENDATE": 731876693.002279,
+	"ZLASTOPENDATE": 743629954.550869,
 	"ZCOVERURL": ''
 }];
 
-export const annotationsToAggregate = [{
-	"ZANNOTATIONASSETID": "THBFYNJKTGFTTVCGSAE5",
-	"ZFUTUREPROOFING5": "Aggregated Introduction",
-	"ZANNOTATIONREPRESENTATIVETEXT": "This is a contextual text for the aggregated highlight from the Apple iPhone User Guide",
-	"ZANNOTATIONSELECTEDTEXT": "aggregated highlight from the Apple iPhone User Guide",
-	"ZANNOTATIONLOCATION": "aggregated-highlight-link-from-the-apple-iphone-user-guide",
-	"ZANNOTATIONNOTE": "Test note for the aggregated highlight from the Apple iPhone User Guide",
-	"ZANNOTATIONCREATIONDATE": 731876693.002279,
-	"ZANNOTATIONMODIFICATIONDATE": 731876693.002279,
-	"ZANNOTATIONSTYLE": 3,
-	"ZANNOTATIONDELETED": 0
-}, {
-	"ZANNOTATIONASSETID": "THBFYNJKTGFTTVCGSAE5",
-	"ZFUTUREPROOFING5": "Another aggregated Introduction",
-	"ZANNOTATIONREPRESENTATIVETEXT": "This is a contextual text for the aggregated highlight from the Apple iPhone User Guide\n\ncontaining a new line to test the preservation of indentation",
-	"ZANNOTATIONSELECTEDTEXT": "aggregated highlight from the Apple iPhone User Guide\n\ncontaining a new line to test the preservation of indentation\n\nand another new line\n\nto check one more time",
-	"ZANNOTATIONLOCATION": "aggregated-highlight-link-from-the-apple-iphone-user-guide",
-	"ZANNOTATIONNOTE": "Test note for the aggregated highlight from the Apple iPhone User Guide\n\nalong with a new line to test the preservation of indentation",
-	"ZANNOTATIONCREATIONDATE": 731876693.002279,
-	"ZANNOTATIONMODIFICATIONDATE": 731876693.002279,
-	"ZANNOTATIONSTYLE": 3,
-	"ZANNOTATIONDELETED": 0
+export const annotationsToAggregate = [
+	{
+		"ZANNOTATIONASSETID": "THBFYNJKTGFTTVCGSAE5",
+		"ZFUTUREPROOFING5": "Aggregated Introduction 3",
+		"ZANNOTATIONREPRESENTATIVETEXT": "This is a contextual text for the third aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONSELECTEDTEXT": "third aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONLOCATION": "epubcfi(/6/24[ch3]!/4/2/10,/1:19,/3:113)",
+		"ZANNOTATIONNOTE": "Test note for the third aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONCREATIONDATE": 743629925.898202,
+		"ZANNOTATIONMODIFICATIONDATE": 743640744.124985,
+		"ZANNOTATIONSTYLE": 3,
+		"ZANNOTATIONDELETED": 0
+	},
+	{
+		"ZANNOTATIONASSETID": "THBFYNJKTGFTTVCGSAE5",
+		"ZFUTUREPROOFING5": "Aggregated Introduction 1",
+		"ZANNOTATIONREPRESENTATIVETEXT": "This is a contextual text for the first aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONSELECTEDTEXT": "first aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONLOCATION": "epubcfi(/6/12[ch1]!/4/2/10,/1:0,/:87)",
+		"ZANNOTATIONNOTE": "Test note for the first aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONCREATIONDATE": 743629954.550827,
+		"ZANNOTATIONMODIFICATIONDATE": 743629954.550869,
+		"ZANNOTATIONSTYLE": 3,
+		"ZANNOTATIONDELETED": 0
+	},
+	{
+		"ZANNOTATIONASSETID": "THBFYNJKTGFTTVCGSAE5",
+		"ZFUTUREPROOFING5": "Aggregated Introduction 4",
+		"ZANNOTATIONREPRESENTATIVETEXT": "This is a contextual text for the fourth aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONSELECTEDTEXT": "fourth aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONLOCATION": "epubcfi(/6/36[ch4]!/10/2/4,/1:0,/:96)",
+		"ZANNOTATIONNOTE": "Test note for the fourth aggregated highlight from the Apple iPhone User Guide",
+		"ZANNOTATIONCREATIONDATE": 743629949.224146,
+		"ZANNOTATIONMODIFICATIONDATE": 743629949.224197,
+		"ZANNOTATIONSTYLE": 3,
+		"ZANNOTATIONDELETED": 0
+	},
+	{
+		"ZANNOTATIONASSETID": "THBFYNJKTGFTTVCGSAE5",
+		"ZFUTUREPROOFING5": "Aggregated Introduction 2",
+		"ZANNOTATIONREPRESENTATIVETEXT": "This is a contextual text for the second aggregated highlight from the Apple iPhone User Guide\n\ncontaining a new line to test the preservation of indentation",
+		"ZANNOTATIONSELECTEDTEXT": "second aggregated highlight from the Apple iPhone User Guide\n\ncontaining a new line to test the preservation of indentation\n\nand another new line\n\nto check one more time",
+		"ZANNOTATIONLOCATION": "epubcfi(/6/18[ch2]!/4/2/10,/4/1:19,/3:113)",
+		"ZANNOTATIONNOTE": "Test note for the second aggregated highlight from the Apple iPhone User Guide\n\nalong with a new line to test the preservation of indentation",
+		"ZANNOTATIONCREATIONDATE": 743629937.38764,
+		"ZANNOTATIONMODIFICATIONDATE": 743640715.281904,
+		"ZANNOTATIONSTYLE": 3,
+		"ZANNOTATIONDELETED": 0
+	},
+];
+
+export const annotationThree = {
+	"chapter": "Aggregated Introduction 3",
+	"contextualText": "This is a contextual text for the third aggregated highlight from the Apple iPhone User Guide",
+	"highlight": "third aggregated highlight from the Apple iPhone User Guide",
+	"note": "Test note for the third aggregated highlight from the Apple iPhone User Guide",
+	"highlightLocation": "epubcfi(/6/24[ch3]!/4/2/10,/1:19,/3:113)",
+	"highlightStyle": 3,
+	"highlightCreationDate": 743629925.898202,
+	"highlightModificationDate": 743640744.124985
+};
+
+export const annotationOne = {
+	"chapter": "Aggregated Introduction 1",
+	"contextualText": "This is a contextual text for the first aggregated highlight from the Apple iPhone User Guide",
+	"highlight": "first aggregated highlight from the Apple iPhone User Guide",
+	"note": "Test note for the first aggregated highlight from the Apple iPhone User Guide",
+	"highlightLocation": "epubcfi(/6/12[ch1]!/4/2/10,/1:0,/:87)",
+	"highlightStyle": 3,
+	"highlightCreationDate": 743629954.550827,
+	"highlightModificationDate": 743629954.550869
+};
+
+export const annotationFour = {
+	"chapter": "Aggregated Introduction 4",
+	"contextualText": "This is a contextual text for the fourth aggregated highlight from the Apple iPhone User Guide",
+	"highlight": "fourth aggregated highlight from the Apple iPhone User Guide",
+	"note": "Test note for the fourth aggregated highlight from the Apple iPhone User Guide",
+	"highlightLocation": "epubcfi(/6/36[ch4]!/10/2/4,/1:0,/:96)",
+	"highlightStyle": 3,
+	"highlightCreationDate": 743629949.224146,
+	"highlightModificationDate": 743629949.224197
+};
+
+export const annotationTwo = {
+	"chapter": "Aggregated Introduction 2",
+	"contextualText": "This is a contextual text for the second aggregated highlight from the Apple iPhone User Guide\ncontaining a new line to test the preservation of indentation",
+	"highlight": "second aggregated highlight from the Apple iPhone User Guide\ncontaining a new line to test the preservation of indentation\nand another new line\nto check one more time",
+	"note": "Test note for the second aggregated highlight from the Apple iPhone User Guide\nalong with a new line to test the preservation of indentation",
+	"highlightLocation": "epubcfi(/6/18[ch2]!/4/2/10,/4/1:19,/3:113)",
+	"highlightStyle": 3,
+	"highlightCreationDate": 743629937.38764,
+	"highlightModificationDate": 743640715.281904
+};
+
+export const aggregatedUnsortedHighlights = [{
+	"bookTitle": "Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title",
+	"bookId": "THBFYNJKTGFTTVCGSAE5",
+	"bookAuthor": "Apple Inc.",
+	"bookGenre": "Technology",
+	"bookLanguage": "EN",
+	"bookLastOpenedDate": 743629954.550869,
+	"bookCoverUrl": '',
+	"annotations": [
+		annotationThree,
+		annotationOne,
+		annotationFour,
+		annotationTwo,
+	]
 }];
 
-export const aggregatedHighlights = [{
+export const aggregatedHighlightsWithDefaultSorting = [{
 	"bookTitle": "Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title",
 	"bookId": "THBFYNJKTGFTTVCGSAE5",
 	"bookAuthor": "Apple Inc.",
 	"bookGenre": "Technology",
 	"bookLanguage": "EN",
-	"bookLastOpenedDate": 731876693.002279,
+	"bookLastOpenedDate": 743629954.550869,
 	"bookCoverUrl": '',
-	"annotations": [{
-		"chapter": "Aggregated Introduction",
-		"contextualText": "This is a contextual text for the aggregated highlight from the Apple iPhone User Guide",
-		"highlight": "aggregated highlight from the Apple iPhone User Guide",
-		"note": "Test note for the aggregated highlight from the Apple iPhone User Guide",
-		"highlightLocation": "aggregated-highlight-link-from-the-apple-iphone-user-guide",
-		"highlightStyle": 3,
-		"highlightCreationDate": 731876693.002279,
-		"highlightModificationDate": 731876693.002279
-	}, {
-		"chapter": "Another aggregated Introduction",
-		"contextualText": "This is a contextual text for the aggregated highlight from the Apple iPhone User Guide\ncontaining a new line to test the preservation of indentation",
-		"highlight": "aggregated highlight from the Apple iPhone User Guide\ncontaining a new line to test the preservation of indentation\nand another new line\nto check one more time",
-		"note": "Test note for the aggregated highlight from the Apple iPhone User Guide\nalong with a new line to test the preservation of indentation",
-		"highlightLocation": "aggregated-highlight-link-from-the-apple-iphone-user-guide",
-		"highlightStyle": 3,
-		"highlightCreationDate": 731876693.002279,
-		"highlightModificationDate": 731876693.002279
-	}]
+	"annotations": [
+		annotationThree,
+		annotationTwo,
+		annotationFour,
+		annotationOne,
+	]
 }];
diff --git a/test/mocks/renderedTemplate.ts b/test/mocks/renderedTemplate.ts
index 5e5e78f..e6410d5 100644
--- a/test/mocks/renderedTemplate.ts
+++ b/test/mocks/renderedTemplate.ts
@@ -1,71 +1,121 @@
-export const defaultTemplateMock = `Title:: 📕 Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title
+const renderedAnnotationThree = `- 📖 Chapter:: Aggregated Introduction 3
+- 🔖 Context:: This is a contextual text for the third aggregated highlight from the Apple iPhone User Guide
+- 🎯 Highlight:: third aggregated highlight from the Apple iPhone User Guide
+- 📝 Note:: Test note for the third aggregated highlight from the Apple iPhone User Guide
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/24[ch3]!/4/2/10,/1:19,/3:113))`;
+
+const renderedAnnotationOne = `- 📖 Chapter:: Aggregated Introduction 1
+- 🔖 Context:: This is a contextual text for the first aggregated highlight from the Apple iPhone User Guide
+- 🎯 Highlight:: first aggregated highlight from the Apple iPhone User Guide
+- 📝 Note:: Test note for the first aggregated highlight from the Apple iPhone User Guide
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/12[ch1]!/4/2/10,/1:0,/:87))`;
+
+const renderedAnnotationFour = `- 📖 Chapter:: Aggregated Introduction 4
+- 🔖 Context:: This is a contextual text for the fourth aggregated highlight from the Apple iPhone User Guide
+- 🎯 Highlight:: fourth aggregated highlight from the Apple iPhone User Guide
+- 📝 Note:: Test note for the fourth aggregated highlight from the Apple iPhone User Guide
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/36[ch4]!/10/2/4,/1:0,/:96))`;
+
+const renderedAnnotationTwo = `- 📖 Chapter:: Aggregated Introduction 2
+- 🔖 Context:: This is a contextual text for the second aggregated highlight from the Apple iPhone User Guide\ncontaining a new line to test the preservation of indentation
+- 🎯 Highlight:: second aggregated highlight from the Apple iPhone User Guide
+containing a new line to test the preservation of indentation
+and another new line
+to check one more time
+- 📝 Note:: Test note for the second aggregated highlight from the Apple iPhone User Guide
+along with a new line to test the preservation of indentation
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/18[ch2]!/4/2/10,/4/1:19,/3:113))`;
+
+export const defaultTemplateMockWithAnnotationsSortedByDefault = `Title:: 📕 Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title
 Author:: Apple Inc.
 Link:: [Apple Books Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5)
 
 ## Annotations
 
-Number of annotations:: 2
+Number of annotations:: 4
 
 ----
 
-- 📖 Chapter:: Aggregated Introduction
-- 🔖 Context:: This is a contextual text for the aggregated highlight from the Apple iPhone User Guide
-- 🎯 Highlight:: aggregated highlight from the Apple iPhone User Guide
-- 📝 Note:: Test note for the aggregated highlight from the Apple iPhone User Guide
-- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#aggregated-highlight-link-from-the-apple-iphone-user-guide)
+${renderedAnnotationThree}
 
 ----
 
-- 📖 Chapter:: Another aggregated Introduction
-- 🔖 Context:: This is a contextual text for the aggregated highlight from the Apple iPhone User Guide
-containing a new line to test the preservation of indentation
-- 🎯 Highlight:: aggregated highlight from the Apple iPhone User Guide
+${renderedAnnotationTwo}
+
+----
+
+${renderedAnnotationFour}
+
+----
+
+${renderedAnnotationOne}
+
+`;
+
+const renderedColoredAnnotationThree = `- 📖 Chapter:: Aggregated Introduction 3
+- 🔖 Context:: This is a contextual text for the third aggregated highlight from the Apple iPhone User Guide
+- 🎯 Highlight:: <mark style="background:rgb(249,213,108); color:#000; padding:2px;">third aggregated highlight from the Apple iPhone User Guide</mark>
+- 📝 Note:: Test note for the third aggregated highlight from the Apple iPhone User Guide
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/24[ch3]!/4/2/10,/1:19,/3:113))
+- <small>📅 Highlight taken on:: 2024-07-25 03:52:05 PM -04:00</small>
+- <small>📅 Highlight modified on:: 2024-07-25 06:52:24 PM -04:00</small>`;
+
+const renderedColoredAnnotationOne = `- 📖 Chapter:: Aggregated Introduction 1
+- 🔖 Context:: This is a contextual text for the first aggregated highlight from the Apple iPhone User Guide
+- 🎯 Highlight:: <mark style="background:rgb(249,213,108); color:#000; padding:2px;">first aggregated highlight from the Apple iPhone User Guide</mark>
+- 📝 Note:: Test note for the first aggregated highlight from the Apple iPhone User Guide
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/12[ch1]!/4/2/10,/1:0,/:87))
+- <small>📅 Highlight taken on:: 2024-07-25 03:52:34 PM -04:00</small>
+- <small>📅 Highlight modified on:: 2024-07-25 03:52:34 PM -04:00</small>`;
+
+const renderedColoredAnnotationFour = `- 📖 Chapter:: Aggregated Introduction 4
+- 🔖 Context:: This is a contextual text for the fourth aggregated highlight from the Apple iPhone User Guide
+- 🎯 Highlight:: <mark style="background:rgb(249,213,108); color:#000; padding:2px;">fourth aggregated highlight from the Apple iPhone User Guide</mark>
+- 📝 Note:: Test note for the fourth aggregated highlight from the Apple iPhone User Guide
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/36[ch4]!/10/2/4,/1:0,/:96))
+- <small>📅 Highlight taken on:: 2024-07-25 03:52:29 PM -04:00</small>
+- <small>📅 Highlight modified on:: 2024-07-25 03:52:29 PM -04:00</small>`;
+
+const renderedColoredAnnotationTwo = `- 📖 Chapter:: Aggregated Introduction 2
+- 🔖 Context:: This is a contextual text for the second aggregated highlight from the Apple iPhone User Guide\ncontaining a new line to test the preservation of indentation
+- 🎯 Highlight:: <mark style="background:rgb(249,213,108); color:#000; padding:2px;">second aggregated highlight from the Apple iPhone User Guide
 containing a new line to test the preservation of indentation
 and another new line
-to check one more time
-- 📝 Note:: Test note for the aggregated highlight from the Apple iPhone User Guide
+to check one more time</mark>
+- 📝 Note:: Test note for the second aggregated highlight from the Apple iPhone User Guide
 along with a new line to test the preservation of indentation
-- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#aggregated-highlight-link-from-the-apple-iphone-user-guide)
-
-`;
+- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#epubcfi(/6/18[ch2]!/4/2/10,/4/1:19,/3:113))
+- <small>📅 Highlight taken on:: 2024-07-25 03:52:17 PM -04:00</small>
+- <small>📅 Highlight modified on:: 2024-07-25 06:51:55 PM -04:00</small>`;
 
-export const renderedCustomTemplateMock = `Title:: 📕 Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title
+export const renderedCustomTemplateMockWithDefaultSorting = `Title:: 📕 Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title
 Author:: Apple Inc.
 Genre:: Technology
 Language:: EN
-Last Read:: 2024-03-11 03:04:53 PM -04:00
+Last Read:: 2024-07-25 03:52:34 PM -04:00
 Link:: [Apple Books Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5)
 
 
 
 ## Annotations
 
-Number of annotations:: 2
+Number of annotations:: 4
 
 ----
 
-- 📖 Chapter:: Aggregated Introduction
-- 🔖 Context:: This is a contextual text for the aggregated highlight from the Apple iPhone User Guide
-- 🎯 Highlight:: <mark style="background:rgb(249,213,108); color:#000; padding:2px;">aggregated highlight from the Apple iPhone User Guide</mark>
-- 📝 Note:: Test note for the aggregated highlight from the Apple iPhone User Guide
-- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#aggregated-highlight-link-from-the-apple-iphone-user-guide)
-- <small>📅 Highlight taken on:: 2024-03-11 03:04:53 PM -04:00</small>
-- <small>📅 Highlight modified on:: 2024-03-11 03:04:53 PM -04:00</small>
+${renderedColoredAnnotationThree}
 
 ----
 
-- 📖 Chapter:: Another aggregated Introduction
-- 🔖 Context:: This is a contextual text for the aggregated highlight from the Apple iPhone User Guide
-containing a new line to test the preservation of indentation
-- 🎯 Highlight:: <mark style="background:rgb(249,213,108); color:#000; padding:2px;">aggregated highlight from the Apple iPhone User Guide
-containing a new line to test the preservation of indentation
-and another new line
-to check one more time</mark>
-- 📝 Note:: Test note for the aggregated highlight from the Apple iPhone User Guide
-along with a new line to test the preservation of indentation
-- 📙 Highlight Link:: [Apple Books Highlight Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5#aggregated-highlight-link-from-the-apple-iphone-user-guide)
-- <small>📅 Highlight taken on:: 2024-03-11 03:04:53 PM -04:00</small>
-- <small>📅 Highlight modified on:: 2024-03-11 03:04:53 PM -04:00</small>
+${renderedColoredAnnotationTwo}
+
+----
+
+${renderedColoredAnnotationFour}
+
+----
+
+${renderedColoredAnnotationOne}
 
 `;
 
@@ -75,19 +125,29 @@ Link:: [Apple Books Link](ibooks://assetid/THBFYNJKTGFTTVCGSAE5)
 
 ## Annotations
 
-Number of annotations:: 2
+Number of annotations:: 4
 
 ----
 
 > [!QUOTE]
->  aggregated highlight from the Apple iPhone User Guide
+>  third aggregated highlight from the Apple iPhone User Guide
 
 ----
 
 > [!QUOTE]
->  aggregated highlight from the Apple iPhone User Guide
+>  second aggregated highlight from the Apple iPhone User Guide
 containing a new line to test the preservation of indentation
 and another new line
 to check one more time
 
+----
+
+> [!QUOTE]
+>  fourth aggregated highlight from the Apple iPhone User Guide
+
+----
+
+> [!QUOTE]
+>  first aggregated highlight from the Apple iPhone User Guide
+
 `;
diff --git a/test/renderHighlightsTemplate.spec.ts b/test/renderHighlightsTemplate.spec.ts
index bbe0130..fea0189 100644
--- a/test/renderHighlightsTemplate.spec.ts
+++ b/test/renderHighlightsTemplate.spec.ts
@@ -4,9 +4,9 @@ import timezone from 'dayjs/plugin/timezone';
 import Handlebars from 'handlebars';
 import { describe, expect, test, vi } from 'vitest';
 import { renderHighlightsTemplate } from '../src/methods/renderHighlightsTemplate';
-import { aggregatedHighlights } from './mocks/aggregatedDetailsData';
+import { aggregatedHighlightsWithDefaultSorting } from './mocks/aggregatedDetailsData';
 import { rawCustomTemplateMock, rawCustomTemplateMockWithWrappedTextBlockContainingNewlines } from './mocks/rawTemplates';
-import { defaultTemplateMock, renderedCustomTemplateMock, renderedCustomTemplateMockWithWrappedTextBlockContainingNewlines } from './mocks/renderedTemplate';
+import { defaultTemplateMockWithAnnotationsSortedByDefault, renderedCustomTemplateMockWithDefaultSorting, renderedCustomTemplateMockWithWrappedTextBlockContainingNewlines } from './mocks/renderedTemplate';
 import defaultTemplate from '../src/template';
 import { ICombinedBooksAndHighlights } from 'src/types';
 
@@ -19,21 +19,21 @@ describe('renderHighlightsTemplate', () => {
 
 	describe('Template rendering', () => {
 		test('Should render a default template with the provided data', async () => {
-			const renderedTemplate = await renderHighlightsTemplate(aggregatedHighlights[0] as ICombinedBooksAndHighlights, defaultTemplate);
+			const renderedTemplate = await renderHighlightsTemplate(aggregatedHighlightsWithDefaultSorting[0] as ICombinedBooksAndHighlights, defaultTemplate);
 
-			expect(renderedTemplate).toEqual(defaultTemplateMock);
+			expect(renderedTemplate).toEqual(defaultTemplateMockWithAnnotationsSortedByDefault);
 		});
 
 		test('Should render a custom template with the provided data', async () => {
 			tzSpy.mockImplementation(() => 'America/New_York');
 
-			const renderedTemplate = await renderHighlightsTemplate(aggregatedHighlights[0] as ICombinedBooksAndHighlights, rawCustomTemplateMock);
+			const renderedTemplate = await renderHighlightsTemplate(aggregatedHighlightsWithDefaultSorting[0] as ICombinedBooksAndHighlights, rawCustomTemplateMock);
 
-			expect(renderedTemplate).toEqual(renderedCustomTemplateMock);
+			expect(renderedTemplate).toEqual(renderedCustomTemplateMockWithDefaultSorting);
 		});
 
 		test('Should render a custom template with the provided data and preserve newlines in wrapped text blocks', async () => {
-			const renderedTemplate = await renderHighlightsTemplate(aggregatedHighlights[0] as ICombinedBooksAndHighlights, rawCustomTemplateMockWithWrappedTextBlockContainingNewlines);
+			const renderedTemplate = await renderHighlightsTemplate(aggregatedHighlightsWithDefaultSorting[0] as ICombinedBooksAndHighlights, rawCustomTemplateMockWithWrappedTextBlockContainingNewlines);
 
 			expect(renderedTemplate).toEqual(renderedCustomTemplateMockWithWrappedTextBlockContainingNewlines);
 		});
diff --git a/test/saveHighlightsToVault.spec.ts b/test/saveHighlightsToVault.spec.ts
index 6862ce8..9e0c8d1 100644
--- a/test/saveHighlightsToVault.spec.ts
+++ b/test/saveHighlightsToVault.spec.ts
@@ -5,10 +5,10 @@ import { afterEach, beforeEach, describe, expect, test, vi } from 'vitest';
 import SaveHighlights from '../src/methods/saveHighlightsToVault';
 import { AppleBooksHighlightsImportPluginSettings } from '../src/settings';
 import { rawCustomTemplateMock, rawCustomTemplateMockWithWrappedTextBlockContainingNewlines } from './mocks/rawTemplates';
-import { aggregatedHighlights } from './mocks/aggregatedDetailsData';
+import { aggregatedUnsortedHighlights } from './mocks/aggregatedDetailsData';
 import {
-	defaultTemplateMock,
-	renderedCustomTemplateMock,
+	defaultTemplateMockWithAnnotationsSortedByDefault,
+	renderedCustomTemplateMockWithDefaultSorting,
 	renderedCustomTemplateMockWithWrappedTextBlockContainingNewlines,
 } from './mocks/renderedTemplate';
 import { ICombinedBooksAndHighlights } from '../src/types'
@@ -56,7 +56,7 @@ describe('Save highlights to vault', () => {
 		const saveHighlights = new SaveHighlights({ vault: mockVault } as any, settings);
 		const spyGetAbstractFileByPath = vi.spyOn(mockVault, 'getAbstractFileByPath').mockReturnValue('ibooks-highlights');
 
-		await saveHighlights.saveHighlightsToVault(aggregatedHighlights as ICombinedBooksAndHighlights[]);
+		await saveHighlights.saveHighlightsToVault(aggregatedUnsortedHighlights as ICombinedBooksAndHighlights[]);
 
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledTimes(1);
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledWith('ibooks-highlights');
@@ -70,7 +70,7 @@ describe('Save highlights to vault', () => {
 		expect(mockVault.create).toHaveBeenCalledTimes(1);
 		expect(mockVault.create).toHaveBeenCalledWith(
 			`ibooks-highlights/Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title.md`,
-			defaultTemplateMock
+			defaultTemplateMockWithAnnotationsSortedByDefault
 		);
 	});
 
@@ -83,7 +83,7 @@ describe('Save highlights to vault', () => {
 		const saveHighlights = new SaveHighlights({ vault: mockVault } as any, settings);
 		const spyGetAbstractFileByPath = vi.spyOn(mockVault, 'getAbstractFileByPath').mockReturnValue('ibooks-highlights');
 
-		await saveHighlights.saveHighlightsToVault(aggregatedHighlights as ICombinedBooksAndHighlights[]);
+		await saveHighlights.saveHighlightsToVault(aggregatedUnsortedHighlights as ICombinedBooksAndHighlights[]);
 
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledTimes(1);
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledWith('ibooks-highlights');
@@ -97,7 +97,7 @@ describe('Save highlights to vault', () => {
 		expect(mockVault.create).toHaveBeenCalledTimes(1);
 		expect(mockVault.create).toHaveBeenCalledWith(
 			`ibooks-highlights/Apple iPhone - User Guide - Instructions - with - restricted - symbols - in - title.md`,
-			renderedCustomTemplateMock
+			renderedCustomTemplateMockWithDefaultSorting
 		);
 	});
 
@@ -107,7 +107,7 @@ describe('Save highlights to vault', () => {
 		const saveHighlights = new SaveHighlights({ vault: mockVault } as any, settings);
 		const spyGetAbstractFileByPath = vi.spyOn(mockVault, 'getAbstractFileByPath').mockReturnValue('ibooks-highlights');
 
-		await saveHighlights.saveHighlightsToVault(aggregatedHighlights as ICombinedBooksAndHighlights[]);
+		await saveHighlights.saveHighlightsToVault(aggregatedUnsortedHighlights as ICombinedBooksAndHighlights[]);
 
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledTimes(1);
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledWith('ibooks-highlights');
@@ -130,7 +130,7 @@ describe('Save highlights to vault', () => {
 		const saveHighlights = new SaveHighlights({ vault: mockVault } as any, { ...settings, highlightsFolder: '' });
 		const spyGetAbstractFileByPath = vi.spyOn(mockVault, 'getAbstractFileByPath').mockReturnValue('');
 
-		await saveHighlights.saveHighlightsToVault(aggregatedHighlights as ICombinedBooksAndHighlights[]);
+		await saveHighlights.saveHighlightsToVault(aggregatedUnsortedHighlights as ICombinedBooksAndHighlights[]);
 
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledTimes(1);
 		expect(spyGetAbstractFileByPath).toHaveBeenCalledWith('');
@@ -156,7 +156,7 @@ describe('Save highlights to vault', () => {
 			};
 		});
 
-		await saveHighlights.saveHighlightsToVault(aggregatedHighlights as ICombinedBooksAndHighlights[]);
+		await saveHighlights.saveHighlightsToVault(aggregatedUnsortedHighlights as ICombinedBooksAndHighlights[]);
 
 		expect(spyList).toHaveBeenCalledTimes(1);
 		expect(spyList).toReturnWith({
diff --git a/test/settings.spec.ts b/test/settings.spec.ts
index d2a449e..ed2a9c7 100644
--- a/test/settings.spec.ts
+++ b/test/settings.spec.ts
@@ -16,6 +16,10 @@ describe('Plugin default settings', () => {
 		expect(settings.backup).toBeFalsy();
 	});
 
+	test("Highlights sorting criterion", () => {
+		expect(settings.highlightsSortingCriterion).toEqual('creationDateOldToNew');
+	});
+
 	test('Template', () => {
 		expect(settings.template).toEqual(defaultTemplate);
 	});
diff --git a/test/sortHighlights.spec.ts b/test/sortHighlights.spec.ts
new file mode 100644
index 0000000..42da36a
--- /dev/null
+++ b/test/sortHighlights.spec.ts
@@ -0,0 +1,179 @@
+import { describe, expect, test } from 'vitest';
+import { sortHighlights, highlightLocationToNumber, compareLocations } from '../src/methods/sortHighlights';
+import {
+	aggregatedUnsortedHighlights,
+	annotationOne,
+	annotationTwo,
+	annotationThree,
+	annotationFour
+} from './mocks/aggregatedDetailsData';
+import { ICombinedBooksAndHighlights, IHighlightsSortingCriterion} from '../src/types';
+
+describe('sortHighlights', () => {
+	describe('Highlights sorting criterion', () => {
+		test('Should sort highlights by creation date from oldest to newest', () => {
+			const highlightsSortingCriterion = IHighlightsSortingCriterion.CreationDateOldToNew;
+
+			const actual = sortHighlights(aggregatedUnsortedHighlights[0] as ICombinedBooksAndHighlights, highlightsSortingCriterion);
+
+			const expectedSortingForHighlights = {
+				...aggregatedUnsortedHighlights[0],
+				annotations: [
+					annotationThree,
+					annotationTwo,
+					annotationFour,
+					annotationOne,
+				]
+			};
+
+			expect(actual).toEqual(expectedSortingForHighlights);
+		});
+
+		test('Should sort highlights by creation date from newest to oldest', () => {
+			const highlightsSortingCriterion = IHighlightsSortingCriterion.CreationDateNewToOld;
+
+			const actual = sortHighlights(aggregatedUnsortedHighlights[0] as ICombinedBooksAndHighlights, highlightsSortingCriterion);
+
+			const expectedSortingForHighlights = {
+				...aggregatedUnsortedHighlights[0],
+				annotations: [
+					annotationOne,
+					annotationFour,
+					annotationTwo,
+					annotationThree,
+				]
+			};
+
+			expect(actual).toEqual(expectedSortingForHighlights);
+		});
+
+		test('Should sort highlights by modification date from oldest to newest', () => {
+			const highlightsSortingCriterion = IHighlightsSortingCriterion.LastModifiedDateOldToNew;
+
+			const actual = sortHighlights(aggregatedUnsortedHighlights[0] as ICombinedBooksAndHighlights, highlightsSortingCriterion);
+
+			const expectedSortingForHighlights = {
+				...aggregatedUnsortedHighlights[0],
+				annotations: [
+					annotationFour,
+					annotationOne,
+					annotationTwo,
+					annotationThree,
+				]
+			};
+
+			expect(actual).toEqual(expectedSortingForHighlights);
+		});
+
+		test('Should sort highlights by modification date from newest to oldest', () => {
+			const highlightsSortingCriterion = IHighlightsSortingCriterion.LastModifiedDateNewToOld;
+
+			const actual = sortHighlights(aggregatedUnsortedHighlights[0] as ICombinedBooksAndHighlights, highlightsSortingCriterion);
+
+			const expectedSortingForHighlights = {
+				...aggregatedUnsortedHighlights[0],
+				annotations: [
+					annotationThree,
+					annotationTwo,
+					annotationOne,
+					annotationFour,
+				]
+			};
+
+			expect(actual).toEqual(expectedSortingForHighlights);
+		});
+
+		test('Should sort highlights by location in a book', () => {
+			const highlightsSortingCriterion = IHighlightsSortingCriterion.Book;
+
+			const actual = sortHighlights(aggregatedUnsortedHighlights[0] as ICombinedBooksAndHighlights, highlightsSortingCriterion);
+
+			const expectedSortingForHighlights = {
+				...aggregatedUnsortedHighlights[0],
+				annotations: [
+					annotationOne,
+					annotationTwo,
+					annotationThree,
+					annotationFour,
+				]
+			};
+
+			expect(actual).toEqual(expectedSortingForHighlights);
+		});
+	});
+
+	describe('sortHighlights auxiliary functions', () => {
+		describe('highlightLocationToNumber', () => {
+			test('Should return the correct array of numbers from a highlight location', () => {
+				const highlightLocations = [
+					'epubcfi(/6/2[iphd3c6e37c7]!/4[iphd3c6e37c7]/6[iphefb3daa42]/6[iph22e5dfab7]/4/2/1,:0,:28)',
+					'epubcfi(/6/12[chapter1]!/4/2/16/1,:0,:87)',
+					'epubcfi(/6/12[x06_Introduction_How]!/4[x9780593422984_EPUB-4]/2/82,/1:0,/5:98)',
+					'epubcfi(/6/28[chapter-idp13097504]!/4/2/2[labeling_systems]/24/2[recap-id00006]/6/6/2/1,:0,:120)',
+					'epubcfi(/6/34[data-uuid-42e193cde5544ad5ac31696d78c19bf9]!/4/16[data-uuid-59056f0b33a144929eb7810513ae7131],/1:0,/1:292)',
+					'epubcfi(/6/34[chap10]!/4/2[chap10.html]/8/8,/2/1:0,/4/1:11)',
+					'epubcfi(/6/36[ch10]!/4/2/10,/1:19,/3:113)',
+					'epubcfi(/6/72[x9780735211308_EPUB-34]!/4[x9780735211308_EPUB-34]/2,/58/3:1,/60/1:53)',
+					'epubcfi(/6/86[chapter00191]!/4/166/1,:10,:197)',
+					'epubcfi(/6/198[ch15_sub01]!/4/2/3,:0,:96)'
+				];
+
+				const expectedNumbers = [
+					[6, 2, 4, 6, 6, 4, 2, 1, 0],
+					[6, 12, 4, 2, 16, 1, 0],
+					[6, 12, 4, 2, 82, 1, 0],
+					[6, 28, 4, 2, 2, 24, 2, 6, 6, 2, 1, 0],
+					[6, 34, 4, 16, 1, 0],
+					[6, 34, 4, 2, 8, 8, 2, 1, 0],
+					[6, 36, 4, 2, 10, 1, 19],
+					[6, 72, 4, 2, 58, 3, 1],
+					[6, 86, 4, 166, 1, 10],
+					[6, 198, 4, 2, 3, 0],
+				];
+
+				highlightLocations.forEach((highlightLocation, index) => {
+					const actual = highlightLocationToNumber(highlightLocation);
+					expect(actual).toEqual(expectedNumbers[index]);
+				});
+			});
+		});
+
+		describe('compareLocations', () => {
+			test('Should return -1 if the first location is less than the second one', () => {
+				const firstLocation = [6, 12, 4, 2, 16, 1, 0];
+				const secondLocation = [6, 12, 4, 2, 82, 1, 0];
+				const actual = compareLocations(firstLocation, secondLocation);
+				expect(actual).toBe(-1);
+			});
+
+			test('Should return 1 if the first location is greater than the second one', () => {
+				const firstLocation = [6, 12, 4, 2, 82, 1, 0];
+				const secondLocation = [6, 12, 4, 2, 16, 1, 0];
+				const actual = compareLocations(firstLocation, secondLocation);
+				expect(actual).toBe(1);
+			});
+
+			test('Should return the positive difference (+2) in lengths if the locations are equal up to the length of the shorter one (first location)', () => {
+				const firstLocation = [6, 34, 4, 16, 1, 10, 2, 0];
+				const secondLocation = [6, 34, 4, 16, 1, 10];
+				const actual = compareLocations(firstLocation, secondLocation);
+				expect(actual).toBe(2);
+			});
+
+			test('Should return the negative difference (-2) in lengths if the locations are equal up to the length of the shorter one (second location)', () => {
+				const firstLocation = [6, 34, 4, 16, 1, 10];
+				const secondLocation = [6, 34, 4, 16, 1, 10, 2, 0];
+				const actual = compareLocations(firstLocation, secondLocation);
+				expect(actual).toBe(-2);
+			});
+
+			test('Should return 0 if the locations are equal', () => {
+				const firstLocation = [6, 12, 4, 2, 16, 1, 0];
+				const secondLocation = [6, 12, 4, 2, 16, 1, 0];
+				const actual = compareLocations(firstLocation, secondLocation);
+				expect(actual).toBe(0);
+			});
+		});
+	})
+
+});