diff --git a/packages/ckeditor5-link/src/autolink.ts b/packages/ckeditor5-link/src/autolink.ts
index f180789d392..0ed07fae2e4 100644
--- a/packages/ckeditor5-link/src/autolink.ts
+++ b/packages/ckeditor5-link/src/autolink.ts
@@ -195,7 +195,7 @@ export default class AutoLink extends Plugin {
 
 		const watcher = new TextWatcher( editor.model, text => {
 			// 1. Detect <kbd>Space</kbd> after a text with a potential link.
-			if ( !isSingleSpaceAtTheEnd( text ) ) {
+			if ( !isSingleSpaceOrPunctuationAtTheEnd( text ) ) {
 				return;
 			}
 
@@ -335,8 +335,15 @@ export default class AutoLink extends Plugin {
 }
 
 // Check if text should be evaluated by the plugin in order to reduce number of RegExp checks on whole text.
-function isSingleSpaceAtTheEnd( text: string ): boolean {
-	return text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === ' ' && text[ text.length - 2 ] !== ' ';
+function isSingleSpaceOrPunctuationAtTheEnd( text: string ): boolean {
+	return ( text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === ' ' ||
+		text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === '. ' ||
+		text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === '! ' ||
+		text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === ': ' ||
+		text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === ', ' ||
+		text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === '; ' ||
+		text.length > MIN_LINK_LENGTH_WITH_SPACE_AT_END && text[ text.length - 1 ] === '? '
+	) && text[ text.length - 2 ] !== ' ';
 }
 
 function getUrlAtTextEnd( text: string ): string | null {
diff --git a/packages/ckeditor5-link/tests/autolink.js b/packages/ckeditor5-link/tests/autolink.js
index 963ff11811c..a6509709ebb 100644
--- a/packages/ckeditor5-link/tests/autolink.js
+++ b/packages/ckeditor5-link/tests/autolink.js
@@ -249,7 +249,7 @@ describe( 'AutoLink', () => {
 			);
 		} );
 
-		it( 'adds linkHref attribute to a text link after space', () => {
+		it( 'adds linkHref attribute to a text link after space( )', () => {
 			simulateTyping( 'https://www.cksource.com ' );
 
 			expect( getData( model ) ).to.equal(
@@ -257,6 +257,54 @@ describe( 'AutoLink', () => {
 			);
 		} );
 
+		it( 'adds linkHref attribute to a text link after period(.)', () => {
+			simulateTyping( 'https://www.cksource.com.' );
+
+			expect( getData( model ) ).to.equal(
+				'<paragraph>https://www.cksource.com.[]</paragraph>'
+			);
+		} );
+
+		it( 'adds linkHref attribute to a text link after exclamation mark(!)', () => {
+			simulateTyping( 'https://www.cksource.com!' );
+
+			expect( getData( model ) ).to.equal(
+				'<paragraph>https://www.cksource.com![]</paragraph>'
+			);
+		} );
+
+		it( 'adds linkHref attribute to a text link after colon(:)', () => {
+			simulateTyping( 'https://www.cksource.com:' );
+
+			expect( getData( model ) ).to.equal(
+				'<paragraph>https://www.cksource.com:[]</paragraph>'
+			);
+		} );
+
+		it( 'adds linkHref attribute to a text link after comma(,)', () => {
+			simulateTyping( 'https://www.cksource.com,' );
+
+			expect( getData( model ) ).to.equal(
+				'<paragraph>https://www.cksource.com,[]</paragraph>'
+			);
+		} );
+
+		it( 'adds linkHref attribute to a text link after semi-colon(;)', () => {
+			simulateTyping( 'https://www.cksource.com;' );
+
+			expect( getData( model ) ).to.equal(
+				'<paragraph>https://www.cksource.com;[]</paragraph>'
+			);
+		} );
+
+		it( 'adds linkHref attribute to a text link after question mark(?)', () => {
+			simulateTyping( 'https://www.cksource.com?' );
+
+			expect( getData( model ) ).to.equal(
+				'<paragraph>https://www.cksource.com?[]</paragraph>'
+			);
+		} );
+
 		it( 'does not add linkHref attribute if linkHref is not allowed', () => {
 			model.schema.addAttributeCheck( () => false ); // Disable all attributes.
 
diff --git a/packages/ckeditor5-link/tests/manual/autolink.md b/packages/ckeditor5-link/tests/manual/autolink.md
index dc351b52490..3c99fc610ed 100644
--- a/packages/ckeditor5-link/tests/manual/autolink.md
+++ b/packages/ckeditor5-link/tests/manual/autolink.md
@@ -10,6 +10,15 @@
 2. Type space after a URL.
 3. Check if text typed before space get converted to link.
 
+#### _Special characters_
+The process above can be completed with a set of certain special characters in place of a space:
+1. A Period (`.`)
+2. An exclamation mark (`!`)
+3. A Colon (`:`)
+4. A comma (`,`)
+5. A Semicolon (`;`)
+6. A Question mark (`?`)
+
 ### After a soft break/new paragraph
 
 1. Type a URL as in base scenario.
@@ -30,3 +39,11 @@
 2. Select some content
 3. Paste
 4. Check the selected content is now a link using the copied URL.
+
+### Ending Punctuation
+
+1. Copy a URL to the clipboard
+2. Select some content
+3. Paste
+4. Check the selected content is now a link using the copied URL.
+