diff --git a/src/eepp/ui/doc/textdocument.cpp b/src/eepp/ui/doc/textdocument.cpp
index db3cbb6bd..a6649d8ee 100644
--- a/src/eepp/ui/doc/textdocument.cpp
+++ b/src/eepp/ui/doc/textdocument.cpp
@@ -2214,27 +2214,67 @@ std::vector<bool> TextDocument::autoCloseBrackets( const String& text ) {
 					continue;
 				}
 
-				if ( isClose && !isSame )
+				if ( isClose && !isSame ) {
+					mustClose = false;
+				} else if ( !isClose && !isNonWord( ch ) ) {
+					mustClose = false;
+				}
+			}
+
+			if ( mustClose && isSame ) {
+				Int64 left = sel.start().column() - 1;
+				Int64 right = sel.start().column();
+				const String& lineText = line( sel.start().line() ).getText();
+				Int64 len = lineText.size();
+				Int64 limitLeft = eemax<Int64>( 0ll, sel.start().column() - 512 );
+				Int64 limitRight = eemin<Int64>( len, sel.start().column() + 512 );
+				int unclosedQuotes = 0;
+				while ( left >= limitLeft || right < limitRight ) {
+					bool matchLeft = left >= limitLeft && lineText[left] == text[0];
+					bool matchRight = right < limitRight && lineText[right] == text[0];
+					if ( matchLeft && matchRight ) {
+						left--;
+						right++;
+					} else if ( matchLeft ) {
+						unclosedQuotes++;
+						left--;
+					} else if ( matchRight ) {
+						unclosedQuotes++;
+						right++;
+					} else {
+						if ( left >= limitLeft )
+							left--;
+						if ( right < limitRight )
+							right++;
+					}
+				}
+				if ( unclosedQuotes % 2 != 0 )
+					mustClose = false;
+			}
+
+			if ( mustClose && !isSame && !isClose ) {
+				int balance = 0;
+				int unmatchedRight = 0;
+				const String& lineText = line( sel.start().line() ).getText();
+				Int64 len = lineText.size();
+				Int64 limitLeft = eemax<Int64>( 0, sel.start().column() - 512 );
+				Int64 limitRight = eemin<Int64>( len, sel.start().column() + 512 );
+				for ( Int64 k = limitLeft; k < limitRight; ++k ) {
+					if ( lineText[k] == text[0] ) {
+						balance++;
+					} else if ( lineText[k] == closeChar ) {
+						if ( balance > 0 ) {
+							balance--;
+						} else if ( k >= sel.start().column() ) {
+							unmatchedRight++;
+						}
+					}
+				}
+				if ( unmatchedRight > 0 )
 					mustClose = false;
 			}
 
 			if ( mustClose ) {
-				/* // I'm not entirely convinced about this
-				TextPosition openStart = positionOffset( sel.start(), 1 );
-				if ( openStart != sel.start() ) {
-					int maxIt = 100;
-					while ( maxIt-- > 0 && openStart < endOfDoc() &&
-							isSpace( getChar( openStart ) ) ) {
-						openStart = nextChar( openStart );
-					}
-					if ( openStart < endOfDoc() && maxIt > 0 &&
-						 getChar( openStart ) == closeChar ) {
-						inserted.push_back( false );
-						continue;
-					}
-				}
-				*/
-
 				setSelection(
 					i, positionOffset( insert( i, sel.start(), text + String( closeChar ) ), -1 ) );
 				inserted.push_back( true );
diff --git a/src/tests/unit_tests/textdocument.cpp b/src/tests/unit_tests/textdocument.cpp
index 6e57a4281..9b77df811 100644
--- a/src/tests/unit_tests/textdocument.cpp
+++ b/src/tests/unit_tests/textdocument.cpp
@@ -113,9 +113,9 @@ UTEST( TextDocument, newLineMultiCursorAutoIndent ) {
 	doc.insert( 0, { 2, 3 }, ")" );
 
 	// Cursors between all pairs
-	doc.resetSelection( TextRanges( std::vector<TextRange>{
-		TextRange( { 0, 1 }, { 0, 1 } ), TextRange( { 1, 2 }, { 1, 2 } ),
-		TextRange( { 2, 3 }, { 2, 3 } ) } ) );
+	doc.resetSelection( TextRanges( std::vector<TextRange>{ TextRange( { 0, 1 }, { 0, 1 } ),
+															TextRange( { 1, 2 }, { 1, 2 } ),
+															TextRange( { 2, 3 }, { 2, 3 } ) } ) );
 
 	doc.newLine();
 
@@ -145,4 +145,48 @@ UTEST( TextDocument, newLineNormal ) {
 	EXPECT_STDSTREQ( TextPosition( 1, 2 ).toString(), doc.getSelection().start().toString() );
 }
 
+UTEST( TextDocument, autoCloseBrackets ) {
+	TextDocument doc;
+	doc.setAutoCloseBrackets( true );
 
+	// Test word boundary
+	doc.insert( 0, { 0, 0 }, "word" );
+	doc.setSelection( { 0, 0 } ); // Before 'word'
+	doc.textInput( "(" );		  // Next char 'w' is a word char, shouldn't auto close
+	EXPECT_STRINGEQ( "(word\n", doc.line( 0 ).getText() );
+
+	doc.reset();
+	doc.setAutoCloseBrackets( true );
+	doc.insert( 0, { 0, 0 }, " word" );
+	doc.setSelection( { 0, 0 } ); // Before ' word'
+	doc.textInput( "(" );		  // Next char ' ' is not a word char, should auto close
+	EXPECT_STRINGEQ( "() word\n", doc.line( 0 ).getText() );
+
+	doc.reset();
+	doc.setAutoCloseBrackets( true );
+	doc.insert( 0, { 0, 0 }, "() )" );
+	doc.setSelection( { 0, 1 } ); // Inside first parens
+	doc.textInput( "(" );		  // Unmatched right paren ahead, shouldn't auto close
+	EXPECT_STRINGEQ( "(() )\n", doc.line( 0 ).getText() );
+
+	doc.reset();
+	doc.setAutoCloseBrackets( true );
+	doc.insert( 0, { 0, 0 }, "()" );
+	doc.setSelection( { 0, 1 } ); // Inside first parens
+	doc.textInput( "(" );		  // Balanced right paren ahead, should auto close
+	EXPECT_STRINGEQ( "(())\n", doc.line( 0 ).getText() );
+
+	doc.reset();
+	doc.setAutoCloseBrackets( true );
+	doc.insert( 0, { 0, 0 }, "(\"\")" );
+	doc.setSelection( { 0, 2 } ); // Inside quotes
+	doc.textInput( "\"" );		  // Overwrites existing quote (stepping over)
+	EXPECT_STRINGEQ( "(\"\")\n", doc.line( 0 ).getText() );
+
+	doc.reset();
+	doc.setAutoCloseBrackets( true );
+	doc.insert( 0, { 0, 0 }, "()" );
+	doc.setSelection( { 0, 1 } ); // Inside parens
+	doc.textInput( "\"" );		  // Balanced quotes (0), should auto close
+	EXPECT_STRINGEQ( "(\"\")\n", doc.line( 0 ).getText() );
+}