diff --git a/src/EditorView.swift b/src/EditorView.swift
index 7f46982..9c9e37f 100644
--- a/src/EditorView.swift
+++ b/src/EditorView.swift
@@ -1121,37 +1121,45 @@ struct EditorTextView: NSViewRepresentable {
         func textView(_ textView: NSTextView, shouldChangeTextIn range: NSRange, replacementString text: String?) -> Bool {
             guard let text = text, text.count == 1 else { return true }
             let ch = text.first!
+            let hasSelection = range.length > 0
 
-            let closers: [Character: Character] = ["}": "{", ")": "(", "]": "["]
-            if let opener = closers[ch] {
-                let str = textView.string as NSString
-                if range.location < str.length {
-                    let next = str.character(at: range.location)
-                    if next == ch.asciiValue.map({ UInt16($0) }) ?? 0 {
-                        textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
-                        return false
+            // Skip over matching closer when cursor is right before it
+            if !hasSelection {
+                let closerChars: Set<Character> = ["}", ")", "]", "\"", "'"]
+                if closerChars.contains(ch) {
+                    let str = textView.string as NSString
+                    if range.location < str.length {
+                        let next = Character(UnicodeScalar(str.character(at: range.location))!)
+                        if next == ch {
+                            textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
+                            return false
+                        }
                     }
                 }
             }
 
-            let pairs: [Character: String] = ["{": "}", "(": ")", "[": "]"]
-            if let close = pairs[ch] {
-                textView.insertText(String(ch) + close, replacementRange: range)
-                textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
+            let pairClosers: [Character: Character] = ["{": "}", "(": ")", "[": "]"]
+            if let close = pairClosers[ch] {
+                if hasSelection {
+                    let selected = (textView.string as NSString).substring(with: range)
+                    textView.insertText(String(ch) + selected + String(close), replacementRange: range)
+                    textView.setSelectedRange(NSRange(location: range.location + 1, length: selected.count))
+                } else {
+                    textView.insertText(String(ch) + String(close), replacementRange: range)
+                    textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
+                }
                 return false
             }
 
             if ch == "\"" || ch == "'" {
-                let str = textView.string as NSString
-                if range.location < str.length {
-                    let next = str.character(at: range.location)
-                    if next == ch.asciiValue.map({ UInt16($0) }) ?? 0 {
-                        textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
-                        return false
-                    }
+                if hasSelection {
+                    let selected = (textView.string as NSString).substring(with: range)
+                    textView.insertText(String(ch) + selected + String(ch), replacementRange: range)
+                    textView.setSelectedRange(NSRange(location: range.location + 1, length: selected.count))
+                } else {
+                    textView.insertText(String(ch) + String(ch), replacementRange: range)
+                    textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
                 }
-                textView.insertText(String(ch) + String(ch), replacementRange: range)
-                textView.setSelectedRange(NSRange(location: range.location + 1, length: 0))
                 return false
             }
 
@@ -1207,17 +1215,16 @@ struct EditorTextView: NSViewRepresentable {
                     continue
                 }
 
-                let closesFirst = trimmed.hasPrefix("}") || trimmed.hasPrefix(")") || trimmed.hasPrefix("]")
-                if closesFirst && depth > 0 { depth -= 1 }
+                let opens = trimmed.filter { "{([".contains($0) }.count
+                let closes = trimmed.filter { "})]".contains($0) }.count
+                let delta = opens - closes
+
+                if delta < 0 { depth = max(0, depth + delta) }
 
                 let indent = String(repeating: "    ", count: depth)
                 result.append(indent + trimmed)
 
-                let opens = trimmed.filter { "{([".contains($0) }.count
-                let closes = trimmed.filter { "})]".contains($0) }.count
-                depth += opens - closes
-                if closesFirst { depth += 1; depth -= 1 }
-                if depth < 0 { depth = 0 }
+                if delta > 0 { depth += delta }
             }
 
             return result.joined(separator: "\n")
@@ -1244,14 +1251,13 @@ struct EditorTextView: NSViewRepresentable {
                 indent += "    "
             }
 
-            let cursorBeforeLineEnd = cursor < NSMaxRange(lineRange) - 1
             let charBeforeCursor: Character? = cursor > 0 ? Character(UnicodeScalar(str.character(at: cursor - 1))!) : nil
             let charAtCursor: Character? = cursor < str.length ? Character(UnicodeScalar(str.character(at: cursor))!) : nil
 
             // Between matching pairs: insert extra newline
             if let before = charBeforeCursor, let after = charAtCursor,
                (before == "{" && after == "}") || (before == "(" && after == ")") || (before == "[" && after == "]") {
-                let baseIndent = String(indent.dropLast(4).isEmpty ? "" : indent.dropLast(4))
+                let baseIndent = indent.count >= 4 ? String(indent.dropLast(4)) : ""
                 let insertion = "\n" + indent + "\n" + baseIndent
                 textView.insertText(insertion, replacementRange: textView.selectedRange())
                 textView.setSelectedRange(NSRange(location: cursor + 1 + indent.count, length: 0))