diff --git a/src/muya/lib/contentState/inputCtrl.js b/src/muya/lib/contentState/inputCtrl.js
index 40b75674..e8a6c865 100644
--- a/src/muya/lib/contentState/inputCtrl.js
+++ b/src/muya/lib/contentState/inputCtrl.js
@@ -11,7 +11,21 @@ const BRACKET_HASH = {
   '*': '*',
   '_': '_',
   '"': '"',
-  '\'': '\''
+  '\'': '\'',
+  '$': '$',
+  '~': '~'
+}
+
+const BACK_HASH = {
+  '}': '{',
+  ']': '[',
+  ')': '(',
+  '*': '*',
+  '_': '_',
+  '"': '"',
+  '\'': '\'',
+  '$': '$',
+  '~': '~'
 }
 
 const inputCtrl = ContentState => {
@@ -59,28 +73,44 @@ const inputCtrl = ContentState => {
         const { autoPairBracket, autoPairMarkdownSyntax, autoPairQuote } = this
         const inputChar = text.charAt(+offset - 1)
         const preInputChar = text.charAt(+offset - 2)
+        const prePreInputChar = text.charAt(+offset - 3)
         const postInputChar = text.charAt(+offset)
-        /* eslint-disable no-useless-escape */
-        if (
+
+        if (/^delete/.test(event.inputType)) {
+          // handle `deleteContentBackward` or `deleteContentForward`
+          const deletedChar = block.text[offset]
+          if (event.inputType === 'deleteContentBackward' && postInputChar === BRACKET_HASH[deletedChar]) {
+            needRender = true
+            text = text.substring(0, offset) + text.substring(offset + 1)
+          }
+          if (event.inputType === 'deleteContentForward' && inputChar === BACK_HASH[deletedChar]) {
+            needRender = true
+            start.offset -= 1
+            end.offset -= 1
+            text = text.substring(0, offset - 1) + text.substring(offset)
+          }
+          /* eslint-disable no-useless-escape */
+        } else if (
           (event.inputType.indexOf('delete') === -1) &&
           (inputChar === postInputChar) &&
           (
             (autoPairQuote && /[']{1}/.test(inputChar)) ||
             (autoPairQuote && /["]{1}/.test(inputChar)) ||
             (autoPairBracket && /[\}\]\)]{1}/.test(inputChar)) ||
-            (autoPairMarkdownSyntax && /[*$`~_]{1}/.test(inputChar))
+            (autoPairMarkdownSyntax && /[*$`~_]{1}/.test(inputChar)) && /[_*~]{1}/.test(prePreInputChar)
           )
         ) {
+          needRender = true
           text = text.substring(0, offset) + text.substring(offset + 1)
         } else {
           /* eslint-disable no-useless-escape */
           // Not Unicode aware, since things like \p{Alphabetic} or \p{L} are not supported yet
-          const isInInlineMath = this.checkCursorInInlineMath(text, start.offset)
+          const isInInlineMath = this.checkCursorInInlineMath(text, offset)
           if (
             (autoPairQuote && /[']{1}/.test(inputChar) && !(/[a-zA-Z\d]{1}/.test(preInputChar))) ||
             (autoPairQuote && /["]{1}/.test(inputChar)) ||
             (autoPairBracket && /[\{\[\(]{1}/.test(inputChar)) ||
-            (block.functionType !== 'codeLine' && !isInInlineMath && autoPairMarkdownSyntax && /[*_]{1}/.test(inputChar))
+            (block.functionType !== 'codeLine' && !isInInlineMath && autoPairMarkdownSyntax && /[*$`~_]{1}/.test(inputChar))
           ) {
             needRender = true
             text = BRACKET_HASH[event.data]
@@ -88,8 +118,15 @@ const inputCtrl = ContentState => {
               : text
           }
           /* eslint-enable no-useless-escape */
-          if (/\s/.test(event.data) && preInputChar === '*' && postInputChar === '*') {
+          // Delete the last `*` of `**` when you insert one space between `**` to create a bullet list.
+          if (
+            /\s/.test(event.data) &&
+            /^\* /.test(text) &&
+            preInputChar === '*' &&
+            postInputChar === '*'
+            ) {
             text = text.substring(0, offset) + text.substring(offset + 1)
+            needRender = true
           }
         }
       }