diff --git a/src/CONST.js b/src/CONST.js
index accd263483f4..30f9e24ae3e7 100755
--- a/src/CONST.js
+++ b/src/CONST.js
@@ -402,6 +402,7 @@ const CONST = {
         SHOW_LOADING_SPINNER_DEBOUNCE_TIME: 250,
         TOOLTIP_SENSE: 1000,
         TRIE_INITIALIZATION: 'trie_initialization',
+        COMMENT_LENGTH_DEBOUNCE_TIME: 500,
     },
     PRIORITY_MODE: {
         GSD: 'gsd',
diff --git a/src/components/ExceededCommentLength.js b/src/components/ExceededCommentLength.js
index 33f557c66d99..4ef6a5027e73 100644
--- a/src/components/ExceededCommentLength.js
+++ b/src/components/ExceededCommentLength.js
@@ -1,27 +1,62 @@
-import React from 'react';
+import React, {PureComponent} from 'react';
 import PropTypes from 'prop-types';
+import {debounce} from 'lodash';
 import CONST from '../CONST';
+import * as ReportUtils from '../libs/ReportUtils';
 import Text from './Text';
 import styles from '../styles/styles';
 
 const propTypes = {
-    /** The current length of the comment */
-    commentLength: PropTypes.number.isRequired,
+    /** Text Comment */
+    comment: PropTypes.string.isRequired,
+
+    /** Update UI on parent when comment length is exceeded */
+    onExceededMaxCommentLength: PropTypes.func.isRequired,
 };
 
-const ExceededCommentLength = (props) => {
-    if (props.commentLength <= CONST.MAX_COMMENT_LENGTH) {
-        return null;
+class ExceededCommentLength extends PureComponent {
+    constructor(props) {
+        super(props);
+
+        this.state = {
+            commentLength: 0,
+        };
+
+        // By debouncing, we defer the calculation until there is a break in typing
+        this.updateCommentLength = debounce(this.updateCommentLength.bind(this), CONST.TIMING.COMMENT_LENGTH_DEBOUNCE_TIME);
     }
 
-    return (
-        <Text style={[styles.textMicro, styles.textDanger, styles.chatItemComposeSecondaryRow, styles.mlAuto, styles.pl2]}>
-            {`${props.commentLength}/${CONST.MAX_COMMENT_LENGTH}`}
-        </Text>
-    );
-};
+    componentDidMount() {
+        this.updateCommentLength();
+    }
+
+    componentDidUpdate(prevProps) {
+        if (prevProps.comment === this.props.comment) {
+            return;
+        }
+
+        this.updateCommentLength();
+    }
+
+    updateCommentLength() {
+        const commentLength = ReportUtils.getCommentLength(this.props.comment);
+        this.setState({commentLength});
+        this.props.onExceededMaxCommentLength(commentLength > CONST.MAX_COMMENT_LENGTH);
+    }
+
+    render() {
+        if (this.state.commentLength <= CONST.MAX_COMMENT_LENGTH) {
+            return null;
+        }
+
+        return (
+            <Text style={[styles.textMicro, styles.textDanger, styles.chatItemComposeSecondaryRow, styles.mlAuto, styles.pl2]}>
+                {`${this.state.commentLength}/${CONST.MAX_COMMENT_LENGTH}`}
+            </Text>
+        );
+    }
+}
 
 ExceededCommentLength.propTypes = propTypes;
-ExceededCommentLength.displayName = 'ExceededCommentLength';
 
 export default ExceededCommentLength;
diff --git a/src/libs/ReportUtils.js b/src/libs/ReportUtils.js
index c824ea3e180a..c2049dd87516 100644
--- a/src/libs/ReportUtils.js
+++ b/src/libs/ReportUtils.js
@@ -774,6 +774,15 @@ function hasReportNameError(report) {
     return !_.isEmpty(lodashGet(report, 'errorFields.reportName', {}));
 }
 
+/**
+ * @param {String} text
+ * @returns {String}
+ */
+function getParsedComment(text) {
+    const parser = new ExpensiMark();
+    return text.length < CONST.MAX_MARKUP_LENGTH ? parser.replace(text) : text;
+}
+
 /**
  * @param {String} [text]
  * @param {File} [file]
@@ -783,7 +792,7 @@ function buildOptimisticAddCommentReportAction(text, file) {
     // For comments shorter than 10k chars, convert the comment from MD into HTML because that's how it is stored in the database
     // For longer comments, skip parsing and display plaintext for performance reasons. It takes over 40s to parse a 100k long string!!
     const parser = new ExpensiMark();
-    const commentText = text.length < CONST.MAX_MARKUP_LENGTH ? parser.replace(text) : text;
+    const commentText = getParsedComment(text);
     const isAttachment = _.isEmpty(text) && file !== undefined;
     const attachmentInfo = isAttachment ? file : {};
     const htmlForNewComment = isAttachment ? 'Uploading Attachment...' : commentText;
@@ -1424,13 +1433,13 @@ function getNewMarkerReportActionID(report, sortedAndFilteredReportActions) {
 }
 
 /**
- * Replace code points > 127 with C escape sequences, and return the resulting string's overall length
- * Used for compatibility with the backend auth validator for AddComment
+ * Performs the markdown conversion, and replaces code points > 127 with C escape sequences
+ * Used for compatibility with the backend auth validator for AddComment, and to account for MD in comments
  * @param {String} textComment
- * @returns {Number}
+ * @returns {Number} The comment's total length as seen from the backend
  */
 function getCommentLength(textComment) {
-    return textComment.replace(/[^ -~]/g, '\\u????').length;
+    return getParsedComment(textComment).replace(/[^ -~]/g, '\\u????').trim().length;
 }
 
 /**
diff --git a/src/pages/home/report/ReportActionCompose.js b/src/pages/home/report/ReportActionCompose.js
index 0efb256e8144..dd6d208e1123 100644
--- a/src/pages/home/report/ReportActionCompose.js
+++ b/src/pages/home/report/ReportActionCompose.js
@@ -132,6 +132,7 @@ class ReportActionCompose extends React.Component {
         this.getInputPlaceholder = this.getInputPlaceholder.bind(this);
         this.getIOUOptions = this.getIOUOptions.bind(this);
         this.addAttachment = this.addAttachment.bind(this);
+        this.setExceededMaxCommentLength = this.setExceededMaxCommentLength.bind(this);
         this.comment = props.comment;
 
         // React Native will retain focus on an input for native devices but web/mWeb behave differently so we have some focus management
@@ -153,6 +154,7 @@ class ReportActionCompose extends React.Component {
 
             // If we are on a small width device then don't show last 3 items from conciergePlaceholderOptions
             conciergePlaceholderRandomIndex: _.random(this.props.translate('reportActionCompose.conciergePlaceholderOptions').length - (this.props.isSmallScreenWidth ? 4 : 1)),
+            hasExceededMaxCommentLength: false,
         };
     }
 
@@ -302,6 +304,16 @@ class ReportActionCompose extends React.Component {
         this.setState({maxLines});
     }
 
+    /**
+     * Updates the composer when the comment length is exceeded
+     * Shows red borders and prevents the comment from being sent
+     *
+     * @param {Boolean} hasExceededMaxCommentLength
+     */
+    setExceededMaxCommentLength(hasExceededMaxCommentLength) {
+        this.setState({hasExceededMaxCommentLength});
+    }
+
     isEmptyChat() {
         return _.size(this.props.reportActions) === 1;
     }
@@ -513,8 +525,7 @@ class ReportActionCompose extends React.Component {
         const isComposeDisabled = this.props.isDrawerOpen && this.props.isSmallScreenWidth;
         const isBlockedFromConcierge = ReportUtils.chatIncludesConcierge(this.props.report) && User.isBlockedFromConcierge(this.props.blockedFromConcierge);
         const inputPlaceholder = this.getInputPlaceholder();
-        const encodedCommentLength = ReportUtils.getCommentLength(this.comment);
-        const hasExceededMaxCommentLength = encodedCommentLength > CONST.MAX_COMMENT_LENGTH;
+        const hasExceededMaxCommentLength = this.state.hasExceededMaxCommentLength;
 
         return (
             <View style={[
@@ -709,7 +720,7 @@ class ReportActionCompose extends React.Component {
                 >
                     {!this.props.isSmallScreenWidth && <OfflineIndicator containerStyles={[styles.chatItemComposeSecondaryRow]} />}
                     <ReportTypingIndicator reportID={this.props.reportID} />
-                    <ExceededCommentLength commentLength={encodedCommentLength} />
+                    <ExceededCommentLength comment={this.comment} onExceededMaxCommentLength={this.setExceededMaxCommentLength} />
                 </View>
                 {this.state.isDraggingOver && <ReportDropUI />}
             </View>
diff --git a/src/pages/home/report/ReportActionItemMessageEdit.js b/src/pages/home/report/ReportActionItemMessageEdit.js
index abef7beb65ca..37369611f190 100644
--- a/src/pages/home/report/ReportActionItemMessageEdit.js
+++ b/src/pages/home/report/ReportActionItemMessageEdit.js
@@ -69,6 +69,7 @@ class ReportActionItemMessageEdit extends React.Component {
         this.triggerSaveOrCancel = this.triggerSaveOrCancel.bind(this);
         this.onSelectionChange = this.onSelectionChange.bind(this);
         this.addEmojiToTextBox = this.addEmojiToTextBox.bind(this);
+        this.setExceededMaxCommentLength = this.setExceededMaxCommentLength.bind(this);
         this.saveButtonID = 'saveButton';
         this.cancelButtonID = 'cancelButton';
         this.emojiButtonID = 'emojiButton';
@@ -84,6 +85,7 @@ class ReportActionItemMessageEdit extends React.Component {
                 end: draftMessage.length,
             },
             isFocused: false,
+            hasExceededMaxCommentLength: false,
         };
     }
 
@@ -96,6 +98,16 @@ class ReportActionItemMessageEdit extends React.Component {
         this.setState({selection: e.nativeEvent.selection});
     }
 
+    /**
+     * Updates the composer when the comment length is exceeded
+     * Shows red borders and prevents the comment from being sent
+     *
+     * @param {Boolean} hasExceededMaxCommentLength
+     */
+    setExceededMaxCommentLength(hasExceededMaxCommentLength) {
+        this.setState({hasExceededMaxCommentLength});
+    }
+
     /**
      * Update the value of the draft in Onyx
      *
@@ -217,8 +229,7 @@ class ReportActionItemMessageEdit extends React.Component {
     }
 
     render() {
-        const draftLength = ReportUtils.getCommentLength(this.state.draft);
-        const hasExceededMaxCommentLength = draftLength > CONST.MAX_COMMENT_LENGTH;
+        const hasExceededMaxCommentLength = this.state.hasExceededMaxCommentLength;
         return (
             <View style={styles.chatItemMessage}>
                 <View
@@ -290,7 +301,7 @@ class ReportActionItemMessageEdit extends React.Component {
                         onPress={this.publishDraft}
                         text={this.props.translate('common.saveChanges')}
                     />
-                    <ExceededCommentLength commentLength={draftLength} />
+                    <ExceededCommentLength comment={this.state.draft} onExceededMaxCommentLength={this.setExceededMaxCommentLength} />
                 </View>
             </View>
         );