diff --git a/web/src/components/Changes/Changes.tsx b/web/src/components/Changes/Changes.tsx
index f7bf39941..c9ca9811d 100644
--- a/web/src/components/Changes/Changes.tsx
+++ b/web/src/components/Changes/Changes.tsx
@@ -60,6 +60,7 @@ import { InViewDiffBlockRenderer } from 'components/DiffViewer/InViewDiffBlockRe
 import Config from 'Config'
 import { PullReqSuggestionsBatch } from 'components/PullReqSuggestionsBatch/PullReqSuggestionsBatch'
 import { PullReqCustomEvent } from 'pages/PullRequest/PullRequestUtils'
+import { useCollapseHarnessNav } from 'hooks/useIsSidebarExpanded'
 import { ChangesDropdown } from './ChangesDropdown'
 import { DiffViewConfiguration } from './DiffViewConfiguration'
 import ReviewSplitButton from './ReviewSplitButton/ReviewSplitButton'
@@ -442,6 +443,7 @@ const ChangesInternal: React.FC<ChangesProps> = ({
   }, [diffs, setPullReqChangesCount])
 
   useShowRequestError(errorFileViews, 0)
+  useCollapseHarnessNav()
 
   return (
     <Container className={cx(css.container, className)} {...(!!loadingRawDiff || !!error ? { flex: true } : {})}>
diff --git a/web/src/components/CommitModalButton/CommitModalButton.module.scss b/web/src/components/CommitModalButton/CommitModalButton.module.scss
index 9161b9dc7..b17d15108 100644
--- a/web/src/components/CommitModalButton/CommitModalButton.module.scss
+++ b/web/src/components/CommitModalButton/CommitModalButton.module.scss
@@ -84,3 +84,9 @@
     }
   }
 }
+
+.formContainer {
+  form + div {
+    display: none !important;
+  }
+}
diff --git a/web/src/components/CommitModalButton/CommitModalButton.module.scss.d.ts b/web/src/components/CommitModalButton/CommitModalButton.module.scss.d.ts
index 88ee55f47..82d9d69a9 100644
--- a/web/src/components/CommitModalButton/CommitModalButton.module.scss.d.ts
+++ b/web/src/components/CommitModalButton/CommitModalButton.module.scss.d.ts
@@ -18,6 +18,7 @@
 // This is an auto-generated file
 export declare const directly: string
 export declare const extendedDescription: string
+export declare const formContainer: string
 export declare const main: string
 export declare const newBranch: string
 export declare const newBranchContainer: string
diff --git a/web/src/components/CommitModalButton/useCommitSuggestionModal.tsx b/web/src/components/CommitModalButton/useCommitSuggestionModal.tsx
index c224eac9d..0d3dd5289 100644
--- a/web/src/components/CommitModalButton/useCommitSuggestionModal.tsx
+++ b/web/src/components/CommitModalButton/useCommitSuggestionModal.tsx
@@ -89,7 +89,7 @@ export function useCommitSuggestionsModal({
             {title || getString('commitChanges')}
           </Heading>
 
-          <Container margin={{ right: 'xxlarge' }}>
+          <Container margin={{ right: 'xxlarge' }} className={css.formContainer}>
             <Formik<FormData>
               initialValues={{
                 commitMessage,
@@ -113,7 +113,7 @@ export function useCommitSuggestionsModal({
                   placeholder={extendedDescription || getString('optionalExtendedDescription')}
                 />
 
-                <Layout.Horizontal spacing="small" padding={{ right: 'xxlarge', top: 'xxlarge', bottom: 'large' }}>
+                <Layout.Horizontal spacing="small" padding={{ top: 'xxlarge', bottom: 'large' }}>
                   <Button
                     type="submit"
                     variation={ButtonVariation.PRIMARY}
diff --git a/web/src/components/DiffViewer/usePullReqComments.tsx b/web/src/components/DiffViewer/usePullReqComments.tsx
index 89632f165..a859b666e 100644
--- a/web/src/components/DiffViewer/usePullReqComments.tsx
+++ b/web/src/components/DiffViewer/usePullReqComments.tsx
@@ -35,7 +35,6 @@ import { CodeCommentStatusSelect } from 'components/CodeCommentStatusSelect/Code
 import { dispatchCustomEvent } from 'hooks/useEventListener'
 import { UseGetPullRequestInfoResult, usePullReqActivities } from 'pages/PullRequest/useGetPullRequestInfo'
 import { CommentThreadTopDecoration } from 'components/CommentThreadTopDecoration/CommentThreadTopDecoration'
-import type { SuggestionBlock } from 'components/SuggestionBlock/SuggestionBlock'
 import {
   activitiesToDiffCommentItems,
   activityToCommentItem,
@@ -288,14 +287,18 @@ export function usePullReqComments({
       // update to the latest data
       comment._commentItems = structuredClone(comment.commentItems)
 
-      const suggestionBlock: SuggestionBlock = {
-        source:
-          comment.codeBlockContent ||
-          (lineElements?.length
-            ? lineElements.map(td => td.nextElementSibling?.querySelector('.d2h-code-line-ctn')?.textContent).join('\n')
-            : lineInfo.rowElement?.lastElementChild?.querySelector('.d2h-code-line-ctn')?.textContent || ''),
-        lang: filenameToLanguage(diff.filePath.split('/').pop())
-      }
+      const suggestionBlock = comment.left
+        ? undefined
+        : {
+            source:
+              comment.codeBlockContent ||
+              (lineElements?.length
+                ? lineElements
+                    .map(td => td.nextElementSibling?.querySelector('.d2h-code-line-ctn')?.textContent)
+                    .join('\n')
+                : lineInfo.rowElement?.lastElementChild?.querySelector('.d2h-code-line-ctn')?.textContent || ''),
+            lang: filenameToLanguage(diff.filePath.split('/').pop())
+          }
 
       // Note: CommentBox is rendered as an independent React component.
       //       Everything passed to it must be either values, or refs.
diff --git a/web/src/components/MarkdownViewer/MarkdownViewer.module.scss b/web/src/components/MarkdownViewer/MarkdownViewer.module.scss
index 022215f70..895ce8747 100644
--- a/web/src/components/MarkdownViewer/MarkdownViewer.module.scss
+++ b/web/src/components/MarkdownViewer/MarkdownViewer.module.scss
@@ -75,6 +75,10 @@
   pre {
     margin-bottom: 0 !important;
     border-radius: 0 !important;
+
+    code {
+      padding: var(--spacing-small) !important;
+    }
   }
 
   .removed pre {
diff --git a/web/src/components/MarkdownViewer/MarkdownViewer.tsx b/web/src/components/MarkdownViewer/MarkdownViewer.tsx
index 4adececab..2da302cdf 100644
--- a/web/src/components/MarkdownViewer/MarkdownViewer.tsx
+++ b/web/src/components/MarkdownViewer/MarkdownViewer.tsx
@@ -17,14 +17,14 @@
 import { useHistory } from 'react-router-dom'
 import { Container, Utils } from '@harnessio/uicore'
 import rehypeSanitize from 'rehype-sanitize'
-import React, { useCallback, useEffect, useMemo, useRef, useState } from 'react'
+import React, { useCallback, useMemo, useRef, useState } from 'react'
 import { isEmpty } from 'lodash-es'
 import cx from 'classnames'
 import { getCodeString } from 'rehype-rewrite'
 import MarkdownPreview from '@uiw/react-markdown-preview'
 import rehypeVideo from 'rehype-video'
-import rehypeExternalLinks, { Element } from 'rehype-external-links'
-import { INITIAL_ZOOM_LEVEL, generateAlphaNumericHash } from 'utils/Utils'
+import rehypeExternalLinks from 'rehype-external-links'
+import { INITIAL_ZOOM_LEVEL } from 'utils/Utils'
 import ImageCarousel from 'components/ImageCarousel/ImageCarousel'
 import type { SuggestionBlock } from 'components/SuggestionBlock/SuggestionBlock'
 import { CodeSuggestionBlock } from './CodeSuggestionBlock'
@@ -32,12 +32,9 @@ import css from './MarkdownViewer.module.scss'
 
 interface MarkdownViewerProps {
   source: string
-  inDescriptionBox?: boolean
   className?: string
   maxHeight?: string | number
   darkMode?: boolean
-  handleDescUpdate?: (payload: string) => void
-  setOriginalContent?: React.Dispatch<React.SetStateAction<string>>
   suggestionBlock?: SuggestionBlock
   suggestionCheckSums?: string[]
 }
@@ -47,9 +44,6 @@ export function MarkdownViewer({
   className,
   maxHeight,
   darkMode,
-  setOriginalContent,
-  handleDescUpdate,
-  inDescriptionBox = false,
   suggestionBlock,
   suggestionCheckSums
 }: MarkdownViewerProps) {
@@ -59,7 +53,6 @@ export function MarkdownViewer({
   const [imgEvent, setImageEvent] = useState<string[]>([])
   const refRootHref = useMemo(() => document.getElementById('repository-ref-root')?.getAttribute('href'), [])
   const ref = useRef<HTMLDivElement>()
-  const [markdown, setMarkdown] = useState(source)
 
   const interceptClickEventOnViewerContainer = useCallback(
     event => {
@@ -100,42 +93,6 @@ export function MarkdownViewer({
     },
     [history]
   )
-  const [flag, setFlag] = useState(false)
-  const handleCheckboxChange = useCallback(
-    async (lineNumber: number) => {
-      const newMarkdown = source
-        .split('\n')
-        .map((line, index) => {
-          if (index === lineNumber) {
-            return line.startsWith('- [ ]') ? line.replace('- [ ]', '- [x]') : line.replace('- [x]', '- [ ]')
-          }
-          return line
-        })
-        .join('\n')
-
-      setOriginalContent?.(newMarkdown)
-      setFlag(true)
-      setMarkdown(newMarkdown)
-      handleDescUpdate?.(newMarkdown)
-    },
-    [source]
-  )
-
-  useEffect(() => {
-    const handleClick = (e: MouseEvent) => {
-      const target = e.target as HTMLInputElement
-      if (target.type === 'checkbox') {
-        const lineNumber = parseInt(target.getAttribute('data-line-number') || '0', 10)
-        handleCheckboxChange(lineNumber)
-      }
-    }
-
-    document.addEventListener('click', handleClick)
-    return () => {
-      document.removeEventListener('click', handleClick)
-    }
-  }, [source])
-  const hash = generateAlphaNumericHash(6)
 
   return (
     <Container
@@ -144,8 +101,7 @@ export function MarkdownViewer({
       style={{ maxHeight: maxHeight }}
       ref={ref}>
       <MarkdownPreview
-        key={flag ? hash : 0}
-        source={markdown}
+        source={source}
         skipHtml={false}
         warpperElement={{ 'data-color-mode': darkMode ? 'dark' : 'light' }}
         rehypeRewrite={(node, _index, parent) => {
@@ -195,16 +151,6 @@ export function MarkdownViewer({
               }
             }
           }
-          if (
-            (node as unknown as HTMLDivElement).tagName === 'input' &&
-            (node as Unknown as Element)?.properties?.type === 'checkbox'
-          ) {
-            const lineNumber = parent?.position?.start?.line ? parent?.position?.start?.line - 1 : 0
-            // eslint-disable-next-line @typescript-eslint/no-explicit-any
-            const element = node as any
-            element.properties['data-line-number'] = lineNumber.toString()
-            element.properties.disabled = !inDescriptionBox
-          }
         }}
         rehypePlugins={[
           [rehypeSanitize],
@@ -219,7 +165,7 @@ export function MarkdownViewer({
             if (
               typeof code === 'string' &&
               typeof _className === 'string' &&
-              /^language-suggestion/.test(_className.toLocaleLowerCase())
+              'language-suggestion' === _className.toLocaleLowerCase()
             ) {
               return (
                 <CodeSuggestionBlock
diff --git a/web/src/hooks/useIsSidebarExpanded.ts b/web/src/hooks/useIsSidebarExpanded.ts
index 35422d6ac..d4f37939b 100644
--- a/web/src/hooks/useIsSidebarExpanded.ts
+++ b/web/src/hooks/useIsSidebarExpanded.ts
@@ -14,8 +14,9 @@
  * limitations under the License.
  */
 
-import { useCallback, useState } from 'react'
+import { useCallback, useEffect, useRef, useState } from 'react'
 import { CustomEventName } from 'utils/Utils'
+import { useAppContext } from 'AppContext'
 import { useCustomEventListener } from './useEventListener'
 
 /**
@@ -35,3 +36,47 @@ export function useIsSidebarExpanded() {
 
   return isSidebarExpanded
 }
+
+export function useCollapseHarnessNav() {
+  const { standalone } = useAppContext()
+  const isSidebarExpanded = useIsSidebarExpanded()
+  const handled = useRef(!standalone && isSidebarExpanded)
+  const internalFlags = useRef({
+    initialized: false
+  })
+
+  useEffect(() => {
+    if (handled.current) {
+      const nav = document.getElementById('main-side-nav')
+      const pullReqNavItem = nav?.querySelector('[data-code-repo-section="pull-requests"]')
+      const toggleNavButton = nav?.querySelector('span[icon][class*="SideNavToggleButton"]') as HTMLElement
+
+      if (pullReqNavItem && toggleNavButton) {
+        const isCollapsed = pullReqNavItem.clientWidth <= 64
+
+        if (!isCollapsed) {
+          setTimeout(() => {
+            toggleNavButton.click()
+            internalFlags.current.initialized = true
+          }, 0)
+        }
+      }
+
+      return () => {
+        if (handled.current) {
+          toggleNavButton.click()
+        }
+      }
+    }
+  }, [])
+
+  useEffect(() => {
+    if (internalFlags.current.initialized && !isSidebarExpanded) {
+      internalFlags.current.initialized = false
+
+      if (handled.current) {
+        handled.current = false
+      }
+    }
+  }, [isSidebarExpanded])
+}
diff --git a/web/src/pages/PullRequest/Conversation/Conversation.module.scss b/web/src/pages/PullRequest/Conversation/Conversation.module.scss
index 06c62d107..9b55ff274 100644
--- a/web/src/pages/PullRequest/Conversation/Conversation.module.scss
+++ b/web/src/pages/PullRequest/Conversation/Conversation.module.scss
@@ -34,6 +34,13 @@
         display: inline-block;
       }
     }
+
+    :global {
+      .task-list-item,
+      .task-list-item input {
+        cursor: pointer;
+      }
+    }
   }
 }
 
diff --git a/web/src/pages/PullRequest/Conversation/Conversation.tsx b/web/src/pages/PullRequest/Conversation/Conversation.tsx
index 43c9c2812..1cd263017 100644
--- a/web/src/pages/PullRequest/Conversation/Conversation.tsx
+++ b/web/src/pages/PullRequest/Conversation/Conversation.tsx
@@ -265,10 +265,13 @@ export const Conversation: React.FC<ConversationProps> = ({
         const comment = activitiesToDiffCommentItems(activity?.code_comment?.path as string, [
           activity as TypesPullReqActivity
         ])[0]
-        const suggestionBlock = {
-          source: comment.codeBlockContent as string,
-          lang: filenameToLanguage(activity?.code_comment?.path?.split('/').pop())
-        }
+
+        const suggestionBlock = comment.left
+          ? undefined
+          : {
+              source: comment.codeBlockContent as string,
+              lang: filenameToLanguage(activity?.code_comment?.path?.split('/').pop())
+            }
 
         return (
           <ThreadSection
diff --git a/web/src/pages/PullRequest/Conversation/DescriptionBox.tsx b/web/src/pages/PullRequest/Conversation/DescriptionBox.tsx
index 1b79045cf..dc43028f4 100644
--- a/web/src/pages/PullRequest/Conversation/DescriptionBox.tsx
+++ b/web/src/pages/PullRequest/Conversation/DescriptionBox.tsx
@@ -14,7 +14,7 @@
  * limitations under the License.
  */
 
-import React, { useCallback, useEffect, useState } from 'react'
+import React, { useCallback, useEffect, useRef, useState } from 'react'
 import { Button, ButtonSize, ButtonVariation, Container, Layout, useToaster, Text } from '@harnessio/uicore'
 import cx from 'classnames'
 import { useParams } from 'react-router-dom'
@@ -80,18 +80,78 @@ export const DescriptionBox: React.FC<DescriptionBoxProps> = ({
     setFlag(true)
   }, [])
 
-  const handleDescUpdate = useCallback((markdown: string) => {
-    const payload: OpenapiUpdatePullReqRequest = {
-      title: pullReqMetadata.title,
-      description: markdown || ''
-    }
-    setOriginalContent(markdown)
-    mutate(payload)
-      .then(() => {
-        setContent(markdown)
-      })
-      .catch(exception => showError(getErrorMessage(exception), 0, getString('pr.failedToUpdate')))
-  }, [])
+  const handleDescUpdate = useCallback(
+    (markdown: string) => {
+      const payload: OpenapiUpdatePullReqRequest = {
+        title: pullReqMetadata.title,
+        description: markdown || ''
+      }
+      setOriginalContent(markdown)
+      mutate(payload)
+        .then(() => {
+          setContent(markdown)
+        })
+        .catch(exception => showError(getErrorMessage(exception), 0, getString('pr.failedToUpdate')))
+    },
+    [getString, mutate, pullReqMetadata.title, showError]
+  )
+
+  const viewerDOMRef = useRef<HTMLElement>()
+
+  useEffect(
+    function toggleTodoCheck() {
+      const dom = viewerDOMRef.current
+      const TODO_LIST_MARKER = 'data-todo-index'
+      const TODO_LIST_ITEM_CLASS = 'task-list-item'
+
+      if (dom && !edit) {
+        const handleClick = (e: MouseEvent) => {
+          const targetIsListItem = (e.target as HTMLElement).classList.contains(TODO_LIST_ITEM_CLASS)
+          const target = (e.target as HTMLElement)?.closest?.(`.${TODO_LIST_ITEM_CLASS}`)
+          const input = target?.firstElementChild as HTMLInputElement
+          const checked = targetIsListItem ? !input?.checked : input?.checked
+          let sourceIndex = -1
+
+          if (!input) return
+
+          const index = Number(target?.getAttribute(TODO_LIST_MARKER))
+
+          const newContent = originalContent
+            .split('\n')
+            .map(line => {
+              if (line.startsWith('- [ ]') || line.startsWith('- [x]')) {
+                sourceIndex++
+
+                if (index === sourceIndex) {
+                  return checked ? line.replace('- [ ]', '- [x]') : line.replace('- [x]', '- [ ]')
+                }
+              }
+              return line
+            })
+            .join('\n')
+
+          setContent(newContent)
+          setOriginalContent(newContent)
+
+          e.preventDefault()
+          e.stopPropagation()
+
+          handleDescUpdate(newContent)
+        }
+
+        // Enable all check inputs to allow clicking
+        dom.querySelectorAll(`.${TODO_LIST_ITEM_CLASS} input`)?.forEach((input, index) => {
+          input.removeAttribute('disabled')
+          input.parentElement?.setAttribute(TODO_LIST_MARKER, String(index))
+        })
+
+        dom.addEventListener('click', handleClick)
+
+        return () => dom.removeEventListener('click', handleClick)
+      }
+    },
+    [edit, handleDescUpdate, originalContent]
+  )
 
   return (
     <Container className={cx({ [css.box]: !edit, [css.desc]: !edit })}>
@@ -184,31 +244,28 @@ export const DescriptionBox: React.FC<DescriptionBoxProps> = ({
             autoFocusAndPosition={true}
           />
         )) || (
-          <Container className={css.mdWrapper}>
-            <MarkdownViewer
-              inDescriptionBox={true}
-              setOriginalContent={setOriginalContent}
-              source={content}
-              handleDescUpdate={handleDescUpdate}
-            />
-            <Container className={css.menuWrapper}>
-              <OptionsMenuButton
-                isDark={true}
-                icon="Options"
-                iconProps={{ size: 14 }}
-                style={{ padding: '5px' }}
-                items={[
-                  {
-                    text: getString('edit'),
-                    className: css.optionMenuIcon,
-                    hasIcon: true,
-                    iconName: 'Edit',
-                    onClick: () => setEdit(true)
-                  }
-                ]}
-              />
+          <React.Fragment key={originalContent}>
+            <Container className={css.mdWrapper} ref={viewerDOMRef}>
+              <MarkdownViewer source={content} />
+              <Container className={css.menuWrapper}>
+                <OptionsMenuButton
+                  isDark={true}
+                  icon="Options"
+                  iconProps={{ size: 14 }}
+                  style={{ padding: '5px' }}
+                  items={[
+                    {
+                      text: getString('edit'),
+                      className: css.optionMenuIcon,
+                      hasIcon: true,
+                      iconName: 'Edit',
+                      onClick: () => setEdit(true)
+                    }
+                  ]}
+                />
+              </Container>
             </Container>
-          </Container>
+          </React.Fragment>
         )}
       </Container>
       <NavigationCheck when={dirty} />