diff --git a/packages/sanity/src/structure/panes/document/timeline/expandableTimelineItemMenu.tsx b/packages/sanity/src/structure/panes/document/timeline/expandableTimelineItemMenu.tsx
index 7cc5a4723cf..45139114fde 100644
--- a/packages/sanity/src/structure/panes/document/timeline/expandableTimelineItemMenu.tsx
+++ b/packages/sanity/src/structure/panes/document/timeline/expandableTimelineItemMenu.tsx
@@ -1,9 +1,38 @@
-import {Menu} from '@sanity/ui'
+import {Menu, usePortal} from '@sanity/ui'
 import {type MouseEvent, useCallback} from 'react'
 import {ContextMenuButton, useTranslation} from 'sanity'
 
 import {MenuButton, MenuItem} from '../../../../ui-components'
 import {structureLocaleNamespace} from '../../../i18n'
+import {TIMELINE_LIST_WRAPPER_ID} from './timeline'
+import {TIMELINE_MENU_PORTAL} from './timelineMenu'
+
+/**
+ * This is a hack to force the scrollbar to not appear when the list is expanding,
+ * if we don't do this the scrollbar will appear for a brief moment when the list is expanding and then disappear
+ * when the list is fully expanded.
+ */
+function hideScrollbarOnExpand(isExpanded: boolean) {
+  // Do nothing if the list is already expanded
+  if (isExpanded) return
+
+  const listWrapper = document.getElementById(TIMELINE_LIST_WRAPPER_ID)
+
+  if (listWrapper) {
+    const firstChildren = listWrapper.children[0] as HTMLElement
+    const hasScrollbar = firstChildren.scrollHeight > firstChildren.clientHeight
+    if (!hasScrollbar) {
+      //
+      const currentStyle = getComputedStyle(firstChildren).overflowY
+      // Add overflow hidden to the listWrapper to avoid the scrollbar to appear when expanding
+      firstChildren.style.overflowY = 'hidden'
+      setTimeout(() => {
+        // Reset the overflow style after the list is expanded
+        firstChildren.style.overflowY = currentStyle
+      }, 0)
+    }
+  }
+}
 
 export function ExpandableTimelineItemMenu({
   chunkId,
@@ -15,14 +44,17 @@ export function ExpandableTimelineItemMenu({
   onExpand: () => void
 }) {
   const {t} = useTranslation(structureLocaleNamespace)
+  const portalContext = usePortal()
+
   const handleExpandClick = useCallback(
     (e: MouseEvent<HTMLDivElement>) => {
-      // TODO: Avoid the click event to propagate to the parent button and closing the popover
       e.stopPropagation()
+      hideScrollbarOnExpand(isExpanded)
       onExpand()
     },
-    [onExpand],
+    [onExpand, isExpanded],
   )
+
   return (
     <MenuButton
       id={`timeline-item-menu-button-${chunkId}`}
@@ -45,6 +77,12 @@ export function ExpandableTimelineItemMenu({
           />
         </Menu>
       }
+      popover={{
+        // when used inside the timeline menu we want to keep the element inside the popover, to avoid closing the popover when clicking expand.
+        portal: portalContext.elements?.[TIMELINE_MENU_PORTAL] ? TIMELINE_MENU_PORTAL : true,
+        placement: 'bottom-end',
+        fallbackPlacements: ['left', 'left-end', 'left-start'],
+      }}
     />
   )
 }
diff --git a/packages/sanity/src/structure/panes/document/timeline/timeline.tsx b/packages/sanity/src/structure/panes/document/timeline/timeline.tsx
index edbc9d0b4a4..b7dc3e8be36 100644
--- a/packages/sanity/src/structure/panes/document/timeline/timeline.tsx
+++ b/packages/sanity/src/structure/panes/document/timeline/timeline.tsx
@@ -26,13 +26,15 @@ interface TimelineProps {
   listMaxHeight?: string
 }
 
+export const TIMELINE_LIST_WRAPPER_ID = 'timeline-list-wrapper'
+
 export const Timeline = ({
   chunks,
   hasMoreChunks,
   lastChunk: selectedChunk,
   onLoadMore,
   onSelect,
-  listMaxHeight = 'calc(100vh - 198px)',
+  listMaxHeight = 'calc(100vh - 280px)',
 }: TimelineProps) => {
   const [mounted, setMounted] = useState(false)
   const {t} = useTranslation('studio')
@@ -153,7 +155,7 @@ export const Timeline = ({
       )}
 
       {filteredChunks.length > 0 && (
-        <ListWrapper direction="column" $maxHeight={listMaxHeight}>
+        <ListWrapper direction="column" $maxHeight={listMaxHeight} id={TIMELINE_LIST_WRAPPER_ID}>
           <CommandList
             activeItemDataAttr="data-hovered"
             ariaLabel={t('timeline.list.aria-label')}
diff --git a/packages/sanity/src/structure/panes/document/timeline/timelineMenu.tsx b/packages/sanity/src/structure/panes/document/timeline/timelineMenu.tsx
index 8ea481685e5..f0268402866 100644
--- a/packages/sanity/src/structure/panes/document/timeline/timelineMenu.tsx
+++ b/packages/sanity/src/structure/panes/document/timeline/timelineMenu.tsx
@@ -2,12 +2,13 @@ import {ChevronDownIcon} from '@sanity/icons'
 import {
   Flex,
   type Placement,
+  PortalProvider,
   Text,
   useClickOutsideEvent,
   useGlobalKeyDown,
   useToast,
 } from '@sanity/ui'
-import {useCallback, useMemo, useRef, useState} from 'react'
+import {useCallback, useMemo, useState} from 'react'
 import {type Chunk, useTimelineSelector, useTranslation} from 'sanity'
 import {styled} from 'styled-components'
 
@@ -28,11 +29,14 @@ const Root = styled(Popover)`
   overflow: clip;
 `
 
+export const TIMELINE_MENU_PORTAL = 'timeline-menu'
+
 export function TimelineMenu({chunk, mode, placement}: TimelineMenuProps) {
   const {setTimelineRange, setTimelineMode, timelineError, ready, timelineStore} = useDocumentPane()
   const [open, setOpen] = useState(false)
   const [button, setButton] = useState<HTMLButtonElement | null>(null)
-  const popoverRef = useRef<HTMLDivElement | null>(null)
+  const [popoverRef, setPopoverRef] = useState<HTMLElement | null>(null)
+
   const toast = useToast()
 
   const chunks = useTimelineSelector(timelineStore, (state) => state.chunks)
@@ -64,7 +68,7 @@ export function TimelineMenu({chunk, mode, placement}: TimelineMenuProps) {
   )
 
   useGlobalKeyDown(handleGlobalKeyDown)
-  useClickOutsideEvent(open && handleClose, () => [button, popoverRef.current])
+  useClickOutsideEvent(open && handleClose, () => [button, popoverRef])
 
   const selectRev = useCallback(
     (revChunk: Chunk) => {
@@ -169,35 +173,38 @@ export function TimelineMenu({chunk, mode, placement}: TimelineMenuProps) {
   const buttonLabel = mode === 'rev' ? revLabel : sinceLabel
 
   return (
-    <Root
-      data-testid="timeline-menu"
-      constrainSize
-      content={open && content}
-      data-ui="versionMenu"
-      open={open}
-      placement={placement}
-      portal
-      ref={popoverRef}
-    >
-      <Button
-        data-testid={open ? 'timeline-menu-close-button' : 'timeline-menu-open-button'}
-        disabled={!ready}
-        mode="ghost"
-        onClick={open ? handleClose : handleOpen}
-        ref={setButton}
-        selected={open}
-        width="fill"
-        tooltipProps={null}
+    <PortalProvider __unstable_elements={{[TIMELINE_MENU_PORTAL]: popoverRef}}>
+      <Root
+        data-testid="timeline-menu"
+        constrainSize
+        content={open && content}
+        data-ui="versionMenu"
+        open={open}
+        placement={placement}
+        matchReferenceWidth
+        portal
+        ref={setPopoverRef}
       >
-        <Flex align={'center'} justify={'space-between'}>
-          <Text size={1} weight="medium">
-            {ready ? buttonLabel : t('timeline.loading-history')}
-          </Text>
-          <Text size={1}>
-            <ChevronDownIcon />
-          </Text>
-        </Flex>
-      </Button>
-    </Root>
+        <Button
+          data-testid={open ? 'timeline-menu-close-button' : 'timeline-menu-open-button'}
+          disabled={!ready}
+          mode="ghost"
+          onClick={open ? handleClose : handleOpen}
+          ref={setButton}
+          selected={open}
+          width="fill"
+          tooltipProps={null}
+        >
+          <Flex align={'center'} justify={'space-between'}>
+            <Text size={1} weight="medium">
+              {ready ? buttonLabel : t('timeline.loading-history')}
+            </Text>
+            <Text size={1}>
+              <ChevronDownIcon />
+            </Text>
+          </Flex>
+        </Button>
+      </Root>
+    </PortalProvider>
   )
 }