diff --git a/apps/sim/app/workspace/[workspaceId]/home/components/mothership-chat/mothership-chat.tsx b/apps/sim/app/workspace/[workspaceId]/home/components/mothership-chat/mothership-chat.tsx
index fb94ac5a759..b477c4744e4 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/components/mothership-chat/mothership-chat.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/home/components/mothership-chat/mothership-chat.tsx
@@ -10,7 +10,10 @@ import {
 } from '@/app/workspace/[workspaceId]/home/components/message-content'
 import { PendingTagIndicator } from '@/app/workspace/[workspaceId]/home/components/message-content/components/special-tags'
 import { QueuedMessages } from '@/app/workspace/[workspaceId]/home/components/queued-messages'
-import { UserInput } from '@/app/workspace/[workspaceId]/home/components/user-input'
+import {
+  UserInput,
+  type UserInputHandle,
+} from '@/app/workspace/[workspaceId]/home/components/user-input'
 import { UserMessageContent } from '@/app/workspace/[workspaceId]/home/components/user-message-content'
 import type {
   ChatMessage,
@@ -36,14 +39,12 @@ interface MothershipChatProps {
   messageQueue: QueuedMessage[]
   onRemoveQueuedMessage: (id: string) => void
   onSendQueuedMessage: (id: string) => Promise<void>
-  onEditQueuedMessage: (id: string) => void
+  onEditQueuedMessage: (id: string) => QueuedMessage | undefined
   userId?: string
   chatId?: string
   onContextAdd?: (context: ChatContext) => void
   onContextRemove?: (context: ChatContext) => void
   onWorkspaceResourceSelect?: (resource: MothershipResource) => void
-  editValue?: string
-  onEditValueConsumed?: () => void
   layout?: 'mothership-view' | 'copilot-view'
   initialScrollBlocked?: boolean
   animateInput?: boolean
@@ -91,8 +92,6 @@ export function MothershipChat({
   onContextAdd,
   onContextRemove,
   onWorkspaceResourceSelect,
-  editValue,
-  onEditValueConsumed,
   layout = 'mothership-view',
   initialScrollBlocked = false,
   animateInput = false,
@@ -106,11 +105,24 @@ export function MothershipChat({
   })
   const hasMessages = messages.length > 0
   const initialScrollDoneRef = useRef(false)
+  const userInputRef = useRef<UserInputHandle>(null)
   const handleSendQueuedHead = useCallback(() => {
     const topMessage = messageQueue[0]
     if (!topMessage) return
     void onSendQueuedMessage(topMessage.id)
   }, [messageQueue, onSendQueuedMessage])
+  const handleEditQueued = useCallback(
+    (id: string) => {
+      const msg = onEditQueuedMessage(id)
+      if (msg) userInputRef.current?.loadQueuedMessage(msg)
+    },
+    [onEditQueuedMessage]
+  )
+  const handleEditQueuedTail = useCallback(() => {
+    const tail = messageQueue[messageQueue.length - 1]
+    if (!tail) return
+    handleEditQueued(tail.id)
+  }, [messageQueue, handleEditQueued])
 
   useLayoutEffect(() => {
     if (!hasMessages) {
@@ -205,9 +217,10 @@ export function MothershipChat({
             messageQueue={messageQueue}
             onRemove={onRemoveQueuedMessage}
             onSendNow={onSendQueuedMessage}
-            onEdit={onEditQueuedMessage}
+            onEdit={handleEditQueued}
           />
           <UserInput
+            ref={userInputRef}
             onSubmit={onSubmit}
             isSending={isStreamActive}
             onStopGeneration={onStopGeneration}
@@ -215,9 +228,8 @@ export function MothershipChat({
             userId={userId}
             onContextAdd={onContextAdd}
             onContextRemove={onContextRemove}
-            editValue={editValue}
-            onEditValueConsumed={onEditValueConsumed}
             onSendQueuedHead={handleSendQueuedHead}
+            onEditQueuedTail={handleEditQueuedTail}
           />
         </div>
       </div>
diff --git a/apps/sim/app/workspace/[workspaceId]/home/components/queued-messages/queued-messages.tsx b/apps/sim/app/workspace/[workspaceId]/home/components/queued-messages/queued-messages.tsx
index c883cd49f25..55c0478727b 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/components/queued-messages/queued-messages.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/home/components/queued-messages/queued-messages.tsx
@@ -1,10 +1,13 @@
 'use client'
 
-import { useState } from 'react'
-import { ArrowUp, ChevronDown, ChevronRight, Pencil, Trash2 } from 'lucide-react'
+import { useEffect, useRef, useState } from 'react'
+import { ArrowUp, ChevronDown, ChevronRight, Paperclip, Pencil, Trash2 } from 'lucide-react'
 import { Tooltip } from '@/components/emcn'
+import { UserMessageContent } from '@/app/workspace/[workspaceId]/home/components/user-message-content'
 import type { QueuedMessage } from '@/app/workspace/[workspaceId]/home/types'
 
+const NARROW_WIDTH_PX = 320
+
 interface QueuedMessagesProps {
   messageQueue: QueuedMessage[]
   onRemove: (id: string) => void
@@ -14,11 +17,28 @@ interface QueuedMessagesProps {
 
 export function QueuedMessages({ messageQueue, onRemove, onSendNow, onEdit }: QueuedMessagesProps) {
   const [isExpanded, setIsExpanded] = useState(true)
+  const containerRef = useRef<HTMLDivElement>(null)
+  const [isNarrow, setIsNarrow] = useState(false)
+
+  const hasMessages = messageQueue.length > 0
 
-  if (messageQueue.length === 0) return null
+  useEffect(() => {
+    const el = containerRef.current
+    if (!el) return
+    const ro = new ResizeObserver((entries) => {
+      setIsNarrow(entries[0].contentRect.width < NARROW_WIDTH_PX)
+    })
+    ro.observe(el)
+    return () => ro.disconnect()
+  }, [hasMessages])
+
+  if (!hasMessages) return null
 
   return (
-    <div className='-mb-3 mx-3.5 overflow-hidden rounded-t-[16px] border border-[var(--border-1)] border-b-0 bg-[var(--surface-3)] pb-3'>
+    <div
+      ref={containerRef}
+      className='-mb-3 mx-3.5 overflow-hidden rounded-t-[16px] border border-[var(--border-1)] border-b-0 bg-[var(--surface-3)] pb-3'
+    >
       <button
         type='button'
         onClick={() => setIsExpanded(!isExpanded)}
@@ -39,16 +59,41 @@ export function QueuedMessages({ messageQueue, onRemove, onSendNow, onEdit }: Qu
           {messageQueue.map((msg) => (
             <div
               key={msg.id}
-              className='flex items-center gap-2 px-3.5 py-1.5 transition-colors hover-hover:bg-[var(--surface-active)]'
+              className='flex items-center gap-2 py-1.5 pr-2 pl-3.5 transition-colors hover-hover:bg-[var(--surface-active)]'
             >
               <div className='flex h-[16px] w-[16px] shrink-0 items-center justify-center'>
                 <div className='h-[10px] w-[10px] rounded-full border-[1.5px] border-[color-mix(in_srgb,var(--text-tertiary)_40%,transparent)]' />
               </div>
 
-              <div className='min-w-0 flex-1'>
-                <p className='truncate text-[var(--text-primary)] text-small'>{msg.content}</p>
+              <div className='min-w-0 flex-1 overflow-hidden'>
+                <UserMessageContent
+                  content={msg.content}
+                  contexts={msg.contexts}
+                  plainMentions
+                  className='!truncate !whitespace-nowrap !text-small !leading-[20px]'
+                />
               </div>
 
+              {msg.fileAttachments && msg.fileAttachments.length > 0 && (
+                <span className='inline-flex min-w-0 max-w-[40%] shrink items-center gap-1 rounded-[5px] bg-[var(--surface-5)] px-[5px] py-0.5 text-[var(--text-primary)] text-small'>
+                  <Paperclip className='h-[12px] w-[12px] shrink-0 text-[var(--text-icon)]' />
+                  {isNarrow ? (
+                    <span className='shrink-0 text-[var(--text-secondary)]'>
+                      {msg.fileAttachments.length}
+                    </span>
+                  ) : (
+                    <>
+                      <span className='truncate'>{msg.fileAttachments[0].filename}</span>
+                      {msg.fileAttachments.length > 1 && (
+                        <span className='shrink-0 text-[var(--text-secondary)]'>
+                          +{msg.fileAttachments.length - 1}
+                        </span>
+                      )}
+                    </>
+                  )}
+                </span>
+              )}
+
               <div className='flex shrink-0 items-center gap-0.5'>
                 <Tooltip.Root>
                   <Tooltip.Trigger asChild>
diff --git a/apps/sim/app/workspace/[workspaceId]/home/components/user-input/index.ts b/apps/sim/app/workspace/[workspaceId]/home/components/user-input/index.ts
index bcfb231f9ab..7570eb16edc 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/components/user-input/index.ts
+++ b/apps/sim/app/workspace/[workspaceId]/home/components/user-input/index.ts
@@ -1 +1 @@
-export { UserInput } from './user-input'
+export { UserInput, type UserInputHandle } from './user-input'
diff --git a/apps/sim/app/workspace/[workspaceId]/home/components/user-input/user-input.tsx b/apps/sim/app/workspace/[workspaceId]/home/components/user-input/user-input.tsx
index bae0f084183..a243e39055c 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/components/user-input/user-input.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/home/components/user-input/user-input.tsx
@@ -1,7 +1,16 @@
 'use client'
 
 import type React from 'react'
-import { useCallback, useEffect, useLayoutEffect, useMemo, useRef, useState } from 'react'
+import {
+  forwardRef,
+  useCallback,
+  useEffect,
+  useImperativeHandle,
+  useLayoutEffect,
+  useMemo,
+  useRef,
+  useState,
+} from 'react'
 import { useParams } from 'next/navigation'
 import { useSession } from '@/lib/auth/auth-client'
 import { SIM_RESOURCE_DRAG_TYPE, SIM_RESOURCES_DRAG_TYPE } from '@/lib/copilot/resource-types'
@@ -26,6 +35,7 @@ import {
 import type {
   FileAttachmentForApi,
   MothershipResource,
+  QueuedMessage,
 } from '@/app/workspace/[workspaceId]/home/types'
 import {
   useContextManagement,
@@ -91,8 +101,6 @@ function getCaretAnchor(
 
 interface UserInputProps {
   defaultValue?: string
-  editValue?: string
-  onEditValueConsumed?: () => void
   onSubmit: (
     text: string,
     fileAttachments?: FileAttachmentForApi[],
@@ -105,21 +113,28 @@ interface UserInputProps {
   onContextAdd?: (context: ChatContext) => void
   onContextRemove?: (context: ChatContext) => void
   onSendQueuedHead?: () => void
+  onEditQueuedTail?: () => void
+}
+
+export interface UserInputHandle {
+  loadQueuedMessage: (msg: QueuedMessage) => void
 }
 
-export function UserInput({
-  defaultValue = '',
-  editValue,
-  onEditValueConsumed,
-  onSubmit,
-  isSending,
-  onStopGeneration,
-  isInitialView = true,
-  userId,
-  onContextAdd,
-  onContextRemove,
-  onSendQueuedHead,
-}: UserInputProps) {
+export const UserInput = forwardRef<UserInputHandle, UserInputProps>(function UserInput(
+  {
+    defaultValue = '',
+    onSubmit,
+    isSending,
+    onStopGeneration,
+    isInitialView = true,
+    userId,
+    onContextAdd,
+    onContextRemove,
+    onSendQueuedHead,
+    onEditQueuedTail,
+  },
+  ref
+) {
   const { workspaceId } = useParams<{ workspaceId: string }>()
   const { navigateToSettings } = useSettingsNavigation()
   const { data: workflowsById = {} } = useWorkflowMap(workspaceId)
@@ -136,18 +151,6 @@ export function UserInput({
     setPrevDefaultValue(defaultValue)
   }
 
-  const [prevEditValue, setPrevEditValue] = useState(editValue)
-  if (editValue && editValue !== prevEditValue) {
-    setPrevEditValue(editValue)
-    setValue(editValue)
-  } else if (!editValue && prevEditValue) {
-    setPrevEditValue(editValue)
-  }
-
-  useEffect(() => {
-    if (editValue) onEditValueConsumed?.()
-  }, [editValue, onEditValueConsumed])
-
   const files = useFileAttachments({
     userId: userId || session?.user?.id,
     workspaceId,
@@ -269,6 +272,8 @@ export function UserInput({
   contextRef.current = contextManagement
   const onSendQueuedHeadRef = useRef(onSendQueuedHead)
   onSendQueuedHeadRef.current = onSendQueuedHead
+  const onEditQueuedTailRef = useRef(onEditQueuedTail)
+  onEditQueuedTailRef.current = onEditQueuedTail
   const isSendingRef = useRef(isSending)
   isSendingRef.current = isSending
 
@@ -277,6 +282,34 @@ export function UserInput({
   const atInsertPosRef = useRef<number | null>(null)
   const pendingCursorRef = useRef<number | null>(null)
 
+  useImperativeHandle(
+    ref,
+    () => ({
+      loadQueuedMessage: (msg: QueuedMessage) => {
+        setValue(msg.content)
+        const restored: AttachedFile[] = (msg.fileAttachments ?? []).map((a) => ({
+          id: a.id,
+          name: a.filename,
+          size: a.size,
+          type: a.media_type,
+          path: a.path ?? '',
+          key: a.key,
+          uploading: false,
+        }))
+        files.restoreAttachedFiles(restored)
+        contextManagement.setSelectedContexts(msg.contexts ?? [])
+        requestAnimationFrame(() => {
+          const textarea = textareaRef.current
+          if (!textarea) return
+          textarea.focus()
+          const end = textarea.value.length
+          textarea.setSelectionRange(end, end)
+        })
+      },
+    }),
+    [files.restoreAttachedFiles, contextManagement.setSelectedContexts, textareaRef]
+  )
+
   useLayoutEffect(() => {
     const textarea = textareaRef.current
     if (!textarea) return
@@ -430,6 +463,7 @@ export function UserInput({
         filename: f.name,
         media_type: f.type,
         size: f.size,
+        ...(f.path ? { path: f.path } : {}),
       }))
 
     onSubmit(
@@ -452,6 +486,15 @@ export function UserInput({
 
   const handleKeyDown = useCallback(
     (e: React.KeyboardEvent<HTMLTextAreaElement>) => {
+      if (e.key === 'ArrowUp' && !e.shiftKey && !e.metaKey && !e.ctrlKey && !e.altKey) {
+        const isEmpty = valueRef.current.length === 0 && filesRef.current.attachedFiles.length === 0
+        if (isEmpty && onEditQueuedTailRef.current) {
+          e.preventDefault()
+          onEditQueuedTailRef.current()
+          return
+        }
+      }
+
       if (e.key === 'Enter' && !e.shiftKey && !e.nativeEvent.isComposing) {
         e.preventDefault()
         const hasSubmitPayload =
@@ -763,4 +806,4 @@ export function UserInput({
       {files.isDragging && <DropOverlay />}
     </div>
   )
-}
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/home/components/user-message-content/user-message-content.tsx b/apps/sim/app/workspace/[workspaceId]/home/components/user-message-content/user-message-content.tsx
index d4a3ea7c7c1..bbba6b4bd72 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/components/user-message-content/user-message-content.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/home/components/user-message-content/user-message-content.tsx
@@ -2,6 +2,7 @@
 
 import { useMemo } from 'react'
 import { useParams } from 'next/navigation'
+import { cn } from '@/lib/core/utils/cn'
 import { ContextMentionIcon } from '@/app/workspace/[workspaceId]/home/components/context-mention-icon'
 import type { ChatMessageContext } from '@/app/workspace/[workspaceId]/home/types'
 import { useWorkflows } from '@/hooks/queries/workflows'
@@ -12,6 +13,9 @@ const USER_MESSAGE_CLASSES =
 interface UserMessageContentProps {
   content: string
   contexts?: ChatMessageContext[]
+  className?: string
+  /** When true, render mentions as plain inline text (no icon/pill) so truncation flows naturally. */
+  plainMentions?: boolean
 }
 
 function escapeRegex(str: string): string {
@@ -64,17 +68,23 @@ function MentionHighlight({ context }: { context: ChatMessageContext }) {
   )
 }
 
-export function UserMessageContent({ content, contexts }: UserMessageContentProps) {
+export function UserMessageContent({
+  content,
+  contexts,
+  className,
+  plainMentions = false,
+}: UserMessageContentProps) {
   const trimmed = content.trim()
+  const classes = cn(USER_MESSAGE_CLASSES, className)
 
   if (!contexts || contexts.length === 0) {
-    return <p className={USER_MESSAGE_CLASSES}>{trimmed}</p>
+    return <p className={classes}>{trimmed}</p>
   }
 
   const ranges = computeMentionRanges(content, contexts)
 
   if (ranges.length === 0) {
-    return <p className={USER_MESSAGE_CLASSES}>{trimmed}</p>
+    return <p className={classes}>{trimmed}</p>
   }
 
   const elements: React.ReactNode[] = []
@@ -88,7 +98,20 @@ export function UserMessageContent({ content, contexts }: UserMessageContentProp
       elements.push(<span key={`text-${i}-${lastIndex}`}>{before}</span>)
     }
 
-    elements.push(<MentionHighlight key={`mention-${i}-${range.start}`} context={range.context} />)
+    if (plainMentions) {
+      elements.push(
+        <span
+          key={`mention-${i}-${range.start}`}
+          className='font-medium text-[var(--text-primary)]'
+        >
+          {content.slice(range.start, range.end)}
+        </span>
+      )
+    } else {
+      elements.push(
+        <MentionHighlight key={`mention-${i}-${range.start}`} context={range.context} />
+      )
+    }
     lastIndex = range.end
   }
 
@@ -97,5 +120,5 @@ export function UserMessageContent({ content, contexts }: UserMessageContentProp
     elements.push(<span key={`tail-${lastIndex}`}>{tail}</span>)
   }
 
-  return <p className={USER_MESSAGE_CLASSES}>{elements}</p>
+  return <p className={classes}>{elements}</p>
 }
diff --git a/apps/sim/app/workspace/[workspaceId]/home/home.tsx b/apps/sim/app/workspace/[workspaceId]/home/home.tsx
index 1687a1973d1..5680f8efdd9 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/home.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/home/home.tsx
@@ -159,26 +159,6 @@ export function Home({ chatId }: HomeProps = {}) {
     })
   )
 
-  const [editingInputValue, setEditingInputValue] = useState('')
-  const [prevChatId, setPrevChatId] = useState(chatId)
-  const clearEditingValue = useCallback(() => setEditingInputValue(''), [])
-
-  // Clear editing value when navigating to a different chat (guarded render-phase update)
-  if (chatId !== prevChatId) {
-    setPrevChatId(chatId)
-    setEditingInputValue('')
-  }
-
-  const handleEditQueuedMessage = useCallback(
-    (id: string) => {
-      const msg = editQueuedMessage(id)
-      if (msg) {
-        setEditingInputValue(msg.content)
-      }
-    },
-    [editQueuedMessage]
-  )
-
   useEffect(() => {
     const url = new URL(window.location.href)
     if (activeResourceId) {
@@ -375,13 +355,11 @@ export function Home({ chatId }: HomeProps = {}) {
           messageQueue={messageQueue}
           onRemoveQueuedMessage={removeFromQueue}
           onSendQueuedMessage={sendNow}
-          onEditQueuedMessage={handleEditQueuedMessage}
+          onEditQueuedMessage={editQueuedMessage}
           userId={session?.user?.id}
           chatId={resolvedChatId}
           onContextAdd={handleContextAdd}
           onWorkspaceResourceSelect={handleWorkspaceResourceSelect}
-          editValue={editingInputValue}
-          onEditValueConsumed={clearEditingValue}
           animateInput={isInputEntering}
           onInputAnimationEnd={isInputEntering ? () => setIsInputEntering(false) : undefined}
           initialScrollBlocked={resources.length > 0 && isResourceCollapsed}
diff --git a/apps/sim/app/workspace/[workspaceId]/home/types.ts b/apps/sim/app/workspace/[workspaceId]/home/types.ts
index ce1ef99b203..d41ea9e3d36 100644
--- a/apps/sim/app/workspace/[workspaceId]/home/types.ts
+++ b/apps/sim/app/workspace/[workspaceId]/home/types.ts
@@ -46,6 +46,7 @@ export interface FileAttachmentForApi {
   filename: string
   media_type: string
   size: number
+  path?: string
 }
 
 export interface QueuedMessage {
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/copilot/components/user-input/hooks/use-file-attachments.ts b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/copilot/components/user-input/hooks/use-file-attachments.ts
index 7bf0f2079b5..f449413794e 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/copilot/components/user-input/hooks/use-file-attachments.ts
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/copilot/components/user-input/hooks/use-file-attachments.ts
@@ -301,6 +301,19 @@ export function useFileAttachments(props: UseFileAttachmentsProps) {
     setAttachedFiles([])
   }, [attachedFiles])
 
+  /**
+   * Replaces the current attached files with a given set.
+   * Cleans up preview URLs from the prior set before replacing.
+   */
+  const restoreAttachedFiles = useCallback((files: AttachedFile[]) => {
+    setAttachedFiles((prev) => {
+      prev.forEach((f) => {
+        if (f.previewUrl) URL.revokeObjectURL(f.previewUrl)
+      })
+      return files
+    })
+  }, [])
+
   return {
     // State
     attachedFiles,
@@ -321,6 +334,7 @@ export function useFileAttachments(props: UseFileAttachmentsProps) {
     handleDragOver,
     handleDrop,
     clearAttachedFiles,
+    restoreAttachedFiles,
     processFiles,
   }
 }
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx
index 8c9fe1ae87d..e881ed300dd 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/panel.tsx
@@ -392,17 +392,6 @@ export const Panel = memo(function Panel({ workspaceId: propWorkspaceId }: Panel
     wasCopilotSendingRef.current = copilotIsSending
   }, [copilotIsSending, loadCopilotChats])
 
-  const [copilotEditingInputValue, setCopilotEditingInputValue] = useState('')
-  const clearCopilotEditingValue = useCallback(() => setCopilotEditingInputValue(''), [])
-
-  const handleCopilotEditQueuedMessage = useCallback(
-    (id: string) => {
-      const msg = copilotEditQueuedMessage(id)
-      if (msg) setCopilotEditingInputValue(msg.content)
-    },
-    [copilotEditQueuedMessage]
-  )
-
   const handleCopilotStopGeneration = useCallback(() => {
     captureEvent(posthogRef.current, 'task_generation_aborted', {
       workspace_id: workspaceId,
@@ -865,11 +854,9 @@ export const Panel = memo(function Panel({ workspaceId: propWorkspaceId }: Panel
                   messageQueue={copilotMessageQueue}
                   onRemoveQueuedMessage={copilotRemoveFromQueue}
                   onSendQueuedMessage={copilotSendNow}
-                  onEditQueuedMessage={handleCopilotEditQueuedMessage}
+                  onEditQueuedMessage={copilotEditQueuedMessage}
                   userId={session?.user?.id}
                   chatId={copilotResolvedChatId}
-                  editValue={copilotEditingInputValue}
-                  onEditValueConsumed={clearCopilotEditingValue}
                   layout='copilot-view'
                 />
               </div>