diff --git a/packages/web/src/files/PickedFileItem.tsx b/packages/web/src/files/PickedFileItem.tsx
new file mode 100644
index 0000000..1e5ecdd
--- /dev/null
+++ b/packages/web/src/files/PickedFileItem.tsx
@@ -0,0 +1,71 @@
+import { useAtomValue } from "jotai"
+import { CircleAlertIcon, XIcon } from "lucide-react"
+import type React from "react"
+import { Button } from "@/components/ui/button"
+import { Progress } from "@/components/ui/progress"
+import { Tooltip } from "@/components/ui/tooltip"
+import { FileUploadStatusKind, fileUploadStatusAtomFamily } from "./store"
+import type { PickedFile } from "./upload-file-dialog"
+
+export function PickedFileItem({
+	file: pickedFile,
+	onRemove,
+}: {
+	file: PickedFile
+	onRemove: (file: PickedFile) => void
+}) {
+	const fileUploadAtom = fileUploadStatusAtomFamily(pickedFile.id)
+	const fileUpload = useAtomValue(fileUploadAtom)
+	console.log("fileUpload", fileUpload)
+	const { file, id } = pickedFile
+
+	let statusIndicator: React.ReactNode
+	if (!fileUpload) {
+		statusIndicator = (
+			<Button
+				variant="ghost"
+				size="icon"
+				onClick={() => onRemove(pickedFile)}
+			>
+				<XIcon className="size-4" />
+			</Button>
+		)
+	} else {
+		switch (fileUpload.kind) {
+			case FileUploadStatusKind.InProgress:
+				statusIndicator = <Progress value={fileUpload.progress * 100} />
+				break
+			case FileUploadStatusKind.Error:
+				statusIndicator = (
+					<Tooltip>
+						<TooltipTrigger>
+							<CircleAlertIcon />
+						</TooltipTrigger>
+					</Tooltip>
+				)
+		}
+	}
+
+	return (
+		<li
+			className="pl-3 pr-1 py-0.5 h-8 hover:bg-muted flex justify-between items-center"
+			key={id}
+		>
+			<span>{file.name}</span>
+			{fileUpload ? (
+				<Progress
+					className="max-w-20"
+					value={fileUpload.progress * 100}
+				/>
+			) : (
+				<Button
+					variant="ghost"
+					size="icon"
+					onClick={() => onRemove(pickedFile)}
+				>
+					<XIcon className="size-4" />
+				</Button>
+			)}
+		</li>
+	)
+}
diff --git a/packages/web/src/files/store.ts b/packages/web/src/files/store.ts
index b33cb0b..4d4513a 100644
--- a/packages/web/src/files/store.ts
+++ b/packages/web/src/files/store.ts
@@ -1,19 +1,39 @@
 import { atom } from "jotai"
 import { atomFamily } from "jotai/utils"
 
-type FileUpload = {
-	id: string
+export enum FileUploadStatusKind {
+	InProgress = "InProgress",
+	Error = "Error",
+	Success = "Success",
+}
+
+export type FileUploadInProgress = {
+	kind: FileUploadStatusKind.InProgress
 	progress: number
 }
 
-export const fileUploadsAtom = atom<Record<string, FileUpload>>({})
+export type FileUploadError = {
+	kind: FileUploadStatusKind.Error
+	error: unknown
+}
 
-export const fileUploadAtomFamily = atomFamily((id: string) =>
+export type FileUploadSuccess = {
+	kind: FileUploadStatusKind.Success
+}
+
+export type FileUploadStatus =
+	| FileUploadInProgress
+	| FileUploadError
+	| FileUploadSuccess
+
+export const fileUploadsAtom = atom<Record<string, FileUploadStatus>>({})
+
+export const fileUploadStatusAtomFamily = atomFamily((id: string) =>
 	atom(
 		(get) => get(fileUploadsAtom)[id],
-		(get, set, progress: number) => {
+		(get, set, status: FileUploadStatus) => {
 			const fileUploads = { ...get(fileUploadsAtom) }
-			fileUploads[id] = { id, progress }
+			fileUploads[id] = status
 			set(fileUploadsAtom, fileUploads)
 		},
 	),
@@ -22,12 +42,56 @@ export const fileUploadAtomFamily = atomFamily((id: string) =>
 export const clearFileUploadAtom = atom(null, (get, set, id: string) => {
 	const fileUploads = { ...get(fileUploadsAtom) }
 	delete fileUploads[id]
-	fileUploadAtomFamily.remove(id)
+	fileUploadStatusAtomFamily.remove(id)
 	set(fileUploadsAtom, fileUploads)
 })
 
+export const clearFileUploadStatusesAtom = atom(
+	null,
+	(get, set, ids: string[]) => {
+		const fileUploads = { ...get(fileUploadsAtom) }
+		for (const id of ids) {
+			if (fileUploads[id]) {
+				delete fileUploads[id]
+			}
+			fileUploadStatusAtomFamily.remove(id)
+		}
+		set(fileUploadsAtom, fileUploads)
+	},
+)
+
 export const fileUploadCountAtom = atom(
 	(get) => Object.keys(get(fileUploadsAtom)).length,
 )
 
-export const hasFileUploadsAtom = atom((get) => get(fileUploadCountAtom) > 0)
+export const inProgressFileUploadCountAtom = atom((get) => {
+	const statuses = get(fileUploadsAtom)
+	let count = 0
+	for (const status in statuses) {
+		if (statuses[status]?.kind === FileUploadStatusKind.InProgress) {
+			count += 1
+		}
+	}
+	return count
+})
+
+export const successfulFileUploadCountAtom = atom((get) => {
+	const statuses = get(fileUploadsAtom)
+	let count = 0
+	for (const status in statuses) {
+		if (statuses[status]?.kind === FileUploadStatusKind.Success) {
+			count += 1
+		}
+	}
+	return count
+})
+
+export const hasFileUploadsErrorAtom = atom((get) => {
+	const statuses = get(fileUploadsAtom)
+	for (const status in statuses) {
+		if (statuses[status]?.kind === FileUploadStatusKind.Error) {
+			return true
+		}
+	}
+	return false
+})
diff --git a/packages/web/src/files/upload-file-dialog.tsx b/packages/web/src/files/upload-file-dialog.tsx
index a63a35b..de8e519 100644
--- a/packages/web/src/files/upload-file-dialog.tsx
+++ b/packages/web/src/files/upload-file-dialog.tsx
@@ -2,7 +2,13 @@ import type { Doc } from "@fileone/convex/_generated/dataModel"
 import { useMutation } from "@tanstack/react-query"
 import { atom, useAtom, useAtomValue, useSetAtom, useStore } from "jotai"
 import { atomEffect } from "jotai-effect"
-import { FilePlus2Icon, UploadCloudIcon, XIcon } from "lucide-react"
+import {
+	CircleAlertIcon,
+	CircleCheckIcon,
+	FilePlus2Icon,
+	UploadCloudIcon,
+	XIcon,
+} from "lucide-react"
 import { nanoid } from "nanoid"
 import type React from "react"
 import { useId, useMemo, useRef, useState } from "react"
@@ -17,8 +23,21 @@ import {
 	DialogTitle,
 } from "@/components/ui/dialog"
 import { Progress } from "@/components/ui/progress"
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipTrigger,
+} from "@/components/ui/tooltip"
 import { WithAtom } from "@/components/with-atom"
-import { clearFileUploadAtom, fileUploadAtomFamily } from "./store"
+import { formatError } from "@/lib/error"
+import {
+	clearFileUploadStatusesAtom,
+	FileUploadStatusKind,
+	fileUploadCountAtom,
+	fileUploadStatusAtomFamily,
+	fileUploadsAtom,
+	hasFileUploadsErrorAtom,
+} from "./store"
 import useUploadFile from "./use-upload-file"
 
 type UploadFileDialogProps = {
@@ -41,7 +60,7 @@ export function UploadFileDialog({
 	const formId = useId()
 	const fileInputRef = useRef<HTMLInputElement>(null)
 	const setPickedFiles = useSetAtom(pickedFilesAtom)
-	const clearFileUpload = useSetAtom(clearFileUploadAtom)
+	const clearFileUploadStatuses = useSetAtom(clearFileUploadStatusesAtom)
 	const store = useStore()
 
 	const updateFileInputEffect = useMemo(
@@ -69,21 +88,58 @@ export function UploadFileDialog({
 				uploadFile({
 					file: pickedFile.file,
 					onStart: () => {
-						store.set(fileUploadAtomFamily(pickedFile.id), 0)
+						store.set(fileUploadStatusAtomFamily(pickedFile.id), {
+							kind: FileUploadStatusKind.InProgress,
+							progress: 0,
+						})
 					},
 					onProgress: (progress) => {
-						store.set(fileUploadAtomFamily(pickedFile.id), progress)
+						store.set(fileUploadStatusAtomFamily(pickedFile.id), {
+							kind: FileUploadStatusKind.InProgress,
+							progress,
+						})
 					},
-				}).then(() => {
-					clearFileUpload(pickedFile.id)
-				}),
+				})
+					.then(() => {
+						// clearFileUpload(pickedFile.id)
+					})
+					.catch((error) => {
+						console.log("error", error)
+						store.set(fileUploadStatusAtomFamily(pickedFile.id), {
+							kind: FileUploadStatusKind.Error,
+							error,
+						})
+						throw error
+					}),
 			)
-			await Promise.all(promises)
+			return await Promise.allSettled(promises)
 		},
-		onSuccess: () => {
-			toast.success("All files uploaded successfully")
-			setPickedFiles([])
-			onClose()
+		onSuccess: (results, files) => {
+			const remainingPickedFiles: PickedFile[] = []
+			results.forEach((result, i) => {
+				// biome-ignore lint/style/noNonNullAssertion: results lenght must match input files array length
+				const pickedFile = files[i]!
+				const statusAtom = fileUploadStatusAtomFamily(pickedFile.id)
+				switch (result.status) {
+					case "fulfilled":
+						store.set(statusAtom, {
+							kind: FileUploadStatusKind.Success,
+						})
+						break
+					case "rejected":
+						store.set(statusAtom, {
+							kind: FileUploadStatusKind.Error,
+							error: result.reason,
+						})
+						remainingPickedFiles.push(pickedFile)
+						break
+				}
+			})
+			// setPickedFiles(remainingPickedFiles)
+
+			if (remainingPickedFiles.length === 0) {
+				toast.success("All files uploaded successfully")
+			}
 		},
 	})
 
@@ -105,9 +161,50 @@ export function UploadFileDialog({
 		}
 	}
 
-	function startFileUpload() {
+	function onUploadButtonClick() {
+		const uploadStatuses = store.get(fileUploadsAtom)
+		const fileUploadCount = store.get(fileUploadCountAtom)
 		const pickedFiles = store.get(pickedFilesAtom)
-		uploadFiles(pickedFiles)
+
+		if (pickedFiles.length === 0) {
+			// no files are picked, nothing to upload
+			return
+		}
+
+		if (fileUploadCount === 0) {
+			// no files are being uploaded, upload all picked files
+			uploadFiles(pickedFiles)
+			return
+		}
+
+		const successfulUploads: PickedFile["id"][] = []
+		const nextPickedFiles: PickedFile[] = []
+		for (const file of pickedFiles) {
+			const uploadStatus = uploadStatuses[file.id]
+			if (uploadStatus) {
+				switch (uploadStatus.kind) {
+					case FileUploadStatusKind.Success:
+						successfulUploads.push(file.id)
+						continue
+					case FileUploadStatusKind.InProgress:
+						continue
+					case FileUploadStatusKind.Error:
+						nextPickedFiles.push(file)
+						break
+				}
+			}
+		}
+
+		clearFileUploadStatuses(successfulUploads)
+
+		if (successfulUploads.length === pickedFiles.length) {
+			// all files were successfully uploaded, close the dialog
+			onClose()
+		} else {
+			// some files were not successfully uploaded, set the next picked files
+			setPickedFiles(nextPickedFiles)
+			uploadFiles(nextPickedFiles)
+		}
 	}
 
 	let dialogTitle: string
@@ -165,15 +262,11 @@ export function UploadFileDialog({
 										Select more files
 									</Button>
 								) : null}
-								<Button
-									onClick={startFileUpload}
+								<UploadButton
 									disabled={isUploading}
 									loading={isUploading}
-								>
-									{pickedFiles.length === 0
-										? "Upload"
-										: `Upload ${pickedFiles.length} files`}
-								</Button>
+									onClick={onUploadButtonClick}
+								/>
 							</>
 						)}
 					</WithAtom>
@@ -183,6 +276,39 @@ export function UploadFileDialog({
 	)
 }
 
+function UploadButton({
+	disabled,
+	loading,
+	onClick,
+}: {
+	disabled: boolean
+	loading: boolean
+	onClick: () => void
+}) {
+	const pickedFiles = useAtomValue(pickedFilesAtom)
+	const hasUploadErrors = useAtomValue(hasFileUploadsErrorAtom)
+	const fileUploadCount = useAtomValue(fileUploadCountAtom)
+
+	let label: string
+	if (hasUploadErrors) {
+		label = "Retry failed uploads"
+	} else if (pickedFiles.length > 0) {
+		if (fileUploadCount > 0) {
+			label = "Done"
+		} else {
+			label = `Upload ${pickedFiles.length} files`
+		}
+	} else {
+		label = "Upload"
+	}
+
+	return (
+		<Button onClick={onClick} disabled={disabled} loading={loading}>
+			{label}
+		</Button>
+	)
+}
+
 function UploadFileDropContainer({ children }: React.PropsWithChildren) {
 	const [draggedFiles, setDraggedFiles] = useState<DataTransferItem[]>([])
 	const setPickedFiles = useSetAtom(pickedFilesAtom)
@@ -239,6 +365,7 @@ function UploadFileDropContainer({ children }: React.PropsWithChildren) {
 	)
 }
 
+// tag: uploadfilearea area fileuploadarea
 function UploadFileArea({ onClick }: { onClick: () => void }) {
 	const [pickedFiles, setPickedFiles] = useAtom(pickedFilesAtom)
 
@@ -294,30 +421,62 @@ function PickedFileItem({
 	file: PickedFile
 	onRemove: (file: PickedFile) => void
 }) {
-	const fileUploadAtom = fileUploadAtomFamily(pickedFile.id)
+	const fileUploadAtom = fileUploadStatusAtomFamily(pickedFile.id)
 	const fileUpload = useAtomValue(fileUploadAtom)
 	console.log("fileUpload", fileUpload)
 	const { file, id } = pickedFile
+
+	let statusIndicator: React.ReactNode
+	if (!fileUpload) {
+		statusIndicator = (
+			<Button
+				variant="ghost"
+				size="icon"
+				onClick={() => onRemove(pickedFile)}
+			>
+				<XIcon className="size-4" />
+			</Button>
+		)
+	} else {
+		switch (fileUpload.kind) {
+			case FileUploadStatusKind.InProgress:
+				statusIndicator = (
+					<Progress
+						className="max-w-20"
+						value={fileUpload.progress * 100}
+					/>
+				)
+				break
+			case FileUploadStatusKind.Error:
+				statusIndicator = (
+					<Tooltip>
+						<TooltipTrigger>
+							<CircleAlertIcon className="pr-2 text-destructive" />
+						</TooltipTrigger>
+						<TooltipContent>
+							<p>
+								Failed to upload file:{" "}
+								{formatError(fileUpload.error)}
+							</p>
+						</TooltipContent>
+					</Tooltip>
+				)
+				break
+			case FileUploadStatusKind.Success:
+				statusIndicator = (
+					<CircleCheckIcon className="pr-2 text-green-500" />
+				)
+				break
+		}
+	}
+
 	return (
 		<li
 			className="pl-3 pr-1 py-0.5 h-8 hover:bg-muted flex justify-between items-center"
 			key={id}
 		>
 			<span>{file.name}</span>
-			{fileUpload ? (
-				<Progress
-					className="max-w-20"
-					value={fileUpload.progress * 100}
-				/>
-			) : (
-				<Button
-					variant="ghost"
-					size="icon"
-					onClick={() => onRemove(pickedFile)}
-				>
-					<XIcon className="size-4" />
-				</Button>
-			)}
+			{statusIndicator}
 		</li>
 	)
 }
diff --git a/packages/web/src/files/use-upload-file.ts b/packages/web/src/files/use-upload-file.ts
index 08a72ec..098b094 100644
--- a/packages/web/src/files/use-upload-file.ts
+++ b/packages/web/src/files/use-upload-file.ts
@@ -29,7 +29,6 @@ function useUploadFile({
 			})
 			xhr.upload.addEventListener("error", reject)
 			xhr.addEventListener("load", () => {
-				console.log("load", xhr.response)
 				resolve(
 					xhr.response as {
 						storageId: Id<"_storage">
diff --git a/packages/web/src/routes/_authenticated/_sidebar-layout/directories.$directoryId.tsx b/packages/web/src/routes/_authenticated/_sidebar-layout/directories.$directoryId.tsx
index 6c197a4..0a23d6c 100644
--- a/packages/web/src/routes/_authenticated/_sidebar-layout/directories.$directoryId.tsx
+++ b/packages/web/src/routes/_authenticated/_sidebar-layout/directories.$directoryId.tsx
@@ -44,7 +44,7 @@ import { FilePathBreadcrumb } from "@/directories/directory-page/file-path-bread
 import { NewDirectoryDialog } from "@/directories/directory-page/new-directory-dialog"
 import { RenameFileDialog } from "@/directories/directory-page/rename-file-dialog"
 import { FilePreviewDialog } from "@/files/file-preview-dialog"
-import { fileUploadCountAtom } from "@/files/store"
+import { inProgressFileUploadCountAtom } from "@/files/store"
 import { UploadFileDialog } from "@/files/upload-file-dialog"
 import type { FileDragInfo } from "@/files/use-file-drop"
 
@@ -333,7 +333,9 @@ function RenameMenuItem() {
 function UploadFileButton() {
 	const { directory } = useContext(DirectoryPageContext)
 	const setActiveDialogData = useSetAtom(activeDialogDataAtom)
-	const fileUploadCount = useAtomValue(fileUploadCountAtom)
+	const inProgressFileUploadCount = useAtomValue(
+		inProgressFileUploadCountAtom,
+	)
 
 	const handleClick = () => {
 		setActiveDialogData({
@@ -342,10 +344,10 @@ function UploadFileButton() {
 		})
 	}
 
-	if (fileUploadCount > 0) {
+	if (inProgressFileUploadCount > 0) {
 		return (
 			<Button size="sm" type="button" loading onClick={handleClick}>
-				Uploading {fileUploadCount} files
+				Uploading {inProgressFileUploadCount} files
 			</Button>
 		)
 	}