diff --git a/src/components/layout/content.tsx b/src/components/layout/content.tsx
index c2023df..a49b643 100644
--- a/src/components/layout/content.tsx
+++ b/src/components/layout/content.tsx
@@ -11,6 +11,7 @@ import { Heading } from '../ui/heading.tsx'
 import { LoadingState } from '../ui/loading-state.tsx'
 import { PageTitle } from '../ui/page-title.tsx'
 import DragNDrop from '../upload/drag-n-drop.tsx'
+import { UploadError } from '../upload/upload-error.tsx'
 import { UploadStatus } from '../upload/upload-status.tsx'
 
 // Completed state for displaying upload history
@@ -87,6 +88,10 @@ export default function Content() {
       {showActiveUpload && uploadedFile && (
         <div className="space-y-6">
           <Heading tag="h2">Current upload</Heading>
+
+          {/* Show error alert if upload failed */}
+          <UploadError orchestration={orchestration} />
+
           <UploadStatus
             cid={activeUpload.currentCid}
             fileName={uploadedFile.file.name}
diff --git a/src/components/ui/alert.tsx b/src/components/ui/alert.tsx
index 901d1d9..c5ec7a0 100644
--- a/src/components/ui/alert.tsx
+++ b/src/components/ui/alert.tsx
@@ -1,73 +1,137 @@
+import { cva, type VariantProps } from 'class-variance-authority'
 import { clsx } from 'clsx'
-import { AlertTriangle, CircleAlert, CircleCheck } from 'lucide-react'
+import { AlertTriangle, CircleAlert, CircleCheck, Info, type LucideIcon } from 'lucide-react'
+import { ButtonBase } from '@/components/ui/button/button-base.tsx'
 
-const variantConfig = {
-  success: {
-    containerClass: 'bg-green-950/60 border border-green-900/40',
-    textClass: 'text-green-300',
-    iconClass: 'text-green-300',
-    Icon: CircleCheck,
-    buttonClass: 'bg-green-700 hover:bg-green-600 text-green-50',
+const alertVariants = cva('flex items-center gap-3 p-4 rounded-xl border', {
+  variants: {
+    variant: {
+      success: 'bg-green-950/60 border-green-900/40 text-green-200',
+      error: 'bg-red-950/60 border-red-900/40 text-red-300',
+      info: 'bg-brand-950/60 border-brand-900/40 text-brand-400',
+      warning: 'bg-yellow-600/30 border-yellow-400/20 text-yellow-100',
+      neutral: 'bg-zinc-900 border-zinc-700/40 text-zinc-100',
+    },
   },
-  error: {
-    containerClass: 'bg-red-950/60 border border-red-900/40',
-    textClass: 'text-red-300',
-    iconClass: 'text-red-300',
-    Icon: AlertTriangle,
-    buttonClass: 'bg-red-700 hover:bg-red-600 text-red-50',
+  defaultVariants: {
+    variant: 'neutral',
   },
-  info: {
-    containerClass: 'bg-brand-950/60 border border-brand-900/40',
-    textClass: 'text-brand-500',
-    iconClass: 'text-brand-500',
-    Icon: CircleCheck,
-    buttonClass: 'bg-brand-700 hover:bg-brand-600 text-brand-50',
+})
+
+const messageVariants = cva('text-base', {
+  variants: {
+    variant: {
+      success: 'text-green-300',
+      error: 'text-red-400',
+      info: 'text-brand-500',
+      warning: 'text-yellow-200',
+      neutral: 'text-zinc-100',
+    },
   },
-  warning: {
-    containerClass: 'bg-yellow-600/30 border border-yellow-400/20',
-    textClass: 'text-yellow-200',
-    iconClass: 'text-yellow-200',
-    Icon: CircleAlert,
-    buttonClass: 'bg-yellow-700 hover:bg-yellow-600 text-white',
+})
+
+const descriptionVariants = cva('', {
+  variants: {
+    variant: {
+      success: 'text-green-200',
+      error: 'text-red-300',
+      info: 'text-brand-400',
+      warning: 'text-yellow-100',
+      neutral: 'text-zinc-200',
+    },
   },
-  neutral: {
-    containerClass: 'bg-zinc-900 border border-zinc-700/40',
-    textClass: 'text-zinc-100',
-    iconClass: 'text-zinc-400',
-    Icon: CircleAlert,
-    buttonClass: 'bg-zinc-700 hover:bg-zinc-600 text-zinc-100',
+})
+
+const iconVariants = cva('', {
+  variants: {
+    variant: {
+      success: 'text-green-300',
+      error: 'text-red-400',
+      info: 'text-brand-500',
+      warning: 'text-yellow-200',
+      neutral: 'text-zinc-400',
+    },
   },
-}
+})
+
+const sharedButtonStyle = 'w-fit flex-shrink-0'
+
+const primaryButtonVariants = cva(sharedButtonStyle, {
+  variants: {
+    variant: {
+      success: 'bg-green-700 hover:bg-green-600 text-green-50',
+      error: 'bg-red-700 hover:bg-red-600 text-red-50',
+      info: 'bg-brand-700 hover:bg-brand-600 text-brand-50',
+      warning: 'bg-yellow-700 hover:bg-yellow-600 text-white',
+      neutral: 'bg-zinc-700 hover:bg-zinc-600 text-zinc-100',
+    },
+  },
+})
+
+const secondaryButtonVariants = cva(sharedButtonStyle, {
+  variants: {
+    variant: {
+      success: 'hover:bg-green-950/90 border border-green-700 text-green-500',
+      error: 'hover:bg-red-950/90 border border-red-700 text-red-500',
+      info: 'hover:bg-brand-950/90 border border-brand-700 text-brand-500',
+      warning: 'hover:bg-yellow-950/90 border border-yellow-700 text-yellow-500',
+      neutral: 'hover:bg-zinc-950/90 border border-zinc-600 text-zinc-400',
+    },
+  },
+})
+
+export type AlertVariant = NonNullable<VariantProps<typeof alertVariants>['variant']>
 
-export type AlertVariant = keyof typeof variantConfig
+type ButtonType = {
+  children: React.ReactNode
+  onClick?: React.ComponentProps<'button'>['onClick']
+}
 
 type AlertProps = {
-  variant: AlertVariant
+  variant?: AlertVariant
   message: string
-  button?: {
-    children: string
-    onClick: React.ComponentProps<'button'>['onClick']
-  }
+  description?: string
+  button?: ButtonType
+  cancelButton?: ButtonType
+}
+
+const ICONS: Record<AlertVariant, LucideIcon> = {
+  success: CircleCheck,
+  error: AlertTriangle,
+  info: Info,
+  warning: CircleAlert,
+  neutral: CircleAlert,
 }
 
-function Alert({ variant, message, button }: AlertProps) {
-  const { containerClass, textClass, iconClass, buttonClass, Icon } = variantConfig[variant]
+export function Alert({ variant = 'neutral', message, description, button, cancelButton }: AlertProps) {
+  const Icon = ICONS[variant]
 
   return (
-    <div className={clsx(containerClass, 'flex items-center gap-3 p-4 rounded-xl')} role="alert">
-      <span aria-hidden="true" className={iconClass}>
+    <div className={alertVariants({ variant })} role="alert">
+      <span aria-hidden="true" className={iconVariants({ variant })}>
         <Icon size={22} />
       </span>
-      <span className={clsx(textClass, 'flex-1')}>{message}</span>
-      {button && (
-        <button
-          className={clsx(buttonClass, 'px-4 py-2 rounded-lg font-medium flex-shrink-0 cursor-pointer')}
-          type="button"
-          {...button}
-        />
+
+      <div className="flex-1 flex flex-col gap-0.5">
+        <span className={clsx(messageVariants({ variant }), description && 'font-semibold')}>{message}</span>
+        {description && <span className={descriptionVariants({ variant })}>{description}</span>}
+      </div>
+
+      {(button || cancelButton) && (
+        <div className="flex gap-3">
+          {cancelButton && (
+            <ButtonBase
+              {...cancelButton}
+              className={secondaryButtonVariants({ variant })}
+              size="sm"
+              variant="unstyled"
+            />
+          )}
+          {button && (
+            <ButtonBase {...button} className={primaryButtonVariants({ variant })} size="sm" variant="unstyled" />
+          )}
+        </div>
       )}
     </div>
   )
 }
-
-export { Alert }
diff --git a/src/components/ui/button/button-base.tsx b/src/components/ui/button/button-base.tsx
index 1e4eafc..ddb1ab0 100644
--- a/src/components/ui/button/button-base.tsx
+++ b/src/components/ui/button/button-base.tsx
@@ -2,12 +2,18 @@ import { cva, type VariantProps } from 'class-variance-authority'
 import { cn } from '@/utils/cn.ts'
 
 const buttonVariants = cva(
-  'inline-flex items-center justify-center font-medium px-5 py-3 rounded-md transition-colors w-full hover:opacity-90',
+  'inline-flex items-center justify-center font-medium transition-colors w-full cursor-pointer',
   {
     variants: {
       variant: {
-        primary: 'bg-brand-800 text-zinc-100 border border-transparent disabled:bg-button-brand-disabled',
+        primary:
+          'bg-brand-800 text-zinc-100 border border-transparent disabled:bg-button-brand-disabled hover:bg-brand-700',
         secondary: 'bg-transparent text-zinc-100 border border-zinc-800 hover:bg-zinc-800',
+        unstyled: '',
+      },
+      size: {
+        sm: 'text-sm px-4 py-2 rounded-md',
+        md: 'text-base px-5 py-3 rounded-lg',
       },
       loading: {
         true: 'cursor-wait',
@@ -19,6 +25,7 @@ const buttonVariants = cva(
       },
     },
     defaultVariants: {
+      size: 'md',
       variant: 'primary',
       loading: false,
       disabled: false,
@@ -31,10 +38,10 @@ type ButtonBaseProps = React.ButtonHTMLAttributes<HTMLButtonElement> &
     loading?: boolean
   }
 
-function ButtonBase({ className, variant, loading, children, disabled, ...props }: ButtonBaseProps) {
+function ButtonBase({ className, variant, loading, children, disabled, size = 'md', ...props }: ButtonBaseProps) {
   return (
     <button
-      className={cn(buttonVariants({ variant, loading, disabled, className }))}
+      className={cn(buttonVariants({ variant, loading, disabled, className, size }))}
       disabled={disabled || loading}
       {...props}
     >
diff --git a/src/components/upload/upload-error.tsx b/src/components/upload/upload-error.tsx
new file mode 100644
index 0000000..0875635
--- /dev/null
+++ b/src/components/upload/upload-error.tsx
@@ -0,0 +1,26 @@
+import type { useUploadOrchestration } from '../../hooks/use-upload-orchestration.ts'
+import { Alert } from '../ui/alert.tsx'
+
+interface UploadErrorProps {
+  orchestration: ReturnType<typeof useUploadOrchestration>
+}
+
+function UploadError({ orchestration }: UploadErrorProps) {
+  const { activeUpload, uploadedFile, retryUpload, cancelUpload } = orchestration
+
+  if (!activeUpload.error) {
+    return null
+  }
+
+  return (
+    <Alert
+      button={{ children: 'Retry Upload', onClick: retryUpload }}
+      cancelButton={{ children: 'Cancel', onClick: cancelUpload }}
+      description={activeUpload.error}
+      message={`Upload failed - ${uploadedFile?.file.name}`}
+      variant="error"
+    />
+  )
+}
+
+export { UploadError }
diff --git a/src/hooks/use-filecoin-upload.ts b/src/hooks/use-filecoin-upload.ts
index 8567669..8cd6a82 100644
--- a/src/hooks/use-filecoin-upload.ts
+++ b/src/hooks/use-filecoin-upload.ts
@@ -1,7 +1,7 @@
 import { createCarFromFile } from 'filecoin-pin/core/unixfs'
 import { checkUploadReadiness, executeUpload } from 'filecoin-pin/core/upload'
 import pino from 'pino'
-import { useCallback, useMemo, useState } from 'react'
+import { useCallback, useEffect, useMemo, useRef, useState } from 'react'
 import type { Progress } from '../types/upload-progress.ts'
 import { formatFileSize } from '../utils/format-file-size.ts'
 import { useFilecoinPinContext } from './use-filecoin-pin-context.ts'
@@ -51,7 +51,17 @@ export const INPI_ERROR_MESSAGE =
  * actions so they stay dumb and declarative.
  */
 export const useFilecoinUpload = () => {
-  const { synapse, storageContext, providerInfo } = useFilecoinPinContext()
+  const { synapse, storageContext, providerInfo, ensureDataSet } = useFilecoinPinContext()
+
+  // Use refs to track the latest context values, so the upload callback can access them
+  // even if the dataset is initialized after the callback is created
+  const storageContextRef = useRef(storageContext)
+  const providerInfoRef = useRef(providerInfo)
+
+  useEffect(() => {
+    storageContextRef.current = storageContext
+    providerInfoRef.current = providerInfo
+  }, [storageContext, providerInfo])
 
   const [uploadState, setUploadState] = useState<UploadState>({
     isUploading: false,
@@ -149,20 +159,27 @@ export const useFilecoinUpload = () => {
           },
         })
 
-        // Ensure we have storage context from provider (created during data set initialization)
-        if (!storageContext || !providerInfo) {
-          // This should never happen because the upload button is disabled if the data set is not ready
-          throw new Error('Storage context not ready. Please ensure a data set is initialized before uploading.')
+        // Ensure we have a data set ready before uploading
+        console.debug('[FilecoinUpload] Ensuring data set is ready before upload...')
+        await ensureDataSet()
+
+        // Get the latest storage context and provider info from refs
+        // (these may have been updated by ensureDataSet if dataset wasn't ready)
+        const currentStorageContext = storageContextRef.current
+        const currentProviderInfo = providerInfoRef.current
+
+        if (!currentStorageContext || !currentProviderInfo) {
+          throw new Error('Storage context not ready. Failed to initialize data set. Please try again.')
         }
 
         console.debug('[FilecoinUpload] Using storage context from provider:', {
-          providerInfo,
-          dataSetId: storageContext.dataSetId,
+          providerInfo: currentProviderInfo,
+          dataSetId: currentStorageContext.dataSetId,
         })
 
         const synapseService = {
-          storage: storageContext,
-          providerInfo,
+          storage: currentStorageContext,
+          providerInfo: currentProviderInfo,
           synapse,
         }
 
@@ -226,7 +243,7 @@ export const useFilecoinUpload = () => {
         }))
       }
     },
-    [updateProgress, synapse, storageContext, providerInfo]
+    [updateProgress, synapse, ensureDataSet]
   )
 
   const resetUpload = useCallback(() => {
diff --git a/src/hooks/use-upload-orchestration.ts b/src/hooks/use-upload-orchestration.ts
index 9e7d1b9..85d8394 100644
--- a/src/hooks/use-upload-orchestration.ts
+++ b/src/hooks/use-upload-orchestration.ts
@@ -116,23 +116,6 @@ export function useUploadOrchestration() {
     resetUpload,
   ])
 
-  /**
-   * Auto-clear upload state on error after 5 seconds
-   * This gives users time to see the error before resetting the UI
-   */
-  useEffect(() => {
-    if (uploadState.error) {
-      console.debug('[UploadOrchestration] Upload error detected, will auto-clear in 5 seconds')
-      const timer = setTimeout(() => {
-        setUploadedFile(null)
-        resetUpload()
-        // Increment key to force DragNDrop to remount and clear its state
-        setDragDropKey((prev) => prev + 1)
-      }, 5000)
-      return () => clearTimeout(timer)
-    }
-  }, [uploadState.error, resetUpload])
-
   /**
    * Start an upload and track the file metadata.
    * Sets uploadedFile immediately to switch UI to progress view.
@@ -163,6 +146,31 @@ export function useUploadOrchestration() {
     [uploadFile]
   )
 
+  /**
+   * Clear upload state and reset to upload form.
+   * Called when user dismisses an error or cancels an upload.
+   */
+  const cancelUpload = useCallback(() => {
+    console.debug('[UploadOrchestration] Canceling upload')
+    setUploadedFile(null)
+    resetUpload()
+    // Increment key to force DragNDrop to remount and clear its state
+    setDragDropKey((prev) => prev + 1)
+  }, [resetUpload])
+
+  /**
+   * Retry a failed upload with the same file.
+   * Only works if there's an uploadedFile and an error state.
+   */
+  const retryUpload = useCallback(() => {
+    if (!uploadedFile) {
+      console.warn('[UploadOrchestration] Cannot retry: no file in uploadedFile state')
+      return
+    }
+    console.debug('[UploadOrchestration] Retrying upload for file:', uploadedFile.file.name)
+    handleUpload(uploadedFile.file)
+  }, [uploadedFile, handleUpload])
+
   return {
     /**
      * The file currently being uploaded (with metadata like name, size)
@@ -193,5 +201,17 @@ export function useUploadOrchestration() {
      * @param file - File to upload
      */
     startUpload: handleUpload,
+
+    /**
+     * Retry the current failed upload
+     * Re-uploads the same file that previously failed
+     */
+    retryUpload,
+
+    /**
+     * Cancel the current upload and clear error state
+     * Returns user to the upload form
+     */
+    cancelUpload,
   }
 }