diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/ConfirmPurgeModal.tsx b/apps/studio/components/interfaces/Storage/StorageExplorer/ConfirmPurgeModal.tsx
index 9c61a5e4575..b6ff6d95b07 100644
--- a/apps/studio/components/interfaces/Storage/StorageExplorer/ConfirmPurgeModal.tsx
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/ConfirmPurgeModal.tsx
@@ -1,7 +1,7 @@
 import { toast } from 'sonner'
 import { ConfirmationModal } from 'ui-patterns/Dialogs/ConfirmationModal'
 
-import { getPathAlongOpenedFolders } from './StorageExplorer.utils'
+import { getStorageItemPath } from './StorageExplorer.utils'
 import { useStorageExplorerNavigation } from './StorageExplorerNavigation'
 import { useObjectPurgeMutation } from '@/data/storage/versioning/object-purge-mutation'
 import { useStorageExplorerStateSnapshot } from '@/state/storage-explorer'
@@ -33,11 +33,7 @@ export const ConfirmPurgeModal = () => {
     if (!projectRef || !selectedBucket?.id || itemToPurge === undefined) return
 
     // The endpoint addresses an object by full path; a row only knows its leaf name.
-    const folderPath = getPathAlongOpenedFolders(
-      { openedFolders: openedFolders.slice(0, itemToPurge.columnIndex), selectedBucket },
-      false
-    )
-    const path = [folderPath, itemToPurge.name].filter(Boolean).join('/')
+    const path = getStorageItemPath({ openedFolders }, itemToPurge)
 
     purgeObject({ projectRef, bucketId: selectedBucket.id, path })
   }
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/FilePreview.test.tsx b/apps/studio/components/interfaces/Storage/StorageExplorer/FilePreview.test.tsx
index a1d11f83d93..7de9d0aec00 100644
--- a/apps/studio/components/interfaces/Storage/StorageExplorer/FilePreview.test.tsx
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/FilePreview.test.tsx
@@ -2,6 +2,7 @@ import { screen, waitFor } from '@testing-library/react'
 import { describe, expect, it, vi } from 'vitest'
 
 import { FilePreview } from '@/components/interfaces/Storage/StorageExplorer/FilePreview'
+import { fileUrlKey } from '@/components/interfaces/Storage/StorageExplorer/useFetchFileUrlQuery'
 import { customRender as render } from '@/tests/lib/custom-render'
 import { addAPIMock } from '@/tests/lib/msw'
 
@@ -65,6 +66,36 @@ describe('FilePreview', () => {
     )
   })
 
+  it('keys each version separately, so a new one cannot reuse the cached URL', () => {
+    const current = fileUrlKey({
+      projectRef: 'abcdef',
+      isBucketPublic: false,
+      bucketId: 'my-bucket',
+      path: 'photo.png',
+    })
+
+    expect(
+      fileUrlKey({
+        projectRef: 'abcdef',
+        isBucketPublic: false,
+        bucketId: 'my-bucket',
+        path: 'photo.png',
+        versionId: 'v-new',
+      })
+    ).not.toEqual(current)
+
+    // The version-less key is a prefix of every version's, so one invalidation clears all.
+    expect(
+      fileUrlKey({
+        projectRef: 'abcdef',
+        isBucketPublic: false,
+        bucketId: 'my-bucket',
+        path: 'photo.png',
+        versionId: 'v-new',
+      }).slice(0, current.length)
+    ).toEqual(current)
+  })
+
   it('skips the request for a file too large to preview', async () => {
     const bodies = mockSignEndpoint()
 
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/PreviewPane.tsx b/apps/studio/components/interfaces/Storage/StorageExplorer/PreviewPane.tsx
index 181df2a5022..c225ca069a4 100644
--- a/apps/studio/components/interfaces/Storage/StorageExplorer/PreviewPane.tsx
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/PreviewPane.tsx
@@ -1,6 +1,6 @@
 import { PermissionAction } from '@supabase/shared-types/out/constants'
 import { useQuery } from '@tanstack/react-query'
-import { AlertCircle, Archive, ChevronDown, Copy, Download, Trash2, X } from 'lucide-react'
+import { AlertCircle, Archive, ChevronDown, Copy, Download, Trash2, Upload, X } from 'lucide-react'
 import { parseAsBoolean, useQueryState } from 'nuqs'
 import { useRef, useState } from 'react'
 import { toast } from 'sonner'
@@ -18,6 +18,7 @@ import { URL_EXPIRY_DURATION } from '../Storage.constants'
 import { StorageItem } from '../Storage.types'
 import { getBucketVersioningState } from '../StorageVersioning.constants'
 import { FilePreview } from './FilePreview'
+import { pickFile } from './pickFile'
 import { PreviewSection } from './PreviewSection'
 import { getPathAlongOpenedFolders } from './StorageExplorer.utils'
 import { useStorageExplorerNavigation } from './StorageExplorerNavigation'
@@ -65,10 +66,13 @@ interface CurrentFilePreviewProps {
   size: string | null
   isPublicBucket: boolean
   isVersionedBucket: boolean
+  /** Pins the preview to the current version, so a new one busts the cached URL. */
+  currentVersionId?: string
   hasCurrentVersion: boolean
   canUpdateFiles: boolean
   onCopyUrl: (path: string, expiry?: number) => void
   onDownload: () => void
+  onReplace: () => void
   onCustomExpiry: () => void
   onDelete: () => void
   onPurge: () => void
@@ -81,10 +85,12 @@ const CurrentFilePreview = ({
   size,
   isPublicBucket,
   isVersionedBucket,
+  currentVersionId,
   hasCurrentVersion,
   canUpdateFiles,
   onCopyUrl,
   onDownload,
+  onReplace,
   onCustomExpiry,
   onDelete,
   onPurge,
@@ -94,7 +100,12 @@ const CurrentFilePreview = ({
       className="flex items-center justify-center overflow-hidden rounded-md border border-overlay"
       style={{ height: 'clamp(120px, calc((100vh - 144px) * 0.4), 180px)' }}
     >
-      <FilePreview path={path} mimeType={mimeType} size={file.metadata?.size} />
+      <FilePreview
+        path={path}
+        mimeType={mimeType}
+        size={file.metadata?.size}
+        versionId={currentVersionId}
+      />
     </div>
 
     <div className="mt-2 flex flex-col">
@@ -129,6 +140,21 @@ const CurrentFilePreview = ({
           tooltip={{ content: { side: 'top', text: 'Download current' } }}
         />
 
+        {canUpdateFiles && (
+          <ButtonTooltip
+            variant="outline"
+            className="px-2"
+            icon={<Upload size={14} />}
+            onClick={onReplace}
+            tooltip={{
+              content: {
+                side: 'top',
+                text: isVersionedBucket ? 'Upload new version' : 'Replace file',
+              },
+            }}
+          />
+        )}
+
         {isPublicBucket ? (
           <Button
             variant="outline"
@@ -233,6 +259,7 @@ export const PreviewPane = () => {
     setSelectedItemsToDelete,
     setItemToPurge,
     refetchAllOpenedFolders,
+    replaceFile,
     setSelectedFileCustomExpiry,
     downloadFile,
   } = useStorageExplorerStateSnapshot()
@@ -305,6 +332,11 @@ export const PreviewPane = () => {
     })
   }
 
+  const onReplaceFile = async () => {
+    const newFile = await pickFile()
+    if (newFile !== undefined) await replaceFile({ file: newFile, item: file })
+  }
+
   // The compare widget replaces the top of the panel, so scroll up to show it.
   const handlePreviewVersion = (version: ObjectVersion) => {
     setPreviewedVersion(version)
@@ -348,10 +380,12 @@ export const PreviewPane = () => {
             size={size}
             isPublicBucket={!!selectedBucket?.public}
             isVersionedBucket={isVersionedBucket}
+            currentVersionId={currentVersion?.versionId}
             hasCurrentVersion={currentVersion !== undefined}
             canUpdateFiles={canUpdateFiles}
             onCopyUrl={onCopyUrl}
             onDownload={() => downloadFile(file)}
+            onReplace={onReplaceFile}
             onCustomExpiry={() => setSelectedFileCustomExpiry(file)}
             onDelete={() => setSelectedItemsToDelete([file])}
             onPurge={() => setItemToPurge(file)}
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.test.ts b/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.test.ts
index 71876d4dfb2..4957abe6c66 100644
--- a/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.test.ts
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.test.ts
@@ -10,9 +10,11 @@ import type { StorageItem } from '@/components/interfaces/Storage/Storage.types'
 import {
   copyStorageExplorerUrl,
   copyStoragePath,
+  describeUploadFailure,
   getPathAlongFoldersToIndex,
   getPathAlongOpenedFolders,
   getStorageExplorerUrlForItem,
+  getStorageItemPath,
   getStoragePathForItem,
   parseStoragePath,
   sanitizeNameForDuplicateInColumn,
@@ -452,3 +454,57 @@ describe('clipboard helpers', () => {
     expect(toast.success).toHaveBeenCalledWith('Copied URL for "photo.png"')
   })
 })
+
+describe('getStorageItemPath', () => {
+  const openedFolders = [makeFolder('images'), makeFolder('2024'), makeFolder('january')]
+
+  it('returns the bare name for an item at the bucket root', () => {
+    expect(getStorageItemPath({ openedFolders }, { name: 'avatar.png', columnIndex: 0 })).toBe(
+      'avatar.png'
+    )
+  })
+
+  it('prefixes the folders opened above the item', () => {
+    expect(getStorageItemPath({ openedFolders }, { name: 'avatar.png', columnIndex: 2 })).toBe(
+      'images/2024/avatar.png'
+    )
+  })
+
+  it('ignores folders opened below the item', () => {
+    // The user drilled into january, but the item sits in the 2024 column.
+    expect(getStorageItemPath({ openedFolders }, { name: 'notes.txt', columnIndex: 1 })).toBe(
+      'images/notes.txt'
+    )
+  })
+})
+
+describe('describeUploadFailure', () => {
+  it('names the allowed types when the bucket rejects the mime type', () => {
+    expect(
+      describeUploadFailure({
+        status: 415,
+        fallback: 'tus: unexpected response',
+        allowedMimeTypes: ['image/png', 'image/jpeg'],
+      })
+    ).toBe(
+      'that file type is not allowed in this bucket. Allowed MIME types: image/png, image/jpeg.'
+    )
+  })
+
+  it('omits the list when the bucket allows everything', () => {
+    expect(describeUploadFailure({ status: 415, fallback: 'tus: unexpected response' })).toBe(
+      'that file type is not allowed in this bucket.'
+    )
+  })
+
+  it('explains a size rejection', () => {
+    expect(describeUploadFailure({ status: 413, fallback: 'tus: unexpected response' })).toBe(
+      'the file exceeds the bucket file size limit.'
+    )
+  })
+
+  it('falls back to the raw message for anything else', () => {
+    expect(describeUploadFailure({ status: 500, fallback: 'network down' })).toBe('network down')
+    expect(describeUploadFailure({ fallback: 'network down' })).toBe('network down')
+  })
+})
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.tsx b/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.tsx
index 98991c1125b..f0bb5338892 100644
--- a/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.tsx
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils.tsx
@@ -38,6 +38,15 @@ export function getPathAlongOpenedFolders(
  * Returns the path to the folder at the given index in the openedFolders array,
  * joining all folders from the root up to (but not including) the given index.
  */
+/** The object's full path within the bucket; a row only knows its leaf name and column. */
+export function getStorageItemPath(
+  state: Pick<StorageExplorerState, 'openedFolders'>,
+  item: { name: string; columnIndex: number }
+): string {
+  const folderPath = getPathAlongFoldersToIndex(state, item.columnIndex)
+  return folderPath.length > 0 ? `${folderPath}/${item.name}` : item.name
+}
+
 export function getPathAlongFoldersToIndex(
   state: Pick<StorageExplorerState, 'openedFolders'>,
   index: number
@@ -316,3 +325,26 @@ const readEntriesPromise = async (directoryReader: FileSystemDirectoryReader) =>
     console.error('readEntriesPromise error:', err)
   }
 }
+
+/**
+ * Storage rejects a write that breaks the bucket's own rules with a bare status and no
+ * usable message, so turn the ones a replace can hit into something actionable.
+ */
+export const describeUploadFailure = ({
+  status,
+  fallback,
+  allowedMimeTypes,
+}: {
+  status?: number
+  fallback: string
+  allowedMimeTypes?: string[] | null
+}) => {
+  if (status === 415) {
+    const allowed = allowedMimeTypes?.length
+      ? ` Allowed MIME types: ${allowedMimeTypes.join(', ')}.`
+      : ''
+    return `that file type is not allowed in this bucket.${allowed}`
+  }
+  if (status === 413) return 'the file exceeds the bucket file size limit.'
+  return fallback
+}
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/VersionHistory.tsx b/apps/studio/components/interfaces/Storage/StorageExplorer/VersionHistory.tsx
index c2b37652068..b378ee5ddf4 100644
--- a/apps/studio/components/interfaces/Storage/StorageExplorer/VersionHistory.tsx
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/VersionHistory.tsx
@@ -62,8 +62,8 @@ const VersionFateLabel = ({ fate }: { fate: VersionFate }) => {
             Queued to expire
           </TooltipTrigger>
           <TooltipContent side="bottom" className="max-w-64">
-            Matches the lifecycle policy and will be permanently deleted, which can take up to 24
-            hours.
+            Matches the lifecycle policy and will be permanently deleted. This action can take up to
+            24 hours.
           </TooltipContent>
         </Tooltip>
       )
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/pickFile.test.ts b/apps/studio/components/interfaces/Storage/StorageExplorer/pickFile.test.ts
new file mode 100644
index 00000000000..183842fc52f
--- /dev/null
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/pickFile.test.ts
@@ -0,0 +1,79 @@
+import { describe, expect, it, vi } from 'vitest'
+
+import { pickFile } from './pickFile'
+
+/** Captures the input `pickFile` creates, and whether `click()` happened synchronously. */
+const interceptInput = () => {
+  const created = { input: undefined as HTMLInputElement | undefined, clickedSync: false }
+  const realCreateElement = document.createElement.bind(document)
+
+  vi.spyOn(document, 'createElement').mockImplementation((tagName: string) => {
+    const element = realCreateElement(tagName)
+    if (tagName === 'input') {
+      created.input = element as HTMLInputElement
+      element.click = () => {
+        created.clickedSync = true
+      }
+    }
+    return element
+  })
+
+  return created
+}
+
+const setFiles = (input: HTMLInputElement, files: File[]) => {
+  Object.defineProperty(input, 'files', { value: files, configurable: true })
+}
+
+describe('pickFile', () => {
+  it('opens the picker synchronously, so the user gesture is not lost', () => {
+    const created = interceptInput()
+
+    void pickFile()
+
+    expect(created.clickedSync).toBe(true)
+    vi.restoreAllMocks()
+  })
+
+  it('resolves with the chosen file', async () => {
+    const created = interceptInput()
+    const pending = pickFile()
+    const file = new File(['hello'], 'avatar.png', { type: 'image/png' })
+
+    setFiles(created.input!, [file])
+    created.input!.dispatchEvent(new Event('change'))
+
+    await expect(pending).resolves.toBe(file)
+    vi.restoreAllMocks()
+  })
+
+  it('resolves undefined when the picker is dismissed', async () => {
+    const created = interceptInput()
+    const pending = pickFile()
+
+    created.input!.dispatchEvent(new Event('cancel'))
+
+    await expect(pending).resolves.toBeUndefined()
+    vi.restoreAllMocks()
+  })
+
+  it('resolves undefined when the picker closes with no selection', async () => {
+    const created = interceptInput()
+    const pending = pickFile()
+
+    setFiles(created.input!, [])
+    created.input!.dispatchEvent(new Event('change'))
+
+    await expect(pending).resolves.toBeUndefined()
+    vi.restoreAllMocks()
+  })
+
+  it('passes an accept filter through to the input', () => {
+    const created = interceptInput()
+
+    void pickFile({ accept: 'image/*' })
+
+    expect(created.input!.accept).toBe('image/*')
+    vi.restoreAllMocks()
+  })
+})
diff --git a/apps/studio/components/interfaces/Storage/StorageExplorer/pickFile.ts b/apps/studio/components/interfaces/Storage/StorageExplorer/pickFile.ts
new file mode 100644
index 00000000000..c81fcc43baf
--- /dev/null
+++ b/apps/studio/components/interfaces/Storage/StorageExplorer/pickFile.ts
@@ -0,0 +1,16 @@
+/**
+ * Created and clicked synchronously to stay inside the user gesture, which Safari
+ * requires — so no hidden input driven from an effect.
+ */
+export const pickFile = ({ accept }: { accept?: string } = {}): Promise<File | undefined> =>
+  new Promise((resolve) => {
+    const input = document.createElement('input')
+    input.type = 'file'
+    if (accept) input.accept = accept
+
+    input.addEventListener('change', () => resolve(input.files?.[0]), { once: true })
+    // Not supported everywhere, so this is a cleanup path rather than the one resolve needs.
+    input.addEventListener('cancel', () => resolve(undefined), { once: true })
+
+    input.click()
+  })
diff --git a/apps/studio/state/storage-explorer.tsx b/apps/studio/state/storage-explorer.tsx
index 71f4f774a63..450a5a6a516 100644
--- a/apps/studio/state/storage-explorer.tsx
+++ b/apps/studio/state/storage-explorer.tsx
@@ -32,15 +32,20 @@ import {
 } from '@/components/interfaces/Storage/Storage.types'
 import {
   calculateTotalRemainingTime,
+  describeUploadFailure,
   EMPTY_FOLDER_PLACEHOLDER_FILE_NAME,
   formatFolderItems,
   formatTime,
   getFilesDataTransferItems,
   getPathAlongFoldersToIndex,
+  getStorageItemPath,
   sanitizeNameForDuplicateInColumn,
   validateFolderName,
 } from '@/components/interfaces/Storage/StorageExplorer/StorageExplorer.utils'
-import { fetchFileUrl } from '@/components/interfaces/Storage/StorageExplorer/useFetchFileUrlQuery'
+import {
+  fetchFileUrl,
+  fileUrlKey,
+} from '@/components/interfaces/Storage/StorageExplorer/useFetchFileUrlQuery'
 import { getStoragePreference } from '@/components/interfaces/Storage/StorageExplorer/useStoragePreference'
 import { convertFromBytes } from '@/components/interfaces/Storage/StorageSettings/StorageSettings.utils'
 import { InlineLink } from '@/components/ui/InlineLink'
@@ -54,6 +59,7 @@ import { signBucketObjects } from '@/data/storage/bucket-object-sign-mutation'
 import { listBucketObjects, StorageObject } from '@/data/storage/bucket-objects-list-mutation'
 import { deleteBucketPrefix } from '@/data/storage/bucket-prefix-delete-mutation'
 import type { Bucket } from '@/data/storage/buckets-query'
+import { storageKeys } from '@/data/storage/keys'
 import { moveStorageObject } from '@/data/storage/object-move-mutation'
 import { useSelectedProjectQuery } from '@/hooks/misc/useSelectedProject'
 import { PROJECT_STATUS } from '@/lib/constants'
@@ -1503,6 +1509,82 @@ export function createStorageExplorerState({
       state.setSelectedItemsToMove([])
     },
 
+    /**
+     * Overwrites an object in place, which on a versioned bucket is what creates a new
+     * version. Not `uploadFiles`: that renames rather than overwrites on a name clash.
+     */
+    replaceFile: async ({ file, item }: { file: File; item: StorageItemWithColumn }) => {
+      const path = getStorageItemPath(state, item)
+      const toastId = toast.loading(`Uploading a new version of ${item.name}...`)
+
+      state.updateRowStatus({
+        name: item.name,
+        status: STORAGE_ROW_STATUS.LOADING,
+        columnIndex: item.columnIndex,
+      })
+
+      try {
+        await new Promise<void>((resolve, reject) => {
+          const upload = new tus.Upload(file, {
+            endpoint: state.resumableUploadUrl,
+            retryDelays: [0, 200, 500, 1500, 3000, 5000],
+            // Without upsert the write is rejected as a conflict: the path exists.
+            headers: { 'x-source': 'supabase-dashboard', 'x-upsert': 'true' },
+            uploadDataDuringCreation: true,
+            removeFingerprintOnSuccess: true,
+            metadata: {
+              bucketName: state.selectedBucket.name,
+              objectName: path,
+              contentType: file.type || 'application/octet-stream',
+              cacheControl: '3600',
+            },
+            onBeforeRequest: async (req) => {
+              const { apiKey } = await getOrRefreshTemporaryApiKey(state.projectRef)
+              req.setHeader('apikey', apiKey)
+              if (!IS_PLATFORM) req.setHeader('Authorization', `Bearer ${apiKey}`)
+            },
+            onError: (error) => reject(error),
+            onSuccess: () => resolve(),
+          })
+
+          // No `findPreviousUploads`: a resumed upload would write the wrong file's bytes.
+          upload.start()
+        })
+
+        toast.success(`Uploaded a new version of ${item.name}`, { id: toastId })
+        await state.refetchAllOpenedFolders()
+        await Promise.all([
+          getQueryClient().invalidateQueries({
+            queryKey: storageKeys.objectVersions(state.projectRef, state.selectedBucket.id, path),
+          }),
+          // The preview URL is cached for a week against the path, so without this the
+          // panel keeps rendering the bytes from before the replace.
+          getQueryClient().invalidateQueries({
+            queryKey: fileUrlKey({
+              projectRef: state.projectRef,
+              isBucketPublic: state.selectedBucket.public,
+              bucketId: state.selectedBucket.id,
+              path,
+            }),
+          }),
+        ])
+      } catch (error) {
+        const status =
+          error instanceof tus.DetailedError ? error.originalResponse?.getStatus() : undefined
+        const reason = describeUploadFailure({
+          status,
+          fallback: error instanceof Error ? error.message : 'the upload failed.',
+          allowedMimeTypes: state.selectedBucket.allowed_mime_types,
+        })
+        toast.error(`Failed to upload a new version of ${item.name}: ${reason}`, { id: toastId })
+        state.updateRowStatus({
+          name: item.name,
+          status: STORAGE_ROW_STATUS.READY,
+          columnIndex: item.columnIndex,
+        })
+      }
+    },
+
     deleteFiles: async ({
       files,
       isDeleteFolder = false,