diff --git a/.prettierignore b/.prettierignore
index c0d99ece4f..b95078792c 100644
--- a/.prettierignore
+++ b/.prettierignore
@@ -49,4 +49,5 @@ src/main/webapp/fonts/*
 # If using jenv for JDK management
 /.java-version
 
-
+# Ignore e2e mock data files
+/e2e/data/*.csv
diff --git a/e2e/data/test_file.csv b/e2e/data/test_file.csv
new file mode 100644
index 0000000000..68f742262b
--- /dev/null
+++ b/e2e/data/test_file.csv
@@ -0,0 +1,4 @@
+first,second,third
+1,one,true
+2,two,false
+3,three,true
diff --git a/e2e/data/test_file2.csv b/e2e/data/test_file2.csv
new file mode 100644
index 0000000000..02f17b0b95
--- /dev/null
+++ b/e2e/data/test_file2.csv
@@ -0,0 +1,4 @@
+first,second,third,four
+1,one,true,a
+2,two,false,b
+3,three,true,c
diff --git a/e2e/files.spec.ts b/e2e/files.spec.ts
index 75fd3ba28e..0f07ff616b 100644
--- a/e2e/files.spec.ts
+++ b/e2e/files.spec.ts
@@ -1,4 +1,5 @@
 import { Page, expect, test } from '@playwright/test'
+import path from 'path'
 import { testAuth } from './fixtures/authenticatedUserPages'
 import {
   createFile,
@@ -7,8 +8,14 @@ import {
   deleteProject,
   entityUrlPathname,
   generateEntityName,
+  getEntityFileHandleId,
+  getEntityIdFromPathname,
 } from './helpers/entities'
-import { getAccessTokenFromCookie, getAdminPAT } from './helpers/testUser'
+import {
+  dismissAlert,
+  getAccessTokenFromCookie,
+  getAdminPAT,
+} from './helpers/testUser'
 import { Project } from './helpers/types'
 import { userConfigs } from './helpers/userConfig'
 import { waitForInitialPageLoad } from './helpers/utils'
@@ -18,11 +25,13 @@ const expectFilePageLoaded = async (
   fileEntityId: string,
   page: Page,
 ) => {
-  await page.waitForURL(entityUrlPathname(fileEntityId))
-  await expect(page.getByText(`Discussion about ${fileName}`)).toBeVisible()
+  await testAuth.step('file page is loaded', async () => {
+    await page.waitForURL(entityUrlPathname(fileEntityId))
+    await expect(page.getByText(`Discussion about ${fileName}`)).toBeVisible()
 
-  await expect(page.getByText('Loading provenance...')).not.toBeVisible()
-  await expect(page.getByText(fileEntityId, { exact: true })).toBeVisible()
+    await expect(page.getByText('Loading provenance...')).not.toBeVisible()
+    await expect(page.getByText(fileEntityId, { exact: true })).toBeVisible()
+  })
 }
 
 const openFileSharingSettings = async (page: Page) => {
@@ -80,15 +89,6 @@ const confirmSharingSettings = async (
   )
 }
 
-const confirmAndClosePermissionsSavedAlert = async (page: Page) => {
-  const permissionsAlert = page.getByRole('alert').filter({
-    has: page.getByText('Permissions were successfully saved to Synapse'),
-  })
-  await expect(permissionsAlert).toBeVisible()
-  await permissionsAlert.getByRole('button').click()
-  await expect(permissionsAlert).not.toBeVisible()
-}
-
 const saveFileSharingSettings = async (page: Page) => {
   const saveButton = page.getByRole('button', { name: 'Save' })
   await saveButton.click()
@@ -99,7 +99,62 @@ const saveFileSharingSettings = async (page: Page) => {
     page.getByRole('heading', { name: 'File Sharing Settings' }),
   ).not.toBeVisible()
 
-  await confirmAndClosePermissionsSavedAlert(page)
+  await dismissAlert(page, 'Permissions were successfully saved to Synapse')
+}
+
+const uploadFile = async (
+  page: Page,
+  filePath: string,
+  uploadType: 'initialUpload' | 'newVersion',
+) => {
+  await testAuth.step('open file upload modal', async () => {
+    const uploadButtonText =
+      uploadType === 'initialUpload'
+        ? 'Upload or Link to a File'
+        : 'Upload a New Version of File'
+    await page.getByRole('button', { name: uploadButtonText }).click()
+  })
+
+  await testAuth.step('choose file', async () => {
+    const fileChooserPromise = page.waitForEvent('filechooser')
+    await page.getByRole('button', { name: 'Browse...' }).click()
+    if (uploadType === 'initialUpload') {
+      await page
+        .getByRole('menu')
+        .getByRole('link')
+        .filter({ hasText: 'Files' })
+        .click()
+    }
+    const fileChooser = await fileChooserPromise
+    await fileChooser.setFiles(path.join(__dirname, filePath))
+  })
+
+  await testAuth.step('wait for file upload modal to close', async () => {
+    await expect(page.getByText('Initializing......')).not.toBeVisible()
+    await expect(
+      page.getByRole('heading', { name: 'Upload or Link to File' }),
+    ).not.toBeVisible()
+  })
+
+  await testAuth.step('ensure there was not an upload error', async () => {
+    await expect(
+      page.getByRole('heading', { name: 'Upload Error' }),
+    ).not.toBeVisible()
+  })
+}
+
+const dismissFileUploadAlert = async (page: Page) => {
+  await testAuth.step('dismiss file upload alert', async () => {
+    await dismissAlert(page, 'File successfully uploaded')
+  })
+}
+
+const getFileMD5 = async (page: Page) => {
+  return await testAuth.step('get file MD5', async () => {
+    const row = page.getByRole('row').filter({ hasText: 'MD5' })
+    expect(row.getByRole('cell')).toHaveCount(2)
+    return row.getByRole('cell').filter({ hasNotText: 'MD5' }).textContent()
+  })
 }
 
 let userProject: Project
@@ -282,4 +337,210 @@ test.describe('Files', () => {
       })
     },
   )
+
+  testAuth(
+    'should create and delete a file',
+    async ({ userPage, browserName }) => {
+      test.fail(
+        browserName === 'webkit',
+        `Playwright is not preserving the File's lastModified time in webkit, so 
+        file upload fails because it seems like the file was modified during 
+        upload. See https://github.com/microsoft/playwright/issues/27452. Fix 
+        planned for Playwright v1.40.`,
+      )
+
+      const fileName = 'test_file.csv'
+      const filePath = `data/${fileName}`
+      const updatedFilePath = `data/test_file2.csv`
+
+      await testAuth.step('go to files tab', async () => {
+        await userPage.goto(entityUrlPathname(userProject.id))
+        await waitForInitialPageLoad(userPage)
+        await expect(
+          userPage.getByRole('heading', { name: userProject.name }),
+        ).toBeVisible()
+        await userPage.getByRole('link', { name: 'Files', exact: true }).click()
+      })
+
+      await testAuth.step('upload file', async () => {
+        await uploadFile(userPage, filePath, 'initialUpload')
+        await dismissFileUploadAlert(userPage)
+      })
+
+      const fileLink = await testAuth.step('get link to file', async () => {
+        const fileLink = userPage.getByRole('link', { name: fileName })
+        await expect(fileLink).toBeVisible()
+        return fileLink
+      })
+
+      const { fileEntityId } = await testAuth.step(
+        'get fileEntityId',
+        async () => {
+          const fileLinkHref = await fileLink.getAttribute('href')
+          expect(fileLinkHref).not.toBeNull()
+
+          const fileEntityId = getEntityIdFromPathname(fileLinkHref!)
+          expect(fileEntityId).not.toBe('')
+
+          return { fileEntityId }
+        },
+      )
+
+      const md5v1 = await testAuth.step('view file', async () => {
+        await fileLink.click()
+        await expectFilePageLoaded(fileName, fileEntityId, userPage)
+        return await getFileMD5(userPage)
+      })
+
+      await testAuth.step('re-upload file', async () => {
+        await uploadFile(userPage, filePath, 'newVersion')
+        await expectFilePageLoaded(fileName, fileEntityId, userPage)
+      })
+
+      await testAuth.step(
+        'confirm re-upload did not change md5 or version',
+        async () => {
+          const md5reupload = await getFileMD5(userPage)
+          expect(md5v1).toEqual(md5reupload)
+          await expect(userPage.getByText('V1 (Current)')).toBeVisible()
+        },
+      )
+
+      // Upload success alert intermittently appears when re-uploading the same file
+      await testAuth.step(
+        'dismiss file upload alert for re-uploaded file, if visible',
+        async () => {
+          if (
+            await userPage.getByText('File successfully uploaded').isVisible()
+          ) {
+            await dismissFileUploadAlert(userPage)
+          }
+        },
+      )
+
+      await testAuth.step('upload a new file', async () => {
+        await uploadFile(userPage, updatedFilePath, 'newVersion')
+        await expectFilePageLoaded(fileName, fileEntityId, userPage)
+        await dismissFileUploadAlert(userPage)
+      })
+
+      await testAuth.step(
+        'confirm uploading new file changed md5 and version',
+        async () => {
+          const md5v2 = await getFileMD5(userPage)
+          expect(md5v1).not.toEqual(md5v2)
+          await expect(userPage.getByText('V2 (Current)')).toBeVisible()
+        },
+      )
+
+      await testAuth.step(
+        'add associated fileHandleIds to cleanup list',
+        async () => {
+          const fileHandleIdV1 = await getEntityFileHandleId(
+            userPage,
+            getAdminPAT(),
+            fileEntityId,
+            1,
+          )
+          const fileHandleIdV2 = await getEntityFileHandleId(
+            userPage,
+            getAdminPAT(),
+            fileEntityId,
+            2,
+          )
+          fileHandleIds.push(fileHandleIdV1)
+          fileHandleIds.push(fileHandleIdV2)
+        },
+      )
+
+      await testAuth.step('move file to trash can', async () => {
+        await testAuth.step('delete file', async () => {
+          await userPage.getByRole('button', { name: 'File Tools' }).click()
+          await userPage.getByRole('menuitem', { name: 'Delete File' }).click()
+        })
+
+        await testAuth.step('confirm deletion', async () => {
+          await expect(
+            userPage.getByRole('heading', { name: 'Confirm Deletion' }),
+          ).toBeVisible()
+          await expect(
+            userPage.getByText(
+              `Are you sure you want to delete File "${fileName}"?`,
+            ),
+          ).toBeVisible()
+          await expect(
+            userPage.getByRole('button', { name: 'Cancel' }),
+          ).toBeVisible()
+
+          await userPage.getByRole('button', { name: 'Delete' }).click()
+        })
+
+        await testAuth.step('confirm that file was deleted', async () => {
+          await userPage.waitForURL(
+            `${entityUrlPathname(userProject.id)}/files/`,
+          )
+
+          await expect(
+            userPage.getByRole('heading', { name: 'Files' }),
+          ).toBeVisible()
+          await expect(
+            userPage.getByRole('link', { name: fileName }),
+          ).not.toBeVisible()
+
+          await dismissAlert(userPage, 'The File was successfully deleted.')
+        })
+      })
+
+      await testAuth.step('remove file from trash can', async () => {
+        await testAuth.step('go to trash can', async () => {
+          await userPage.getByLabel('Trash Can').click()
+
+          const trashCanHeading = userPage.getByRole('heading', {
+            name: 'Trash Can',
+          })
+          await expect(trashCanHeading).toBeVisible()
+
+          // click on heading, so tooltip on trash can nav button is hidden
+          await trashCanHeading.click()
+        })
+
+        await testAuth.step('remove file from trash can', async () => {
+          const fileCheckbox = userPage.getByRole('checkbox', {
+            name: `Select ${fileEntityId}`,
+          })
+          await expect(fileCheckbox).not.toBeChecked()
+
+          // Currently programmatically dispatching the click event
+          // because the following aren't working:
+          //  - await fileCheckbox.click() -> fails due to <div class="pageContent margin-top-60"> intercepting pointer events
+          //  - await fileCheckbox.click({force: true}) -> fails to actually check the checkbox
+          await fileCheckbox.dispatchEvent('click')
+
+          await expect(fileCheckbox).toBeChecked()
+
+          await userPage
+            .getByRole('button', { name: 'Delete Selected' })
+            .click()
+        })
+
+        await testAuth.step('confirm removal from trash can', async () => {
+          await expect(
+            userPage.getByText('Delete selected items from your Trash?'),
+          ).toBeVisible()
+          await userPage.getByRole('button', { name: 'Delete' }).click()
+        })
+
+        await testAuth.step(
+          'confirm that file was removed from trash can',
+          async () => {
+            await expect(userPage.getByText(fileName)).not.toBeVisible()
+            await expect(userPage.getByText(fileEntityId)).not.toBeVisible()
+            await expect(
+              userPage.getByText('Trash Can is currently empty.'),
+            ).toBeVisible()
+          },
+        )
+      })
+    },
+  )
 })
diff --git a/e2e/helpers/entities.ts b/e2e/helpers/entities.ts
index 11317b1e33..7c5e0de55a 100644
--- a/e2e/helpers/entities.ts
+++ b/e2e/helpers/entities.ts
@@ -8,8 +8,20 @@ export function generateEntityName(entityType: 'project' | 'folder' | 'file') {
   return `swc-e2e-${entityType}-entity-${uuidv4()}`
 }
 
+const entityHashBang = '#!Synapse'
+
 export function entityUrlPathname(entityId: string) {
-  return `/#!Synapse:${entityId}`
+  return `/${entityHashBang}:${entityId}`
+}
+
+export function getEntityIdFromPathname(pathname: string) {
+  if (!pathname.includes(entityHashBang)) {
+    return ''
+  }
+
+  return pathname
+    .replace(new RegExp(`.*${entityHashBang}:`), '')
+    .replace(/\/.*/, '')
 }
 
 export async function createProject(
@@ -130,6 +142,16 @@ export async function getEntity(
   return entity
 }
 
+export async function getEntityFileHandleId(
+  page: Page,
+  accessToken: string | undefined = undefined,
+  entityId: string,
+  versionNumber?: string | number,
+) {
+  const fileEntity = await getEntity(page, accessToken, entityId, versionNumber)
+  return fileEntity.dataFileHandleId as string
+}
+
 // https://rest-docs.synapse.org/rest/DELETE/entity/id.html
 // Note: not using SRC.deleteEntity, because it does not expose the skipTrashCan option
 export async function deleteEntity(
diff --git a/e2e/helpers/testUser.ts b/e2e/helpers/testUser.ts
index 7c59058dfc..a0839c1ad4 100644
--- a/e2e/helpers/testUser.ts
+++ b/e2e/helpers/testUser.ts
@@ -141,3 +141,10 @@ export async function getUserIdFromLocalStorage(page: Page) {
 export async function acceptSiteCookies(page: Page) {
   await page.getByRole('button', { name: 'Accept and continue' }).click()
 }
+
+export const dismissAlert = async (page: Page, alertText: string) => {
+  const alert = page.getByRole('alert').filter({ hasText: alertText })
+  expect(alert).toBeVisible()
+  await alert.getByRole('button', { name: 'Close' }).click()
+  await expect(alert).not.toBeVisible()
+}
diff --git a/e2e/helpers/userConfig.ts b/e2e/helpers/userConfig.ts
index 40d4a1fdca..55ffa780b6 100644
--- a/e2e/helpers/userConfig.ts
+++ b/e2e/helpers/userConfig.ts
@@ -11,7 +11,7 @@ export type UserPrefixes = (typeof userPrefixes)[number]
 const generateUserName = (prefix: string) => {
   // uncomment to use static username for troubleshooting:
   // ...and ensure that usernames are unique per worker
-  // return `${prefix}-${process.env.TEST_PARALLEL_INDEX}`
+  // return `local-${prefix}-${process.env.TEST_PARALLEL_INDEX}`
 
   return `${prefix}-${uuidv4()}`
 }