diff --git a/e2e/playwright/file-tree.spec.ts b/e2e/playwright/file-tree.spec.ts
new file mode 100644
index 000000000..c6eb0e6b7
--- /dev/null
+++ b/e2e/playwright/file-tree.spec.ts
@@ -0,0 +1,204 @@
+import { test, expect } from '@playwright/test'
+import * as fsp from 'fs/promises'
+import { getUtils, setup, setupElectron, tearDown } from './test-utils'
+
+test.beforeEach(async ({ context, page }) => {
+  await setup(context, page)
+})
+
+test.afterEach(async ({ page }, testInfo) => {
+  await tearDown(page, testInfo)
+})
+
+test.describe('when using the file tree to', () => {
+  const fromFile = 'main.kcl'
+  const toFile = 'hello.kcl'
+
+  test(
+    `rename ${fromFile} to ${toFile}, and doesn't crash on reload and settings load`,
+    { tag: '@electron' },
+    async ({ browser: _ }, testInfo) => {
+      const { electronApp, page } = await setupElectron({
+        testInfo,
+        folderSetupFn: async () => {},
+      })
+
+      const {
+        panesOpen,
+        createAndSelectProject,
+        pasteCodeInEditor,
+        renameFile,
+        editorTextMatches,
+      } = await getUtils(page, test)
+
+      await page.setViewportSize({ width: 1200, height: 500 })
+      page.on('console', console.log)
+
+      await panesOpen(['files', 'code'])
+
+      await createAndSelectProject('project-000')
+
+      // File the main.kcl with contents
+      const kclCube = await fsp.readFile(
+        'src/wasm-lib/tests/executor/inputs/cube.kcl',
+        'utf-8'
+      )
+      await pasteCodeInEditor(kclCube)
+
+      await renameFile(fromFile, toFile)
+      await page.reload()
+
+      await test.step('Postcondition: editor has same content as before the rename', async () => {
+        await editorTextMatches(kclCube)
+      })
+
+      await test.step('Postcondition: opening and closing settings works', async () => {
+        const settingsOpenButton = page.getByRole('link', {
+          name: 'settings Settings',
+        })
+        const settingsCloseButton = page.getByTestId('settings-close-button')
+        await settingsOpenButton.click()
+        await settingsCloseButton.click()
+      })
+
+      await electronApp.close()
+    }
+  )
+
+  test(
+    `create many new untitled files they increment their names`,
+    { tag: '@electron' },
+    async ({ browser: _ }, testInfo) => {
+      const { electronApp, page } = await setupElectron({
+        testInfo,
+        folderSetupFn: async () => {},
+      })
+
+      const { panesOpen, createAndSelectProject, createNewFile } =
+        await getUtils(page, test)
+
+      await page.setViewportSize({ width: 1200, height: 500 })
+      page.on('console', console.log)
+
+      await panesOpen(['files'])
+
+      await createAndSelectProject('project-000')
+
+      await createNewFile('')
+      await createNewFile('')
+      await createNewFile('')
+      await createNewFile('')
+      await createNewFile('')
+
+      await test.step('Postcondition: there are 5 new Untitled-*.kcl files', async () => {
+        await expect(
+          page
+            .locator('[data-testid="file-pane-scroll-container"] button')
+            .filter({ hasText: /Untitled[-]?[0-5]?/ })
+        ).toHaveCount(5)
+      })
+
+      await electronApp.close()
+    }
+  )
+
+  test(
+    'create a new file with the same name as an existing file cancels the operation',
+    { tag: '@electron' },
+    async ({ browser: _ }, testInfo) => {
+      const { electronApp, page } = await setupElectron({
+        testInfo,
+        folderSetupFn: async () => {},
+      })
+
+      const {
+        panesOpen,
+        createAndSelectProject,
+        pasteCodeInEditor,
+        createNewFileAndSelect,
+        renameFile,
+        selectFile,
+        editorTextMatches,
+      } = await getUtils(page, test)
+
+      await page.setViewportSize({ width: 1200, height: 500 })
+      page.on('console', console.log)
+
+      await panesOpen(['files', 'code'])
+
+      await createAndSelectProject('project-000')
+      // File the main.kcl with contents
+      const kclCube = await fsp.readFile(
+        'src/wasm-lib/tests/executor/inputs/cube.kcl',
+        'utf-8'
+      )
+      await pasteCodeInEditor(kclCube)
+
+      const kcl1 = 'main.kcl'
+      const kcl2 = '2.kcl'
+
+      await createNewFileAndSelect(kcl2)
+      const kclCylinder = await fsp.readFile(
+        'src/wasm-lib/tests/executor/inputs/cylinder.kcl',
+        'utf-8'
+      )
+      await pasteCodeInEditor(kclCylinder)
+
+      await renameFile(kcl2, kcl1)
+
+      await test.step(`Postcondition: ${kcl1} still has the original content`, async () => {
+        await selectFile(kcl1)
+        await editorTextMatches(kclCube)
+      })
+
+      await test.step(`Postcondition: ${kcl2} still exists with the original content`, async () => {
+        await selectFile(kcl2)
+        await editorTextMatches(kclCylinder)
+      })
+
+      await electronApp.close()
+    }
+  )
+
+  test(
+    'deleting all files recreates a default main.kcl with no code',
+    { tag: '@electron' },
+    async ({ browser: _ }, testInfo) => {
+      const { electronApp, page } = await setupElectron({
+        testInfo,
+        folderSetupFn: async () => {},
+      })
+
+      const {
+        panesOpen,
+        createAndSelectProject,
+        pasteCodeInEditor,
+        deleteFile,
+        editorTextMatches,
+      } = await getUtils(page, test)
+
+      await page.setViewportSize({ width: 1200, height: 500 })
+      page.on('console', console.log)
+
+      await panesOpen(['files', 'code'])
+
+      await createAndSelectProject('project-000')
+      // File the main.kcl with contents
+      const kclCube = await fsp.readFile(
+        'src/wasm-lib/tests/executor/inputs/cube.kcl',
+        'utf-8'
+      )
+      await pasteCodeInEditor(kclCube)
+
+      const kcl1 = 'main.kcl'
+
+      await deleteFile(kcl1)
+
+      await test.step(`Postcondition: ${kcl1} is recreated but has no content`, async () => {
+        await editorTextMatches('')
+      })
+
+      await electronApp.close()
+    }
+  )
+})
diff --git a/e2e/playwright/test-utils.ts b/e2e/playwright/test-utils.ts
index 9d8991feb..6f43ad933 100644
--- a/e2e/playwright/test-utils.ts
+++ b/e2e/playwright/test-utils.ts
@@ -511,10 +511,7 @@ export async function getUtils(page: Page, test_?: typeof test) {
 
     editorTextMatches: async (code: string) => {
       const editor = page.locator(editorSelector)
-      const editorText = await editor.textContent()
-      return expect(util.toNormalizedCode(editorText || '')).toBe(
-        util.toNormalizedCode(code)
-      )
+      return expect(editor).toHaveText(code, { useInnerText: true })
     },
 
     pasteCodeInEditor: async (code: string) => {
@@ -532,18 +529,62 @@ export async function getUtils(page: Page, test_?: typeof test) {
       })
     },
 
+    createNewFile: async (name: string) => {
+      return test?.step(`Create a file named ${name}`, async () => {
+        await page.getByTestId('create-file-button').click()
+        await page.getByTestId('file-rename-field').fill(name)
+        await page.keyboard.press('Enter')
+      })
+    },
+
+    selectFile: async (name: string) => {
+      return test?.step(`Select ${name}`, async () => {
+        await page
+          .locator('[data-testid="file-pane-scroll-container"] button')
+          .filter({ hasText: name })
+          .click()
+      })
+    },
+
     createNewFileAndSelect: async (name: string) => {
       return test?.step(`Create a file named ${name}, select it`, async () => {
         await page.getByTestId('create-file-button').click()
         await page.getByTestId('file-rename-field').fill(name)
         await page.keyboard.press('Enter')
         await page
-          .getByTestId('file-pane-scroll-container')
+          .locator('[data-testid="file-pane-scroll-container"] button')
           .filter({ hasText: name })
           .click()
       })
     },
 
+    renameFile: async (fromName: string, toName: string) => {
+      return test?.step(`Rename ${fromName} to ${toName}`, async () => {
+        await page
+          .locator('[data-testid="file-pane-scroll-container"] button')
+          .filter({ hasText: fromName })
+          .click({ button: 'right' })
+        await page.getByTestId('context-menu-rename').click()
+        await page.getByTestId('file-rename-field').fill(toName)
+        await page.keyboard.press('Enter')
+        await page
+          .locator('[data-testid="file-pane-scroll-container"] button')
+          .filter({ hasText: toName })
+          .click()
+      })
+    },
+
+    deleteFile: async (name: string) => {
+      return test?.step(`Delete ${name}`, async () => {
+        await page
+          .locator('[data-testid="file-pane-scroll-container"] button')
+          .filter({ hasText: name })
+          .click({ button: 'right' })
+        await page.getByTestId('context-menu-delete').click()
+        await page.getByTestId('delete-confirmation').click()
+      })
+    },
+
     panesOpen: async (paneIds: PaneId[]) => {
       return test?.step(`Setting ${paneIds} panes to be open`, async () => {
         await page.addInitScript(
diff --git a/e2e/playwright/text-to-cad-tests.spec.ts b/e2e/playwright/text-to-cad-tests.spec.ts
index 3a22036a9..8dc2b6d7b 100644
--- a/e2e/playwright/text-to-cad-tests.spec.ts
+++ b/e2e/playwright/text-to-cad-tests.spec.ts
@@ -1,11 +1,5 @@
 import { test, expect, Page } from '@playwright/test'
-import {
-  getUtils,
-  setup,
-  tearDown,
-  setupElectron,
-  createProjectAndRenameIt,
-} from './test-utils'
+import { getUtils, setup, tearDown, setupElectron } from './test-utils'
 import { join } from 'path'
 import fs from 'fs'
 
@@ -698,13 +692,16 @@ test(
   async ({ browserName }, testInfo) => {
     const { electronApp, page, dir } = await setupElectron({ testInfo })
     const fileExists = () =>
-      fs.existsSync(join(dir, 'test-000', 'lego-2x4.kcl'))
+      fs.existsSync(join(dir, 'project-000', 'lego-2x4.kcl'))
+
+    const { createAndSelectProject, panesOpen } = await getUtils(page, test)
 
     await page.setViewportSize({ width: 1200, height: 500 })
 
+    await panesOpen(['code', 'files'])
+
     // Create and navigate to the project
-    await createProjectAndRenameIt({ name: 'test-000', page })
-    await page.getByTestId('project-link').click()
+    await createAndSelectProject('project-000')
 
     // Wait for Start Sketch otherwise you will not have access Text-to-CAD command
     await expect(
@@ -713,10 +710,6 @@ test(
       timeout: 20_000,
     })
 
-    // Open the files pane
-    const filesPaneButton = page.getByTestId('files-pane-button')
-    await filesPaneButton.click()
-
     await test.step(`Test file creation`, async () => {
       await sendPromptFromCommandBar(page, 'lego 2x4')
       // File is considered created if it shows up in the Project Files pane
diff --git a/playwright-electron.config.ts b/playwright-electron.config.ts
deleted file mode 100644
index 8eeaed1af..000000000
--- a/playwright-electron.config.ts
+++ /dev/null
@@ -1,31 +0,0 @@
-import { defineConfig, devices } from '@playwright/test'
-import dotenv from 'dotenv'
-
-/**
- * See https://playwright.dev/docs/test-configuration.
- */
-export default defineConfig({
-  timeout: 120_000, // override the default 30s timeout
-  testDir: './e2e/playwright',
-  /* Run tests in files in parallel */
-  fullyParallel: true,
-  /* Fail the build on CI if you accidentally left test.only in the source code. */
-  forbidOnly: !!process.env.CI,
-  /* Do not retry */
-  retries: process.env.CI ? 0 : 0,
-  /* Different amount of parallelism on CI and local. */
-  workers: process.env.CI ? 1 : 4,
-  /* Reporter to use. See https://playwright.dev/docs/test-reporters */
-  reporter: [
-    [process.env.CI ? 'dot' : 'list'],
-    ['json', { outputFile: './test-results/report.json' }],
-    ['html'],
-  ],
-  /* Shared settings for all the projects below. See https://playwright.dev/docs/api/class-testoptions. */
-  use: {
-    /* Collect trace when retrying the failed test. See https://playwright.dev/docs/trace-viewer */
-    trace: 'retain-on-failure',
-    actionTimeout: 15000,
-    screenshot: 'only-on-failure',
-  },
-})
diff --git a/src/components/ContextMenu.tsx b/src/components/ContextMenu.tsx
index b57c6aa7f..05722cca4 100644
--- a/src/components/ContextMenu.tsx
+++ b/src/components/ContextMenu.tsx
@@ -135,16 +135,15 @@ interface ContextMenuItemProps {
   icon?: ActionIconProps['icon']
   onClick?: () => void
   hotkey?: string
+  'data-testid'?: string
 }
 
-export function ContextMenuItem({
-  children,
-  icon,
-  onClick,
-  hotkey,
-}: ContextMenuItemProps) {
+export function ContextMenuItem(props: ContextMenuItemProps) {
+  const { children, icon, onClick, hotkey } = props
+
   return (
     <button
+      data-testid={props['data-testid']}
       className="flex items-center gap-2 py-1 px-2 cursor-pointer hover:bg-chalkboard-20 dark:hover:bg-chalkboard-80 border-none text-left"
       onClick={onClick}
     >
diff --git a/src/components/FileMachineProvider.tsx b/src/components/FileMachineProvider.tsx
index 0375fe291..af45d52e5 100644
--- a/src/components/FileMachineProvider.tsx
+++ b/src/components/FileMachineProvider.tsx
@@ -16,7 +16,11 @@ import {
 import { useCommandsContext } from 'hooks/useCommandsContext'
 import { fileMachine } from 'machines/fileMachine'
 import { isDesktop } from 'lib/isDesktop'
-import { DEFAULT_FILE_NAME, FILE_EXT } from 'lib/constants'
+import {
+  DEFAULT_FILE_NAME,
+  DEFAULT_PROJECT_KCL_FILE,
+  FILE_EXT,
+} from 'lib/constants'
 import { getProjectInfo } from 'lib/desktop'
 import { getNextDirName, getNextFileName } from 'lib/desktopFS'
 
@@ -167,6 +171,25 @@ export const FileMachineProvider = ({
           name
         )
 
+        // no-op
+        if (oldPath === newPath) {
+          return {
+            message: `Old is the same as new.`,
+            newPath,
+            oldPath,
+          }
+        }
+
+        // if there are any siblings with the same name, report error.
+        const entries = await window.electron.readdir(
+          window.electron.path.dirname(newPath)
+        )
+        for (let entry of entries) {
+          if (entry === newName) {
+            return Promise.reject(new Error('Filename already exists.'))
+          }
+        }
+
         window.electron.rename(oldPath, newPath)
 
         if (!file) {
@@ -209,6 +232,27 @@ export const FileMachineProvider = ({
             .catch((e) => console.error('Error deleting file', e))
         }
 
+        // If there are no more files at all in the project, create a main.kcl
+        // for when we navigate to the root.
+        if (!project?.path) {
+          return Promise.reject(new Error('Project path not set.'))
+        }
+
+        const entries = await window.electron.readdir(project.path)
+        const hasKclEntries =
+          entries.filter((e: string) => e.endsWith('.kcl')).length !== 0
+        if (!hasKclEntries) {
+          await window.electron.writeFile(
+            window.electron.path.join(project.path, DEFAULT_PROJECT_KCL_FILE),
+            ''
+          )
+          // Refresh the route selected above because it's possible we're on
+          // the same path on the navigate, which doesn't cause anything to
+          // refresh, leaving a stale execution state.
+          navigate(0)
+          return
+        }
+
         // If we just deleted the current file or one of its parent directories,
         // navigate to the project root
         if (
diff --git a/src/components/FileTree.tsx b/src/components/FileTree.tsx
index 9c3acad3c..1b9b608c8 100644
--- a/src/components/FileTree.tsx
+++ b/src/components/FileTree.tsx
@@ -358,10 +358,18 @@ function FileTreeContextMenu({
     <ContextMenu
       menuTargetElement={itemRef}
       items={[
-        <ContextMenuItem onClick={onRename} hotkey="Enter">
+        <ContextMenuItem
+          data-testid="context-menu-rename"
+          onClick={onRename}
+          hotkey="Enter"
+        >
           Rename
         </ContextMenuItem>,
-        <ContextMenuItem onClick={onDelete} hotkey={metaKey + ' + Del'}>
+        <ContextMenuItem
+          data-testid="context-menu-delete"
+          onClick={onDelete}
+          hotkey={metaKey + ' + Del'}
+        >
           Delete
         </ContextMenuItem>,
       ]}
diff --git a/src/lang/modifyAst/addFillet.test.ts b/src/lang/modifyAst/addFillet.test.ts
index f1059b4a5..b72fd07f5 100644
--- a/src/lang/modifyAst/addFillet.test.ts
+++ b/src/lang/modifyAst/addFillet.test.ts
@@ -152,7 +152,7 @@ const extrude001 = extrude(-15, sketch001)`
       selectedSegmentSnippet,
       expectedExtrudeSnippet
     )
-  })
+  }, 5_000)
   it('should return the correct paths for a valid selection and extrusion in case of several extrusions and sketches', async () => {
     const code = `const sketch001 = startSketchOn('XY')
   |> startProfileAt([-30, 30], %)
diff --git a/src/lib/constants.ts b/src/lib/constants.ts
index a0ddeb962..3c7f2b7f3 100644
--- a/src/lib/constants.ts
+++ b/src/lib/constants.ts
@@ -8,6 +8,7 @@ export const MAX_PADDING = 7
  * This is available for users to edit as a setting.
  */
 export const DEFAULT_PROJECT_NAME = 'project-$nnn'
+export const DEFAULT_PROJECT_KCL_FILE = 'main.kcl'
 /** Name given the temporary "project" in the browser version of the app */
 export const BROWSER_PROJECT_NAME = 'browser'
 /** Name given the temporary file in the browser version of the app */
diff --git a/src/lib/routeLoaders.ts b/src/lib/routeLoaders.ts
index 079c8c6fc..67a50488f 100644
--- a/src/lib/routeLoaders.ts
+++ b/src/lib/routeLoaders.ts
@@ -90,12 +90,24 @@ export const fileLoader: LoaderFunction = async (
     let code = ''
 
     if (!urlObj.pathname.endsWith('/settings')) {
-      if (!currentFileName || !currentFilePath || !projectName) {
+      const fallbackFile = isDesktop()
+        ? (await getProjectInfo(projectPath)).default_file
+        : ''
+      let fileExists = isDesktop()
+      if (currentFilePath && fileExists) {
+        try {
+          await window.electron.stat(currentFilePath)
+        } catch (e) {
+          if (e === 'ENOENT') {
+            fileExists = false
+          }
+        }
+      }
+
+      if (!fileExists || !currentFileName || !currentFilePath || !projectName) {
         return redirect(
           `${PATHS.FILE}/${encodeURIComponent(
-            isDesktop()
-              ? (await getProjectInfo(projectPath)).default_file
-              : params.id + '/' + PROJECT_ENTRYPOINT
+            isDesktop() ? fallbackFile : params.id + '/' + PROJECT_ENTRYPOINT
           )}`
         )
       }