diff --git a/.circleci/config.yml b/.circleci/config.yml
index 49517d59e77f..63129f9e1b73 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -27,7 +27,7 @@ mainBuildFilters: &mainBuildFilters
     branches:
       only:
         - develop
-        - 'zachw/fix-vite-hoisting-issue'
+        - 'ryanm/fix/improve-binary-cleanup'
 
 # usually we don't build Mac app - it takes a long time
 # but sometimes we want to really confirm we are doing the right thing
@@ -36,7 +36,7 @@ macWorkflowFilters: &darwin-workflow-filters
   when:
     or:
     - equal: [ develop, << pipeline.git.branch >> ]
-    - equal: [ 'zachw/fix-vite-hoisting-issue', << pipeline.git.branch >> ]
+    - equal: [ 'ryanm/fix/improve-binary-cleanup', << pipeline.git.branch >> ]
     - matches:
           pattern: "-release$"
           value: << pipeline.git.branch >>
@@ -45,7 +45,7 @@ linuxArm64WorkflowFilters: &linux-arm64-workflow-filters
   when:
     or:
     - equal: [ develop, << pipeline.git.branch >> ]
-    - equal: [ 'zachw/fix-vite-hoisting-issue', << pipeline.git.branch >> ]
+    - equal: [ 'ryanm/fix/improve-binary-cleanup', << pipeline.git.branch >> ]
     - matches:
           pattern: "-release$"
           value: << pipeline.git.branch >>
@@ -63,7 +63,7 @@ windowsWorkflowFilters: &windows-workflow-filters
   when:
     or:
     - equal: [ develop, << pipeline.git.branch >> ]
-    - equal: [ 'zachw/fix-vite-hoisting-issue', << pipeline.git.branch >> ]
+    - equal: [ 'ryanm/fix/improve-binary-cleanup', << pipeline.git.branch >> ]
     - matches:
           pattern: "-release$"
           value: << pipeline.git.branch >>
@@ -130,7 +130,7 @@ commands:
       - run:
           name: Check current branch to persist artifacts
           command: |
-            if [[ "$CIRCLE_BRANCH" != "develop" && "$CIRCLE_BRANCH" != "zachw/fix-vite-hoisting-issue" ]]; then
+            if [[ "$CIRCLE_BRANCH" != "develop" && "$CIRCLE_BRANCH" != "ryanm/fix/improve-binary-cleanup" ]]; then
               echo "Not uploading artifacts or posting install comment for this branch."
               circleci-agent step halt
             fi
diff --git a/npm/webpack-preprocessor/index.ts b/npm/webpack-preprocessor/index.ts
index a8b98a3e3f5c..3b93af15b35b 100644
--- a/npm/webpack-preprocessor/index.ts
+++ b/npm/webpack-preprocessor/index.ts
@@ -249,7 +249,7 @@ const preprocessor: WebpackPreprocessor = (options: PreprocessorOptions = {}): F
       webpackOptions.module.rules.unshift({
         test: /\.(js|ts|jsx|tsx)$/,
         use: [{
-          loader: path.join(__dirname, 'lib/cross-origin-callback-loader'),
+          loader: require.resolve('@cypress/webpack-preprocessor/dist/lib/cross-origin-callback-loader.js'),
           options: {
             commands: callbackReplacementCommands,
           },
diff --git a/npm/webpack-preprocessor/package.json b/npm/webpack-preprocessor/package.json
index 0d164da248fa..1b1252809ea5 100644
--- a/npm/webpack-preprocessor/package.json
+++ b/npm/webpack-preprocessor/package.json
@@ -20,6 +20,7 @@
     "watch": "rimraf dist && tsc --watch"
   },
   "dependencies": {
+    "@babel/parser": "7.13.0",
     "bluebird": "3.7.1",
     "debug": "^4.3.2",
     "fs-extra": "^10.1.0",
diff --git a/scripts/binary/binary-cleanup.js b/scripts/binary/binary-cleanup.js
index 47ac4c68676c..dc6a70545baf 100644
--- a/scripts/binary/binary-cleanup.js
+++ b/scripts/binary/binary-cleanup.js
@@ -36,22 +36,23 @@ async function removeEmptyDirectories (directory) {
   }
 }
 
-const getDependencyPathsToKeep = async () => {
+const getDependencyPathsToKeep = async (buildAppDir) => {
+  const unixBuildAppDir = buildAppDir.split(path.sep).join(path.posix.sep)
+  const startingEntryPoints = [
+    'packages/server/index.js',
+    'packages/server/hook-require.js',
+    'packages/server/lib/plugins/child/require_async_child.js',
+    'packages/server/lib/plugins/child/register_ts_node.js',
+    'packages/rewriter/lib/threads/worker.js',
+    'node_modules/webpack/lib/webpack.js',
+    'node_modules/webpack-dev-server/lib/Server.js',
+    'node_modules/html-webpack-plugin-4/index.js',
+    'node_modules/html-webpack-plugin-5/index.js',
+    'node_modules/mocha-7.0.1/index.js',
+  ]
+
   let entryPoints = new Set([
-    // This is the entry point for the server bundle. It will not have access to the snapshot yet. It needs to be kept in the binary
-    require.resolve('@packages/server/index.js'),
-    // This is a dynamic import that is used to load the snapshot require logic. It will not have access to the snapshot yet. It needs to be kept in the binary
-    require.resolve('@packages/server/hook-require.js'),
-    // These dependencies are started in a new process or thread and will not have access to the snapshot. They need to be kept in the binary
-    require.resolve('@packages/server/lib/plugins/child/require_async_child.js'),
-    require.resolve('@packages/server/lib/plugins/child/register_ts_node.js'),
-    require.resolve('@packages/rewriter/lib/threads/worker.ts'),
-    // These dependencies use the `require.resolve(<dependency>, { paths: [<path>] })` pattern where <path> is a path within the cypress monorepo. These will not be
-    // pulled in by esbuild but still need to be kept in the binary.
-    require.resolve('webpack'),
-    require.resolve('webpack-dev-server', { paths: [path.join(__dirname, '..', '..', 'npm', 'webpack-dev-server')] }),
-    require.resolve('html-webpack-plugin-4', { paths: [path.join(__dirname, '..', '..', 'npm', 'webpack-dev-server')] }),
-    require.resolve('html-webpack-plugin-5', { paths: [path.join(__dirname, '..', '..', 'npm', 'webpack-dev-server')] }),
+    ...startingEntryPoints.map((entryPoint) => path.join(unixBuildAppDir, entryPoint)),
     // These dependencies are completely dynamic using the pattern `require(`./${name}`)` and will not be pulled in by esbuild but still need to be kept in the binary.
     ...['ibmi',
       'sunos',
@@ -61,7 +62,7 @@ const getDependencyPathsToKeep = async () => {
       'linux',
       'openbsd',
       'sunos',
-      'win32'].map((platform) => require.resolve(`default-gateway/${platform}`)),
+      'win32'].map((platform) => path.join(unixBuildAppDir, `node_modules/default-gateway/${platform}.js`)),
   ])
   let esbuildResult
   let newEntryPointsFound = true
@@ -77,8 +78,10 @@ const getDependencyPathsToKeep = async () => {
       outdir: workingDir,
       platform: 'node',
       metafile: true,
+      absWorkingDir: unixBuildAppDir,
       external: [
-        './packages/server/server-entry',
+        './transpile-ts',
+        './server-entry',
         'fsevents',
         'pnpapi',
         '@swc/core',
@@ -95,9 +98,9 @@ const getDependencyPathsToKeep = async () => {
         let entryPoint
 
         if (warningSubject.startsWith('.')) {
-          entryPoint = path.join(__dirname, '..', '..', path.dirname(warning.location.file), warningSubject)
+          entryPoint = path.join(unixBuildAppDir, path.dirname(warning.location.file), warningSubject)
         } else {
-          entryPoint = require.resolve(warningSubject)
+          entryPoint = require.resolve(warningSubject, { paths: [path.join(unixBuildAppDir, path.dirname(warning.location.file))] })
         }
 
         if (path.extname(entryPoint) !== '' && !entryPoints.has(entryPoint)) {
@@ -114,16 +117,18 @@ const getDependencyPathsToKeep = async () => {
 const cleanup = async (buildAppDir) => {
   // 1. Retrieve all dependencies that still need to be kept in the binary. In theory, we could use the bundles generated here as single files within the binary,
   // but for now, we just track on the dependencies that get pulled in
-  const keptDependencies = [...await getDependencyPathsToKeep(), 'package.json', 'packages/server/server-entry.js']
+  const keptDependencies = [...await getDependencyPathsToKeep(buildAppDir), 'package.json', 'packages/server/server-entry.js']
 
   // 2. Gather the dependencies that could potentially be removed from the binary due to being in the snapshot
   const potentiallyRemovedDependencies = [...snapshotMetadata.healthy, ...snapshotMetadata.deferred, ...snapshotMetadata.norewrite]
 
   // 3. Remove all dependencies that are in the snapshot but not in the list of kept dependencies from the binary
   await Promise.all(potentiallyRemovedDependencies.map(async (dependency) => {
-    // marionette-client requires all of its dependencies in a very non-standard dynamic way. We will keep anything in marionette-client
-    if (!keptDependencies.includes(dependency.slice(2)) && !dependency.includes('marionette-client')) {
-      await fs.remove(path.join(buildAppDir, dependency.replace(/.ts$/, '.js')))
+    const typeScriptlessDependency = dependency.replace(/\.ts$/, '.js')
+
+    // marionette-client and babel/runtime require all of their dependencies in a very non-standard dynamic way. We will keep anything in marionette-client and babel/runtime
+    if (!keptDependencies.includes(typeScriptlessDependency.slice(2)) && !typeScriptlessDependency.includes('marionette-client') && !typeScriptlessDependency.includes('@babel/runtime')) {
+      await fs.remove(path.join(buildAppDir, typeScriptlessDependency))
     }
   }))
 
diff --git a/system-tests/scripts/bootstrap-docker-container.sh b/system-tests/scripts/bootstrap-docker-container.sh
index 19bcda1bf8f9..d74e1fadea0f 100755
--- a/system-tests/scripts/bootstrap-docker-container.sh
+++ b/system-tests/scripts/bootstrap-docker-container.sh
@@ -39,7 +39,7 @@ export npm_config_package_lock=false
 mkdir $npm_config_cache
 chown -R 1000:1000 $npm_config_cache
 
-npx npm@latest install --unsafe-perm --allow-root --force file:$CLI_PATH
+npx npm@8 install --unsafe-perm --allow-root --force file:$CLI_PATH
 
 PATH=$PATH:./node_modules/.bin
 
diff --git a/tooling/v8-snapshot/cache/prod-darwin/snapshot-meta.cache.json b/tooling/v8-snapshot/cache/prod-darwin/snapshot-meta.cache.json
index 2dbe1a95ef92..94474b178204 100644
--- a/tooling/v8-snapshot/cache/prod-darwin/snapshot-meta.cache.json
+++ b/tooling/v8-snapshot/cache/prod-darwin/snapshot-meta.cache.json
@@ -49,6 +49,8 @@
     "./packages/server/lib/modes/record.js",
     "./packages/server/lib/modes/run.ts",
     "./packages/server/lib/open_project.ts",
+    "./packages/server/lib/project-base.ts",
+    "./packages/server/lib/socket-ct.ts",
     "./packages/server/lib/util/suppress_warnings.js",
     "./packages/server/node_modules/@benmalka/foxdriver/node_modules/graceful-fs/polyfills.js",
     "./packages/server/node_modules/glob/node_modules/minimatch/minimatch.js",
@@ -844,7 +846,6 @@
     "./packages/server/lib/plugins/dev-server.js",
     "./packages/server/lib/plugins/preprocessor.js",
     "./packages/server/lib/plugins/run_events.js",
-    "./packages/server/lib/project-base.ts",
     "./packages/server/lib/project_utils.ts",
     "./packages/server/lib/remote_states.ts",
     "./packages/server/lib/reporter.js",
@@ -857,7 +858,6 @@
     "./packages/server/lib/server-ct.ts",
     "./packages/server/lib/server-e2e.ts",
     "./packages/server/lib/socket-base.ts",
-    "./packages/server/lib/socket-ct.ts",
     "./packages/server/lib/socket-e2e.ts",
     "./packages/server/lib/unhandled_exceptions.ts",
     "./packages/server/lib/util/app_data.js",
@@ -3929,5 +3929,5 @@
     "./tooling/v8-snapshot/cache/prod-darwin/snapshot-entry.js"
   ],
   "deferredHashFile": "yarn.lock",
-  "deferredHash": "95205f49259fe2d246d45ef15d1499f6e3d1d235d6db892124bbd5423f1ba872"
+  "deferredHash": "8b71698b89d3804ed712295c20a140cfcd674fa5c3ad9569530282dd6c3e9906"
 }
\ No newline at end of file
diff --git a/tooling/v8-snapshot/cache/prod-linux/snapshot-meta.cache.json b/tooling/v8-snapshot/cache/prod-linux/snapshot-meta.cache.json
index 61fc0d6d6cd6..e5959db684fd 100644
--- a/tooling/v8-snapshot/cache/prod-linux/snapshot-meta.cache.json
+++ b/tooling/v8-snapshot/cache/prod-linux/snapshot-meta.cache.json
@@ -49,6 +49,8 @@
     "./packages/server/lib/modes/record.js",
     "./packages/server/lib/modes/run.ts",
     "./packages/server/lib/open_project.ts",
+    "./packages/server/lib/project-base.ts",
+    "./packages/server/lib/socket-ct.ts",
     "./packages/server/lib/util/suppress_warnings.js",
     "./packages/server/node_modules/@benmalka/foxdriver/node_modules/graceful-fs/polyfills.js",
     "./packages/server/node_modules/glob/node_modules/minimatch/minimatch.js",
@@ -843,7 +845,6 @@
     "./packages/server/lib/plugins/dev-server.js",
     "./packages/server/lib/plugins/preprocessor.js",
     "./packages/server/lib/plugins/run_events.js",
-    "./packages/server/lib/project-base.ts",
     "./packages/server/lib/project_utils.ts",
     "./packages/server/lib/remote_states.ts",
     "./packages/server/lib/reporter.js",
@@ -856,7 +857,6 @@
     "./packages/server/lib/server-ct.ts",
     "./packages/server/lib/server-e2e.ts",
     "./packages/server/lib/socket-base.ts",
-    "./packages/server/lib/socket-ct.ts",
     "./packages/server/lib/socket-e2e.ts",
     "./packages/server/lib/unhandled_exceptions.ts",
     "./packages/server/lib/util/app_data.js",
diff --git a/tooling/v8-snapshot/cache/prod-win32/snapshot-meta.cache.json b/tooling/v8-snapshot/cache/prod-win32/snapshot-meta.cache.json
index c0c3943ff8e6..86d740dacfe6 100644
--- a/tooling/v8-snapshot/cache/prod-win32/snapshot-meta.cache.json
+++ b/tooling/v8-snapshot/cache/prod-win32/snapshot-meta.cache.json
@@ -49,6 +49,8 @@
     "./packages/server/lib/modes/record.js",
     "./packages/server/lib/modes/run.ts",
     "./packages/server/lib/open_project.ts",
+    "./packages/server/lib/project-base.ts",
+    "./packages/server/lib/socket-ct.ts",
     "./packages/server/lib/util/suppress_warnings.js",
     "./packages/server/node_modules/@benmalka/foxdriver/node_modules/graceful-fs/polyfills.js",
     "./packages/server/node_modules/glob/node_modules/minimatch/minimatch.js",
@@ -846,7 +848,6 @@
     "./packages/server/lib/plugins/dev-server.js",
     "./packages/server/lib/plugins/preprocessor.js",
     "./packages/server/lib/plugins/run_events.js",
-    "./packages/server/lib/project-base.ts",
     "./packages/server/lib/project_utils.ts",
     "./packages/server/lib/remote_states.ts",
     "./packages/server/lib/reporter.js",
@@ -859,7 +860,6 @@
     "./packages/server/lib/server-ct.ts",
     "./packages/server/lib/server-e2e.ts",
     "./packages/server/lib/socket-base.ts",
-    "./packages/server/lib/socket-ct.ts",
     "./packages/server/lib/socket-e2e.ts",
     "./packages/server/lib/unhandled_exceptions.ts",
     "./packages/server/lib/util/app_data.js",
diff --git a/tooling/v8-snapshot/src/setup/force-no-rewrite.ts b/tooling/v8-snapshot/src/setup/force-no-rewrite.ts
index 1449b0475684..077365a6d8de 100644
--- a/tooling/v8-snapshot/src/setup/force-no-rewrite.ts
+++ b/tooling/v8-snapshot/src/setup/force-no-rewrite.ts
@@ -56,4 +56,6 @@ export default [
   'packages/server/node_modules/glob/node_modules/minimatch/minimatch.js',
   'node_modules/js-yaml/lib/js-yaml/type/js/function.js',
   'packages/server/lib/open_project.ts',
+  'packages/server/lib/project-base.ts',
+  'packages/server/lib/socket-ct.ts',
 ]