diff --git a/package-lock.json b/package-lock.json
index 19218301708..8ac520b30fc 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -22882,7 +22882,7 @@
       }
     },
     "packages/insomnia": {
-      "version": "10.2.0",
+      "version": "10.2.1-beta.1",
       "license": "Apache-2.0",
       "dependencies": {
         "@apideck/better-ajv-errors": "^0.3.6",
@@ -23035,7 +23035,7 @@
       }
     },
     "packages/insomnia-inso": {
-      "version": "10.2.0",
+      "version": "10.2.1-beta.1",
       "license": "Apache-2.0",
       "dependencies": {
         "@seald-io/nedb": "^4.0.4",
@@ -23068,7 +23068,7 @@
       "license": "MIT"
     },
     "packages/insomnia-sdk": {
-      "version": "10.2.0",
+      "version": "10.2.1-beta.1",
       "license": "Apache-2.0",
       "dependencies": {
         "@types/deep-equal": "^1.0.4",
@@ -23120,7 +23120,7 @@
       }
     },
     "packages/insomnia-smoke-test": {
-      "version": "10.2.0",
+      "version": "10.2.1-beta.1",
       "license": "Apache-2.0",
       "devDependencies": {
         "@grpc/grpc-js": "^1.12.00",
@@ -23148,7 +23148,7 @@
       }
     },
     "packages/insomnia-testing": {
-      "version": "10.2.0",
+      "version": "10.2.1-beta.1",
       "license": "Apache-2.0"
     }
   }
diff --git a/packages/insomnia-inso/package.json b/packages/insomnia-inso/package.json
index ff52a7a06a6..18d0c3cba99 100644
--- a/packages/insomnia-inso/package.json
+++ b/packages/insomnia-inso/package.json
@@ -1,7 +1,7 @@
 {
   "private": true,
   "name": "insomnia-inso",
-  "version": "10.2.0",
+  "version": "10.2.1-beta.1",
   "homepage": "https://insomnia.rest",
   "description": "A CLI for Insomnia - The Collaborative API Design Tool",
   "author": "Kong <office@konghq.com>",
diff --git a/packages/insomnia-sdk/package.json b/packages/insomnia-sdk/package.json
index f571b120128..25dc8f4d83a 100644
--- a/packages/insomnia-sdk/package.json
+++ b/packages/insomnia-sdk/package.json
@@ -1,7 +1,7 @@
 {
   "private": true,
   "name": "insomnia-sdk",
-  "version": "10.2.0",
+  "version": "10.2.1-beta.1",
   "description": "",
   "main": "src/objects/index.ts",
   "types": "src/objects/index.ts",
diff --git a/packages/insomnia-smoke-test/fixtures/simple.yaml b/packages/insomnia-smoke-test/fixtures/simple.yaml
index 068f71ae297..4f6fbb2367b 100644
--- a/packages/insomnia-smoke-test/fixtures/simple.yaml
+++ b/packages/insomnia-smoke-test/fixtures/simple.yaml
@@ -24,6 +24,8 @@ resources:
     settingRebuildPath: true
     settingFollowRedirects: global
     _type: request
+    preRequestScript: |-
+      console.log('executing pre-request script');
   - _id: fld_01de564274824ecaad272330339ea6b2
     parentId: wrk_0702a57d75d44255a8cecd2c5fa87809
     modified: 1668533312225
@@ -101,6 +103,8 @@ resources:
     settingRebuildPath: true
     settingFollowRedirects: global
     _type: request
+    preRequestScript: |-
+      console.log('executing pre-request script');
   - _id: req_579daeabc7534a52b242bdaaaf6ca4dc
     parentId: wrk_0702a57d75d44255a8cecd2c5fa87809
     modified: 1666867670885
@@ -122,6 +126,8 @@ resources:
     settingRebuildPath: true
     settingFollowRedirects: global
     _type: request
+    preRequestScript: |-
+      console.log('executing pre-request script');
   - _id: env_42a94488fcd6106a75fb3ededd6bb4fbd267aa95
     parentId: wrk_0702a57d75d44255a8cecd2c5fa87809
     modified: 1666867924188
diff --git a/packages/insomnia-smoke-test/package.json b/packages/insomnia-smoke-test/package.json
index 759129355b1..387d6435b44 100644
--- a/packages/insomnia-smoke-test/package.json
+++ b/packages/insomnia-smoke-test/package.json
@@ -11,7 +11,7 @@
   "bugs": {
     "url": "https://github.com/kong/insomnia/issues"
   },
-  "version": "10.2.0",
+  "version": "10.2.1-beta.1",
   "scripts": {
     "test:dev": "xvfb-maybe cross-env BUNDLE=dev playwright test",
     "test:build": "xvfb-maybe cross-env BUNDLE=build playwright test",
diff --git a/packages/insomnia-testing/package.json b/packages/insomnia-testing/package.json
index 18ce16c516c..87e183ea80e 100644
--- a/packages/insomnia-testing/package.json
+++ b/packages/insomnia-testing/package.json
@@ -2,7 +2,7 @@
   "private": true,
   "name": "insomnia-testing",
   "license": "Apache-2.0",
-  "version": "10.2.0",
+  "version": "10.2.1-beta.1",
   "author": "Kong <office@konghq.com>",
   "repository": {
     "type": "git",
diff --git a/packages/insomnia/package.json b/packages/insomnia/package.json
index c7dd05a910b..287594ea02b 100644
--- a/packages/insomnia/package.json
+++ b/packages/insomnia/package.json
@@ -1,6 +1,6 @@
 {
   "name": "insomnia",
-  "version": "10.2.0",
+  "version": "10.2.1-beta.1",
   "productName": "Insomnia",
   "private": true,
   "description": "The Collaborative API Design Tool",
diff --git a/packages/insomnia/src/common/send-request.ts b/packages/insomnia/src/common/send-request.ts
index 9f2e7329d3f..d6ae1755f54 100644
--- a/packages/insomnia/src/common/send-request.ts
+++ b/packages/insomnia/src/common/send-request.ts
@@ -1,3 +1,4 @@
+import fs from 'fs/promises';
 import path from 'path';
 
 import { type BaseModel, types as modelTypes } from '../models';
@@ -122,6 +123,7 @@ export async function getSendRequestCallbackMemDb(environmentId: string, memDB:
   return async function sendRequest(requestId: string, iteration?: number) {
     const requestData = await fetchInsoRequestData(requestId, environmentId);
     const getCurrentRowOfIterationData = wrapAroundIterationOverIterationData(iterationData, iteration);
+    await fs.mkdir(path.dirname(requestData.timelinePath), { recursive: true });
 
     const mutatedContext = await tryToExecutePreRequestScript(requestData, transientVariables, getCurrentRowOfIterationData, iteration, iterationCount);
     if (mutatedContext === null) {