diff --git a/frontend/src/component/playground/Playground/PlaygroundForm/PlaygroundCodeFieldset/PlaygroundCodeFieldset.tsx b/frontend/src/component/playground/Playground/PlaygroundForm/PlaygroundCodeFieldset/PlaygroundCodeFieldset.tsx
index 78fd33c8a9..a0f93cc0c4 100644
--- a/frontend/src/component/playground/Playground/PlaygroundForm/PlaygroundCodeFieldset/PlaygroundCodeFieldset.tsx
+++ b/frontend/src/component/playground/Playground/PlaygroundForm/PlaygroundCodeFieldset/PlaygroundCodeFieldset.tsx
@@ -27,7 +27,10 @@ import { formatUnknownError } from 'utils/formatUnknownError';
 import useToast from 'hooks/useToast';
 import { PlaygroundEditor } from './PlaygroundEditor/PlaygroundEditor';
 import { parseDateValue, parseValidDate } from 'component/common/util';
-import { isStringOrStringArray } from '../../playground.utils';
+import {
+    isStringOrStringArray,
+    normalizeCustomContextProperties,
+} from '../../playground.utils';
 interface IPlaygroundCodeFieldsetProps {
     context: string | undefined;
     setContext: Dispatch<SetStateAction<string | undefined>>;
@@ -58,7 +61,10 @@ export const PlaygroundCodeFieldset: VFC<IPlaygroundCodeFieldsetProps> = ({
                 try {
                     const contextValue = JSON.parse(input);
 
-                    setFieldExist(contextValue[contextField] !== undefined);
+                    setFieldExist(
+                        contextValue[contextField] !== undefined ||
+                            contextValue?.properties[contextField] !== undefined
+                    );
                 } catch (error: unknown) {
                     return setError(formatUnknownError(error));
                 }
@@ -75,12 +81,13 @@ export const PlaygroundCodeFieldset: VFC<IPlaygroundCodeFieldsetProps> = ({
     const onAddField = () => {
         try {
             const currentValue = JSON.parse(context || '{}');
+
             setContext(
                 JSON.stringify(
-                    {
+                    normalizeCustomContextProperties({
                         ...currentValue,
                         [contextField]: contextValue,
-                    },
+                    }),
                     null,
                     2
                 )
diff --git a/frontend/src/component/playground/Playground/playground.utils.test.ts b/frontend/src/component/playground/Playground/playground.utils.test.ts
new file mode 100644
index 0000000000..16e53201e7
--- /dev/null
+++ b/frontend/src/component/playground/Playground/playground.utils.test.ts
@@ -0,0 +1,78 @@
+import {
+    normalizeCustomContextProperties,
+    NormalizedContextProperties,
+} from './playground.utils';
+
+test('should keep standard properties in their place', () => {
+    const input: NormalizedContextProperties = {
+        appName: 'testApp',
+        environment: 'testEnv',
+        userId: 'testUser',
+        sessionId: 'testSession',
+        remoteAddress: '127.0.0.1',
+        currentTime: 'now',
+    };
+    const output = normalizeCustomContextProperties(input);
+    expect(output).toEqual(input);
+});
+
+test('should move non-standard properties to nested properties field', () => {
+    const input = {
+        appName: 'testApp',
+        customProp: 'customValue',
+        anotherCustom: 'anotherValue',
+    };
+    const output = normalizeCustomContextProperties(input);
+    expect(output).toEqual({
+        appName: 'testApp',
+        properties: {
+            customProp: 'customValue',
+            anotherCustom: 'anotherValue',
+        },
+    });
+});
+
+test('should not have properties field if there are no non-standard properties', () => {
+    const input = {
+        appName: 'testApp',
+    };
+    const output = normalizeCustomContextProperties(input);
+    expect(output).toEqual(input);
+    expect(output.properties).toBeUndefined();
+});
+
+test('should combine existing properties field with non-standard properties', () => {
+    const input = {
+        appName: 'testApp',
+        properties: {
+            existingProp: 'existingValue',
+        },
+        customProp: 'customValue',
+    };
+    const output = normalizeCustomContextProperties(input);
+    expect(output).toEqual({
+        appName: 'testApp',
+        properties: {
+            existingProp: 'existingValue',
+            customProp: 'customValue',
+        },
+    });
+});
+
+test('should add multiple standard properties without breaking custom properties', () => {
+    const input = {
+        appName: 'testApp',
+        properties: {
+            existingProp: 'existingValue',
+        },
+        currentTime: 'value',
+    };
+    const output = normalizeCustomContextProperties(input);
+    expect(output).toEqual({
+        appName: 'testApp',
+        currentTime: 'value',
+        properties: {
+            existingProp: 'existingValue',
+        },
+    });
+});
diff --git a/frontend/src/component/playground/Playground/playground.utils.ts b/frontend/src/component/playground/Playground/playground.utils.ts
index f3ae68cb97..9b68b94cb2 100644
--- a/frontend/src/component/playground/Playground/playground.utils.ts
+++ b/frontend/src/component/playground/Playground/playground.utils.ts
@@ -73,3 +73,55 @@ export const isStringOrStringArray = (
 
     return false;
 };
+
+type InputContextProperties = {
+    appName?: string;
+    environment?: string;
+    userId?: string;
+    sessionId?: string;
+    remoteAddress?: string;
+    currentTime?: string;
+    properties?: { [key: string]: any };
+    [key: string]: any;
+};
+
+export type NormalizedContextProperties = Omit<
+    InputContextProperties,
+    'properties'
+> & {
+    properties?: { [key: string]: any };
+};
+
+export const normalizeCustomContextProperties = (
+    input: InputContextProperties
+): NormalizedContextProperties => {
+    const standardProps = new Set([
+        'appName',
+        'environment',
+        'userId',
+        'sessionId',
+        'remoteAddress',
+        'currentTime',
+        'properties',
+    ]);
+
+    const output: InputContextProperties = { ...input };
+    let hasCustomProperties = false;
+
+    for (const key in input) {
+        if (!standardProps.has(key)) {
+            if (!output.properties) {
+                output.properties = {};
+            }
+            output.properties[key] = input[key];
+            delete output[key];
+            hasCustomProperties = true;
+        }
+    }
+
+    if (!hasCustomProperties && !input.properties) {
+        delete output.properties;
+    }
+
+    return output;
+};
diff --git a/src/lib/features/playground/generateObjectCombinations.test.ts b/src/lib/features/playground/generateObjectCombinations.test.ts
index e21356a594..e77dbfc1fc 100644
--- a/src/lib/features/playground/generateObjectCombinations.test.ts
+++ b/src/lib/features/playground/generateObjectCombinations.test.ts
@@ -37,3 +37,28 @@ test('should generate all combinations correctly when only one combination', ()
 
     expect(actualCombinations).toEqual(expectedCombinations);
 });
+
+test('should generate combinations with nested properties', () => {
+    const obj = {
+        sessionId: '1,2',
+        nonString: 2,
+        properties: {
+            nonString: 1,
+            channels: 'internet',
+            appName: 'a,b,c',
+        },
+    };
+
+    const expectedCombinations = [
+        { sessionId: '1', appName: 'a', channels: 'internet', nonString: 1 },
+        { sessionId: '1', appName: 'b', channels: 'internet', nonString: 1 },
+        { sessionId: '1', appName: 'c', channels: 'internet', nonString: 1 },
+        { sessionId: '2', appName: 'a', channels: 'internet', nonString: 1 },
+        { sessionId: '2', appName: 'b', channels: 'internet', nonString: 1 },
+        { sessionId: '2', appName: 'c', channels: 'internet', nonString: 1 },
+    ];
+
+    const actualCombinations = generateObjectCombinations(obj);
+
+    expect(actualCombinations).toEqual(expectedCombinations);
+});
diff --git a/src/lib/features/playground/generateObjectCombinations.ts b/src/lib/features/playground/generateObjectCombinations.ts
index 78c1f073df..8f40ed270d 100644
--- a/src/lib/features/playground/generateObjectCombinations.ts
+++ b/src/lib/features/playground/generateObjectCombinations.ts
@@ -1,14 +1,19 @@
-type Dict<T> = { [K in keyof T]: string[] };
+type Dict<T> = { [K in keyof T]: (string | number)[] };
 
 export const splitByComma = <T extends Record<string, unknown>>(
     obj: T,
-): Dict<T> =>
-    Object.fromEntries(
-        Object.entries(obj).map(([key, value]) => [
-            key,
-            typeof value === 'string' ? value.split(',') : [value],
-        ]),
-    ) as Dict<T>;
+): Dict<T> => {
+    return Object.entries(obj).reduce((acc, [key, value]) => {
+        if (key === 'properties' && typeof value === 'object') {
+            const nested = splitByComma(value as any);
+            return { ...acc, ...nested };
+        } else if (typeof value === 'string') {
+            return { ...acc, [key]: value.split(',') };
+        } else {
+            return { ...acc, [key]: [value] };
+        }
+    }, {} as Dict<T>);
+};
 
 export const generateCombinations = <T extends Record<string, unknown>>(
     obj: Dict<T>,