diff --git a/packages/client/tests/functional/issues/16196-upsert-nested-select/_matrix.ts b/packages/client/tests/functional/issues/16196-upsert-nested-select/_matrix.ts
new file mode 100644
index 000000000000..58ad17761d3d
--- /dev/null
+++ b/packages/client/tests/functional/issues/16196-upsert-nested-select/_matrix.ts
@@ -0,0 +1,15 @@
+import { defineMatrix } from '../../_utils/defineMatrix'
+
+export default defineMatrix(() => [
+  [
+    {
+      provider: 'sqlite',
+    },
+    {
+      provider: 'postgresql',
+    },
+    {
+      provider: 'cockroachdb',
+    },
+  ],
+])
diff --git a/packages/client/tests/functional/issues/16196-upsert-nested-select/prisma/_schema.ts b/packages/client/tests/functional/issues/16196-upsert-nested-select/prisma/_schema.ts
new file mode 100644
index 000000000000..462e7e5cd59e
--- /dev/null
+++ b/packages/client/tests/functional/issues/16196-upsert-nested-select/prisma/_schema.ts
@@ -0,0 +1,36 @@
+import { idForProvider } from '../../../_utils/idForProvider'
+import testMatrix from '../_matrix'
+
+export default testMatrix.setupSchema(({ provider }) => {
+  return /* Prisma */ `
+  generator client {
+    provider = "prisma-client-js"
+  }
+  
+  datasource db {
+    provider = "${provider}"
+    url      = env("DATABASE_URI_${provider}")
+  }
+  
+  model User {
+    id ${idForProvider(provider)}
+    email String @unique
+    posts Post[]
+    profile Profile?
+  }
+
+  model Post {
+    id ${idForProvider(provider)}
+    title String
+    user User @relation(fields: [userId], references: [id])
+    userId String
+  }
+
+  model Profile {
+    id ${idForProvider(provider)}
+    name String
+    user User @relation(fields: [userId], references: [id])
+    userId String @unique
+  }
+  `
+})
diff --git a/packages/client/tests/functional/issues/16196-upsert-nested-select/tests.ts b/packages/client/tests/functional/issues/16196-upsert-nested-select/tests.ts
new file mode 100644
index 000000000000..5f08cc6bec32
--- /dev/null
+++ b/packages/client/tests/functional/issues/16196-upsert-nested-select/tests.ts
@@ -0,0 +1,131 @@
+import { randomBytes } from 'crypto'
+
+import testMatrix from './_matrix'
+// @ts-ignore
+import type { PrismaClient } from './node_modules/@prisma/client'
+
+declare let prisma: PrismaClient
+
+const id = randomBytes(12).toString('hex')
+testMatrix.setupTestSuite(
+  (suiteConfig, suiteMeta) => {
+    beforeAll(async () => {
+      await prisma.user.create({
+        data: {
+          id: id,
+          email: 'john@doe.io',
+          posts: {
+            create: [{ title: 'A' }, { title: 'B' }, { title: 'C' }],
+          },
+        },
+      })
+    })
+
+    test('upsert (update) with nested select many relation', async () => {
+      const data = await prisma.user.upsert({
+        where: { id },
+        create: {
+          email: 'john@doe.io',
+        },
+        update: {
+          email: 'johnny@doe.io',
+        },
+        select: {
+          posts: {
+            select: {
+              user: {
+                select: {
+                  email: true,
+                },
+              },
+            },
+          },
+        },
+      })
+
+      expect(data).toMatchInlineSnapshot(`
+        Object {
+          posts: Array [
+            Object {
+              user: Object {
+                email: johnny@doe.io,
+              },
+            },
+            Object {
+              user: Object {
+                email: johnny@doe.io,
+              },
+            },
+            Object {
+              user: Object {
+                email: johnny@doe.io,
+              },
+            },
+          ],
+        }
+      `)
+    })
+
+    test('upsert (update) with nested select one relation', async () => {
+      const data = await prisma.user.upsert({
+        where: { id },
+        create: {
+          email: 'john@doe.io',
+        },
+        update: {
+          email: 'johnny@doe.io',
+        },
+        select: {
+          profile: {
+            select: {
+              user: {
+                select: {
+                  email: true,
+                },
+              },
+            },
+          },
+        },
+      })
+
+      expect(data).toMatchInlineSnapshot(`
+        Object {
+          profile: null,
+        }
+      `)
+    })
+
+    test('upsert (create) with nested select one relation', async () => {
+      const data = await prisma.user.upsert({
+        where: { id: randomBytes(12).toString('hex') },
+        create: {
+          email: 'jane@joe.io',
+        },
+        update: {
+          email: 'janette@doe.io',
+        },
+        select: {
+          email: true,
+          profile: {
+            select: {
+              id: true,
+            },
+          },
+        },
+      })
+
+      expect(data).toMatchInlineSnapshot(`
+        Object {
+          email: jane@joe.io,
+          profile: null,
+        }
+      `)
+    })
+  },
+  {
+    optOut: {
+      from: ['mysql', 'mongodb', 'sqlserver'],
+      reason: "We don't support native upserts for these",
+    },
+  },
+)