diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/constants.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/constants.js
new file mode 100644
index 00000000000..8751dd4c374
--- /dev/null
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/constants.js
@@ -0,0 +1,6 @@
+/**
+ * @prettier
+ */
+export const SCALAR_TYPES = ["integer", "number", "string", "boolean", "null"]
+
+export const ALL_TYPES = ["array", "object", ...SCALAR_TYPES]
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/fold-type.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/fold-type.js
new file mode 100644
index 00000000000..c8a19f75781
--- /dev/null
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/fold-type.js
@@ -0,0 +1,24 @@
+/**
+ * @prettier
+ */
+import { ALL_TYPES } from "./constants"
+
+const foldType = (type) => {
+  if (Array.isArray(type)) {
+    if (type.includes("array")) {
+      return "array"
+    } else if (type.includes("object")) {
+      return "object"
+    } else if (ALL_TYPES.includes(type.at(0))) {
+      return type.at(0)
+    }
+  }
+
+  if (typeof type === "string" && ALL_TYPES.includes(type)) {
+    return type
+  }
+
+  return null
+}
+
+export default foldType
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/predicates.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/predicates.js
new file mode 100644
index 00000000000..ae0bf044fd0
--- /dev/null
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/predicates.js
@@ -0,0 +1,24 @@
+/**
+ * @prettier
+ */
+import isPlainObject from "lodash/isPlainObject"
+
+export const isURI = (uri) => {
+  try {
+    return new URL(uri) && true
+  } catch {
+    return false
+  }
+}
+
+export const isBooleanJSONSchema = (schema) => {
+  return typeof schema === "boolean"
+}
+
+export const isJSONSchemaObject = (schema) => {
+  return isPlainObject(schema)
+}
+
+export const isJSONSchema = (schema) => {
+  return isBooleanJSONSchema(schema) || isJSONSchemaObject(schema)
+}
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/utils.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/utils.js
index 6d6f5a18a3c..df40a0bac32 100644
--- a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/utils.js
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/core/utils.js
@@ -1,10 +1,23 @@
 /**
  * @prettier
  */
-export const isURI = (uri) => {
-  try {
-    return new URL(uri) && true
-  } catch {
-    return false
+import { isBooleanJSONSchema, isJSONSchemaObject } from "./predicates"
+
+export const fromJSONBooleanSchema = (schema) => {
+  if (schema === false) {
+    return { not: {} }
   }
+
+  return {}
+}
+
+export const typeCast = (schema) => {
+  if (isBooleanJSONSchema(schema)) {
+    return fromJSONBooleanSchema(schema)
+  }
+  if (!isJSONSchemaObject(schema)) {
+    return {}
+  }
+
+  return schema
 }
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/main.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/main.js
index e0775be5bfc..555aac47b2a 100644
--- a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/main.js
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/main.js
@@ -4,22 +4,12 @@
 import XML from "xml"
 import isEmpty from "lodash/isEmpty"
 
-import { objectify, isFunc, normalizeArray, deeplyStripKey } from "core/utils"
+import { objectify, normalizeArray, deeplyStripKey } from "core/utils"
 import memoizeN from "../../../../../helpers/memoizeN"
 import typeMap from "./types/index"
-import { isURI } from "./core/utils"
-
-const primitive = (schema) => {
-  schema = objectify(schema)
-  const { type: typeList } = schema
-  const type = Array.isArray(typeList) ? typeList.at(0) : typeList
-
-  if (Object.hasOwn(typeMap, type)) {
-    return typeMap[type](schema)
-  }
-
-  return `Unknown Type: ${type}`
-}
+import { isURI } from "./core/predicates"
+import foldType from "./core/fold-type"
+import { typeCast } from "./core/utils"
 
 /**
  * Do a couple of quick sanity tests to ensure the value
@@ -140,7 +130,9 @@ export const sampleFromSchemaGeneric = (
   exampleOverride = undefined,
   respectXML = false
 ) => {
-  if (schema && isFunc(schema.toJS)) schema = schema.toJS()
+  if (typeof schema?.toJS === "function") schema = schema.toJS()
+  schema = typeCast(schema)
+
   let usePlainValue =
     exampleOverride !== undefined ||
     (schema && schema.example !== undefined) ||
@@ -151,7 +143,7 @@ export const sampleFromSchemaGeneric = (
   const hasAnyOf =
     !usePlainValue && schema && schema.anyOf && schema.anyOf.length > 0
   if (!usePlainValue && (hasOneOf || hasAnyOf)) {
-    const schemaToAdd = objectify(hasOneOf ? schema.oneOf[0] : schema.anyOf[0])
+    const schemaToAdd = typeCast(hasOneOf ? schema.oneOf[0] : schema.anyOf[0])
     liftSampleHelper(schemaToAdd, schema, config)
     if (!schema.xml && schemaToAdd.xml) {
       schema.xml = schemaToAdd.xml
@@ -211,6 +203,7 @@ export const sampleFromSchemaGeneric = (
     items,
     contains,
   } = schema || {}
+  type = foldType(type)
   let { includeReadOnly, includeWriteOnly } = config
   xml = xml || {}
   let { name, prefix, namespace } = xml
@@ -339,9 +332,9 @@ export const sampleFromSchemaGeneric = (
           } else if (enumAttrVal !== undefined) {
             _attr[props[propName].xml.name || propName] = enumAttrVal
           } else {
-            _attr[props[propName].xml.name || propName] = primitive(
-              props[propName]
-            )
+            const propSchema = typeCast(props[propName])
+            const attrName = props[propName].xml.name || propName
+            _attr[attrName] = typeMap[propSchema.type](propSchema)
           }
 
           return
@@ -468,7 +461,7 @@ export const sampleFromSchemaGeneric = (
         ]
       }
 
-      itemSamples = typeMap.array(schema, itemSamples)
+      itemSamples = typeMap.array(schema, { sample: itemSamples })
       if (xml.wrapped) {
         res[displayName] = itemSamples
         if (!isEmpty(_attr)) {
@@ -606,7 +599,7 @@ export const sampleFromSchemaGeneric = (
       }
     }
 
-    sampleArray = typeMap.array(schema, sampleArray)
+    sampleArray = typeMap.array(schema, { sample: sampleArray })
     if (respectXML && xml.wrapped) {
       res[displayName] = sampleArray
       if (!isEmpty(_attr)) {
@@ -650,7 +643,7 @@ export const sampleFromSchemaGeneric = (
       }
       propertyAddedCounter++
     } else if (additionalProperties) {
-      const additionalProps = objectify(additionalProperties)
+      const additionalProps = typeCast(additionalProperties)
       const additionalPropSample = sampleFromSchemaGeneric(
         additionalProps,
         config,
@@ -699,7 +692,15 @@ export const sampleFromSchemaGeneric = (
     value = normalizeArray(schema.enum)[0]
   } else if (schema) {
     // display schema default
-    value = primitive(schema)
+    const contentSample = Object.hasOwn(schema, "contentSchema")
+      ? sampleFromSchemaGeneric(
+          typeCast(schema.contentSchema),
+          config,
+          undefined,
+          respectXML
+        )
+      : undefined
+    value = typeMap[type](schema, { sample: contentSample })
   } else {
     return
   }
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/array.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/array.js
index abef5fc8ca4..babaf619d55 100644
--- a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/array.js
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/array.js
@@ -45,8 +45,8 @@ export const applyArrayConstraints = (array, constraints = {}) => {
   return constrainedArray
 }
 
-const arrayType = (schema, sampleArray) => {
-  return applyArrayConstraints(sampleArray, schema)
+const arrayType = (schema, { sample }) => {
+  return applyArrayConstraints(sample, schema)
 }
 
 export default arrayType
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/index.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/index.js
index dbd05c34768..6d7aeda8cbb 100644
--- a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/index.js
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/index.js
@@ -19,4 +19,12 @@ const typeMap = {
   null: nullType,
 }
 
-export default typeMap
+export default new Proxy(typeMap, {
+  get(target, prop) {
+    if (Object.hasOwn(target, prop)) {
+      return target[prop]
+    }
+
+    return () => `Unknown Type: ${prop}`
+  },
+})
diff --git a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/string.js b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/string.js
index 0db8dd999d1..1ba14250137 100644
--- a/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/string.js
+++ b/src/core/plugins/json-schema-2020-12/samples-extensions/fn/types/string.js
@@ -4,6 +4,7 @@
 import identity from "lodash/identity"
 
 import { string as randomString, randexp } from "../core/random"
+import { isJSONSchema } from "../core/predicates"
 import emailGenerator from "../generators/email"
 import idnEmailGenerator from "../generators/idn-email"
 import hostnameGenerator from "../generators/hostname"
@@ -118,8 +119,9 @@ const applyStringConstraints = (string, constraints = {}) => {
 
   return constrainedString
 }
-const stringType = (schema) => {
-  const { pattern, format, contentEncoding, contentMediaType } = schema
+const stringType = (schema, { sample } = {}) => {
+  const { contentEncoding, contentMediaType, contentSchema } = schema
+  const { pattern, format } = schema
   const encode = encoderAPI(contentEncoding) || identity
   let generatedString
 
@@ -127,7 +129,17 @@ const stringType = (schema) => {
     generatedString = randexp(pattern)
   } else if (typeof format === "string") {
     generatedString = generateFormat(schema)
-  } else if (typeof contentMediaType === "string") {
+  } else if (
+    isJSONSchema(contentSchema) &&
+    typeof contentMediaType !== "undefined" &&
+    typeof sample !== "undefined"
+  ) {
+    if (Array.isArray(sample) || typeof sample === "object") {
+      generatedString = JSON.stringify(sample)
+    } else {
+      generatedString = String(sample)
+    }
+  } else if (typeof contentMediaType !== "undefined") {
     const mediaTypeGenerator = mediaTypeAPI(contentMediaType)
     if (typeof mediaTypeGenerator === "function") {
       generatedString = mediaTypeGenerator(schema)
diff --git a/test/unit/core/plugins/json-schema-2020-12/samples-extensions/fn.js b/test/unit/core/plugins/json-schema-2020-12/samples-extensions/fn.js
index 9e1309b95c2..e84fcfe730f 100644
--- a/test/unit/core/plugins/json-schema-2020-12/samples-extensions/fn.js
+++ b/test/unit/core/plugins/json-schema-2020-12/samples-extensions/fn.js
@@ -2,7 +2,6 @@
  * @prettier
  *
  */
-import { Buffer } from "node:buffer"
 import { fromJS } from "immutable"
 import {
   createXMLExample,
@@ -291,6 +290,58 @@ describe("sampleFromSchema", () => {
     expect(sampleFromSchema(definition)).toMatch(base64Regex)
   })
 
+  it("should handle contentSchema defined as type=object", function () {
+    const definition = fromJS({
+      type: "string",
+      contentMediaType: "application/json",
+      contentSchema: {
+        type: "object",
+        properties: {
+          a: { const: "b" },
+        },
+      },
+    })
+
+    expect(sampleFromSchema(definition)).toStrictEqual('{"a":"b"}')
+  })
+
+  it("should handle contentSchema defined as type=string", function () {
+    const definition = fromJS({
+      type: "string",
+      contentMediaType: "text/plain",
+      contentSchema: {
+        type: "string",
+      },
+    })
+
+    expect(sampleFromSchema(definition)).toStrictEqual("string")
+  })
+
+  it("should handle contentSchema defined as type=number", function () {
+    const definition = fromJS({
+      type: "string",
+      contentMediaType: "text/plain",
+      contentSchema: {
+        type: "number",
+      },
+    })
+
+    expect(sampleFromSchema(definition)).toStrictEqual("0")
+  })
+
+  it("should handle contentSchema defined as type=number + contentEncoding", function () {
+    const definition = fromJS({
+      type: "string",
+      contentEncoding: "base16",
+      contentMediaType: "text/plain",
+      contentSchema: {
+        type: "number",
+      },
+    })
+
+    expect(sampleFromSchema(definition)).toStrictEqual("30")
+  })
+
   it("should handle type keyword defined as list of types", function () {
     const definition = fromJS({ type: ["object", "string"] })
     const expected = {}