diff --git a/src/core/config/defaults.js b/src/core/config/defaults.js
index b7daa8fd624..12ce768b11e 100644
--- a/src/core/config/defaults.js
+++ b/src/core/config/defaults.js
@@ -87,6 +87,13 @@ const defaultOptions = Object.freeze({
   onComplete: null,
   modelPropertyMacro: null,
   parameterMacro: null,
+
+  fileUploadMediaTypes: [
+    "application/octet-stream",
+    "image/",
+    "audio/",
+    "video/",
+  ],
 })
 
 export default defaultOptions
diff --git a/src/core/config/type-cast/mappings.js b/src/core/config/type-cast/mappings.js
index b025fb1295e..559f35025c2 100644
--- a/src/core/config/type-cast/mappings.js
+++ b/src/core/config/type-cast/mappings.js
@@ -45,6 +45,10 @@ const mappings = {
   docExpansion: { typeCaster: stringTypeCaster },
   dom_id: { typeCaster: nullableStringTypeCaster },
   domNode: { typeCaster: domNodeTypeCaster },
+  fileUploadMediaTypes: {
+    typeCaster: arrayTypeCaster,
+    defaultValue: defaultOptions.fileUploadMediaTypes,
+  },
   filter: { typeCaster: filterTypeCaster },
   fn: { typeCaster: objectTypeCaster },
   initialState: { typeCaster: objectTypeCaster },
diff --git a/src/core/plugins/json-schema-2020-12/fn.js b/src/core/plugins/json-schema-2020-12/fn.js
index 1e6626e4c56..d07f7acd4e0 100644
--- a/src/core/plugins/json-schema-2020-12/fn.js
+++ b/src/core/plugins/json-schema-2020-12/fn.js
@@ -1,6 +1,8 @@
 /**
  * @prettier
  */
+import { List, Map } from "immutable"
+
 export const upperFirst = (value) => {
   if (typeof value === "string") {
     return `${value.charAt(0).toUpperCase()}${value.slice(1)}`
@@ -504,3 +506,22 @@ export const makeGetExtensionKeywords = (fnAccessor) => {
 
   return getExtensionKeywords
 }
+
+export const hasSchemaType = (schema, type) => {
+  const isSchemaImmutable = Map.isMap(schema)
+
+  if (!isSchemaImmutable && !isPlainObject(schema)) {
+    return false
+  }
+
+  const hasType = (schemaType) =>
+    type === schemaType || (Array.isArray(type) && type.includes(schemaType))
+
+  const schemaType = isSchemaImmutable ? schema.get("type") : schema.type
+
+  if (List.isList(schemaType) || Array.isArray(schemaType)) {
+    return schemaType.some((t) => hasType(t))
+  }
+
+  return hasType(schemaType)
+}
diff --git a/src/core/plugins/json-schema-2020-12/index.js b/src/core/plugins/json-schema-2020-12/index.js
index e6c929d9fd9..c78d89dc7d2 100644
--- a/src/core/plugins/json-schema-2020-12/index.js
+++ b/src/core/plugins/json-schema-2020-12/index.js
@@ -55,6 +55,7 @@ import {
   isBooleanJSONSchema,
   getSchemaKeywords,
   makeGetExtensionKeywords,
+  hasSchemaType,
 } from "./fn"
 import { JSONSchemaPathContext, JSONSchemaLevelContext } from "./context"
 import {
@@ -143,6 +144,7 @@ const JSONSchema202012Plugin = ({ getSystem, fn }) => {
         useLevel,
         getSchemaKeywords,
         getExtensionKeywords: makeGetExtensionKeywords(fnAccessor),
+        hasSchemaType,
       },
     },
   }
diff --git a/src/core/plugins/json-schema-5/components/json-schema-components.jsx b/src/core/plugins/json-schema-5/components/json-schema-components.jsx
index 1899ffcdf68..6575a067dcd 100644
--- a/src/core/plugins/json-schema-5/components/json-schema-components.jsx
+++ b/src/core/plugins/json-schema-5/components/json-schema-components.jsx
@@ -51,6 +51,7 @@ export class JsonSchemaForm extends Component {
     const format = schema && schema.get ? schema.get("format") : null
     const type = schema && schema.get ? schema.get("type") : null
     const foldedType = fn.jsonSchema202012.foldType(immutableToJS(type))
+    const isFileUploadIntended = fn.isFileUploadIntended(schema)
 
     let getComponentSilently = (name) => getComponent(name, false, { failSilently: true })
     let Comp = type ? format ?
@@ -58,7 +59,7 @@ export class JsonSchemaForm extends Component {
       getComponentSilently(`JsonSchema_${type}`) :
       getComponent("JsonSchema_string")
 
-    if (List.isList(type) && (foldedType === "array" || foldedType === "object")) {
+    if (!isFileUploadIntended && List.isList(type) && (foldedType === "array" || foldedType === "object")) {
       Comp = getComponent("JsonSchema_object")
     }
 
diff --git a/src/core/plugins/json-schema-5/fn.js b/src/core/plugins/json-schema-5/fn.js
new file mode 100644
index 00000000000..c4844b4bcba
--- /dev/null
+++ b/src/core/plugins/json-schema-5/fn.js
@@ -0,0 +1,19 @@
+/**
+ * @prettier
+ */
+import { Map } from "immutable"
+import isPlainObject from "lodash/isPlainObject"
+
+export const hasSchemaType = (schema, type) => {
+  const isSchemaImmutable = Map.isMap(schema)
+
+  if (!isSchemaImmutable && !isPlainObject(schema)) {
+    return false
+  }
+
+  const schemaType = isSchemaImmutable ? schema.get("type") : schema.type
+
+  return (
+    type === schemaType || (Array.isArray(type) && type.includes(schemaType))
+  )
+}
diff --git a/src/core/plugins/json-schema-5/index.js b/src/core/plugins/json-schema-5/index.js
index 3aa3e375d78..f3e394a1699 100644
--- a/src/core/plugins/json-schema-5/index.js
+++ b/src/core/plugins/json-schema-5/index.js
@@ -14,6 +14,7 @@ import Schemes from "./components/schemes"
 import SchemesContainer from "./containers/schemes"
 import * as JSONSchemaComponents from "./components/json-schema-components"
 import { ModelExtensions } from "./components/model-extensions"
+import { hasSchemaType } from "./fn"
 
 const JSONSchema5Plugin = () => ({
   components: {
@@ -31,6 +32,9 @@ const JSONSchema5Plugin = () => ({
     SchemesContainer,
     ...JSONSchemaComponents,
   },
+  fn: {
+    hasSchemaType,
+  },
 })
 
 export default JSONSchema5Plugin
diff --git a/src/core/plugins/oas3/components/request-body.jsx b/src/core/plugins/oas3/components/request-body.jsx
index 7c80040be50..d7065ee04d0 100644
--- a/src/core/plugins/oas3/components/request-body.jsx
+++ b/src/core/plugins/oas3/components/request-body.jsx
@@ -105,21 +105,13 @@ const RequestBody = ({
   }
   requestBodyErrors = List.isList(requestBodyErrors) ? requestBodyErrors : List()
 
-  if(!mediaTypeValue.size) {
-    return null
-  }
-
-  const isObjectContent = mediaTypeValue.getIn(["schema", "type"]) === "object"
-  const isBinaryFormat = mediaTypeValue.getIn(["schema", "format"]) === "binary"
-  const isBase64Format = mediaTypeValue.getIn(["schema", "format"]) === "base64"
+  const isFileUploadIntended = fn.isFileUploadIntended(
+    mediaTypeValue?.get("schema"),
+    contentType
+  )
 
   if(
-    contentType === "application/octet-stream"
-    || contentType.indexOf("image/") === 0
-    || contentType.indexOf("audio/") === 0
-    || contentType.indexOf("video/") === 0
-    || isBinaryFormat
-    || isBase64Format
+    isFileUploadIntended
   ) {
     const Input = getComponent("Input")
 
@@ -132,6 +124,13 @@ const RequestBody = ({
     return <Input type={"file"} onChange={handleFile} />
   }
 
+
+  if (!mediaTypeValue.size) {
+    return null
+  }
+
+  const isObjectContent = fn.hasSchemaType(mediaTypeValue.get("schema"), "object")
+
   if (
     isObjectContent &&
     (
@@ -190,11 +189,11 @@ const RequestBody = ({
                 initialValue = JSON.parse(initialValue)
               }
 
-              const isFile = type === "string" && (format === "binary" || format === "base64")
+              const isFileUploadIntended = fn.isFileUploadIntended(schema)
 
               const jsonSchemaForm = <JsonSchemaForm
                 fn={fn}
-                dispatchInitialValue={!isFile}
+                dispatchInitialValue={!isFileUploadIntended}
                 schema={schema}
                 description={key}
                 getComponent={getComponent}
diff --git a/src/core/plugins/oas3/fn.js b/src/core/plugins/oas3/fn.js
new file mode 100644
index 00000000000..a063e4864c7
--- /dev/null
+++ b/src/core/plugins/oas3/fn.js
@@ -0,0 +1,35 @@
+/**
+ * @prettier
+ */
+import { Map } from "immutable"
+import isPlainObject from "lodash/isPlainObject"
+
+export const makeIsFileUploadIntended = (getSystem) => {
+  const isFileUploadIntended = (schema, mediaType = null) => {
+    const { getConfigs, fn } = getSystem()
+    const { fileUploadMediaTypes } = getConfigs()
+    const isFileUploadMediaType =
+      typeof mediaType === "string" &&
+      fileUploadMediaTypes.some((fileUploadMediaType) =>
+        mediaType.startsWith(fileUploadMediaType)
+      )
+
+    if (isFileUploadMediaType) {
+      return true
+    }
+
+    const isSchemaImmutable = Map.isMap(schema)
+
+    if (!isSchemaImmutable && !isPlainObject(schema)) {
+      return false
+    }
+
+    const format = isSchemaImmutable ? schema.get("format") : schema.format
+
+    return (
+      fn.hasSchemaType(schema, "string") && ["binary", "byte"].includes(format)
+    )
+  }
+
+  return isFileUploadIntended
+}
diff --git a/src/core/plugins/oas3/index.js b/src/core/plugins/oas3/index.js
index 7d63ce0e6a0..9a42d9e2ae1 100644
--- a/src/core/plugins/oas3/index.js
+++ b/src/core/plugins/oas3/index.js
@@ -9,8 +9,11 @@ import wrapComponents from "./wrap-components"
 import * as actions from "./actions"
 import * as selectors from "./selectors"
 import reducers from "./reducers"
+import { makeIsFileUploadIntended } from "./fn"
+
+export default function ({ getSystem }) {
+  const isFileUploadIntended = makeIsFileUploadIntended(getSystem)
 
-export default function () {
   return {
     components,
     wrapComponents,
@@ -28,5 +31,9 @@ export default function () {
         selectors: { ...selectors },
       },
     },
+    fn: {
+      isFileUploadIntended,
+      isFileUploadIntendedOAS30: isFileUploadIntended,
+    },
   }
 }
diff --git a/src/core/plugins/oas3/wrap-components/json-schema-string.jsx b/src/core/plugins/oas3/wrap-components/json-schema-string.jsx
index 96534b0f20b..86469396e83 100644
--- a/src/core/plugins/oas3/wrap-components/json-schema-string.jsx
+++ b/src/core/plugins/oas3/wrap-components/json-schema-string.jsx
@@ -6,14 +6,14 @@ export default OAS3ComponentWrapFactory(({ Ori, ...props }) => {
     schema,
     getComponent,
     errors,
-    onChange
+    onChange,
+    fn
   } = props
 
-  const format = schema && schema.get ? schema.get("format") : null
-  const type = schema && schema.get ? schema.get("type") : null
+  const isFileUploadIntended = fn.isFileUploadIntended(schema)
   const Input = getComponent("Input")
 
-  if(type && type === "string" && (format && (format === "binary" || format === "base64"))) {
+  if (isFileUploadIntended) {
     return <Input type="file"
                    className={ errors.length ? "invalid" : ""}
                    title={ errors.length ? errors : ""}
diff --git a/src/core/plugins/oas31/after-load.js b/src/core/plugins/oas31/after-load.js
index 68db555d5b8..b7c80032f0f 100644
--- a/src/core/plugins/oas31/after-load.js
+++ b/src/core/plugins/oas31/after-load.js
@@ -6,6 +6,7 @@ import {
   getProperties,
 } from "./json-schema-2020-12-extensions/fn"
 import { wrapOAS31Fn } from "./fn"
+import { makeIsFileUploadIntended } from "./oas3-extensions/fn"
 
 function afterLoad({ fn, getSystem }) {
   // overrides for fn.jsonSchema202012
@@ -38,6 +39,29 @@ function afterLoad({ fn, getSystem }) {
 
     Object.assign(this.fn, wrappedFns)
   }
+
+  // overrides behavior in OpenAPI 3.1.x, recognizes more intentions
+  const isFileUploadIntended = makeIsFileUploadIntended(getSystem)
+  const { isFileUploadIntended: isFileUploadIntendedWrap } = wrapOAS31Fn(
+    {
+      isFileUploadIntended,
+    },
+    getSystem()
+  )
+
+  this.fn.isFileUploadIntended = isFileUploadIntendedWrap
+  this.fn.isFileUploadIntendedOAS31 = isFileUploadIntended
+
+  if (fn.jsonSchema202012) {
+    const { hasSchemaType } = wrapOAS31Fn(
+      {
+        hasSchemaType: fn.jsonSchema202012.hasSchemaType,
+      },
+      getSystem()
+    )
+
+    this.fn.hasSchemaType = hasSchemaType
+  }
 }
 
 export default afterLoad
diff --git a/src/core/plugins/oas31/oas3-extensions/fn.js b/src/core/plugins/oas31/oas3-extensions/fn.js
new file mode 100644
index 00000000000..f032e228247
--- /dev/null
+++ b/src/core/plugins/oas31/oas3-extensions/fn.js
@@ -0,0 +1,13 @@
+/**
+ * @prettier
+ */
+
+export const makeIsFileUploadIntended = (getSystem) => {
+  const isFileUploadIntended = (schema, mediaType = null) => {
+    const { fn } = getSystem()
+
+    return fn.isFileUploadIntendedOAS30(schema, mediaType)
+  }
+
+  return isFileUploadIntended
+}
diff --git a/test/e2e-cypress/e2e/features/plugins/oas3/request-body-upload-file.cy.js b/test/e2e-cypress/e2e/features/plugins/oas3/request-body-upload-file.cy.js
new file mode 100644
index 00000000000..c5827b59432
--- /dev/null
+++ b/test/e2e-cypress/e2e/features/plugins/oas3/request-body-upload-file.cy.js
@@ -0,0 +1,189 @@
+/**
+ * @prettier
+ */
+
+describe("OpenAPI 3.0 Request Body upload file button", () => {
+  beforeEach(() => {
+    cy.visit("/?url=/documents/features/oas3-request-body-upload-file.yaml")
+  })
+
+  describe("application/octet-stream", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadApplicationOctetStream").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/octet-stream media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("image/png", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadImagePng").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for image/png media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("audio/wav", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadAudioWav").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for audio/wav media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("video/mpeg", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadVideoMpeg").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for video/mpeg media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("application/octet-stream with empty Media Type Object", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadApplicationOctetStreamEmpty").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/octet-stream media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("schema type string and format binary", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadSchemaFormatBinary").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/x-custom media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("schema type string and format byte", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadSchemaFormatByte").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/x-custom media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("multipart/form-data object property with schema type string and format binary", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadPropertySchemaFormatBinary").click()
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("multipart/form-data object property with schema type string and format byte", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadPropertySchemaFormatByte").click()
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+})
diff --git a/test/e2e-cypress/e2e/features/plugins/oas31/oas31-request-body-upload-file.cy.js b/test/e2e-cypress/e2e/features/plugins/oas31/oas31-request-body-upload-file.cy.js
new file mode 100644
index 00000000000..4d1f9a254aa
--- /dev/null
+++ b/test/e2e-cypress/e2e/features/plugins/oas31/oas31-request-body-upload-file.cy.js
@@ -0,0 +1,257 @@
+/**
+ * @prettier
+ */
+
+describe("OpenAPI 3.1 Request Body upload file button", () => {
+  beforeEach(() => {
+    cy.visit("/?url=/documents/features/oas31-request-body-upload-file.yaml")
+  })
+
+  describe("application/octet-stream", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadApplicationOctetStream").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/octet-stream media types."
+      )
+    })
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("image/png", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadImagePng").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for image/png media types."
+      )
+    })
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("audio/wav", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadAudioWav").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for audio/wav media types."
+      )
+    })
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("video/mpeg", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadVideoMpeg").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for video/mpeg media types."
+      )
+    })
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("application/octet-stream with empty Media Type Object", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadApplicationOctetStreamEmpty").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/octet-stream media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("schema type string and format binary", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadSchemaTypeFormatBinary").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/x-custom media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("schema type string and format byte", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadSchemaTypeFormatByte").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/x-custom media types."
+      )
+    })
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("schema union type includes string and format binary", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadSchemaUnionTypeFormatBinary").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/x-custom media types."
+      )
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("schema union type includes string and format byte", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadSchemaUnionTypeFormatByte").click()
+    })
+
+    it("should display description with the correct content type", () => {
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper i"
+      ).should(
+        "have.text",
+        "Example values are not available for application/x-custom media types."
+      )
+    })
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("multipart/form-data object property with schema type string and format binary", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadPropertySchemaFormatBinary").click()
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("multipart/form-data object property with schema type string and format byte", () => {
+    beforeEach(() => {
+      cy.get("#operations-default-uploadPropertySchemaFormatByte").click()
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("multipart/form-data object property with schema union type including string and format binary", () => {
+    beforeEach(() => {
+      cy.get(
+        "#operations-default-uploadPropertySchemaUnionTypeFormatBinary"
+      ).click()
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+
+  describe("multipart/form-data object property with schema union type including string and format byte", () => {
+    beforeEach(() => {
+      cy.get(
+        "#operations-default-uploadPropertySchemaUnionTypeFormatByte"
+      ).click()
+    })
+
+    it("should display a file upload button", () => {
+      cy.get(".try-out__btn").click()
+      cy.get(
+        ".opblock-section-request-body .opblock-description-wrapper input"
+      ).should("have.prop", "type", "file")
+    })
+  })
+})
diff --git a/test/e2e-cypress/e2e/features/request-body-upload-file.cy.js b/test/e2e-cypress/e2e/features/request-body-upload-file.cy.js
deleted file mode 100644
index bb0819f92dc..00000000000
--- a/test/e2e-cypress/e2e/features/request-body-upload-file.cy.js
+++ /dev/null
@@ -1,132 +0,0 @@
-/**
- * @prettier
- */
-
-describe("OpenAPI 3.0 Request Body upload file button", () => {
-  describe("application/octet-stream", () => {
-    it("should display description with the correct content type", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadApplicationOctetStream")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper i")
-        .should(
-          "have.text",
-          "Example values are not available for application/octet-stream media types."
-        )
-    })
-    it("should display a file upload button", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadApplicationOctetStream")
-        .click()
-        .get(".try-out__btn")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper input")
-        .should("have.prop", "type", "file")
-    })
-  })
-  describe("image/png", () => {
-    it("should display description with the correct content type", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadImagePng")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper i")
-        .should(
-          "have.text",
-          "Example values are not available for image/png media types."
-        )
-    })
-    it("should display a file upload button", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadApplicationOctetStream")
-        .click()
-        .get(".try-out__btn")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper input")
-        .should("have.prop", "type", "file")
-    })
-  })
-  describe("audio/wav", () => {
-    it("should display description with the correct content type", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadAudioWav")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper i")
-        .should(
-          "have.text",
-          "Example values are not available for audio/wav media types."
-        )
-    })
-    it("should display a file upload button", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadApplicationOctetStream")
-        .click()
-        .get(".try-out__btn")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper input")
-        .should("have.prop", "type", "file")
-    })
-  })
-  describe("video/mpeg", () => {
-    it("should display description with the correct content type", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadVideoMpeg")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper i")
-        .should(
-          "have.text",
-          "Example values are not available for video/mpeg media types."
-        )
-    })
-    it("should display a file upload button", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadApplicationOctetStream")
-        .click()
-        .get(".try-out__btn")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper input")
-        .should("have.prop", "type", "file")
-    })
-  })
-  describe("schema format binary", () => {
-    it("should display description with the correct content type", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadSchemaFormatBinary")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper i")
-        .should(
-          "have.text",
-          "Example values are not available for application/x-custom media types."
-        )
-    })
-    it("should display a file upload button", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadSchemaFormatBinary")
-        .click()
-        .get(".try-out__btn")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper input")
-        .should("have.prop", "type", "file")
-    })
-  })
-  describe("schema format base64", () => {
-    it("should display description with the correct content type", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadSchemaFormatBase64")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper i")
-        .should(
-          "have.text",
-          "Example values are not available for application/x-custom media types."
-        )
-    })
-    it("should display a file upload button", () => {
-      cy.visit("/?url=/documents/features/request-body-upload-file.yaml")
-        .get("#operations-default-uploadSchemaFormatBinary")
-        .click()
-        .get(".try-out__btn")
-        .click()
-        .get(".opblock-section-request-body .opblock-description-wrapper input")
-        .should("have.prop", "type", "file")
-    })
-  })
-})
diff --git a/test/e2e-cypress/static/documents/features/request-body-upload-file.yaml b/test/e2e-cypress/static/documents/features/oas3-request-body-upload-file.yaml
similarity index 53%
rename from test/e2e-cypress/static/documents/features/request-body-upload-file.yaml
rename to test/e2e-cypress/static/documents/features/oas3-request-body-upload-file.yaml
index 2c487da298c..619a5095a14 100644
--- a/test/e2e-cypress/static/documents/features/request-body-upload-file.yaml
+++ b/test/e2e-cypress/static/documents/features/oas3-request-body-upload-file.yaml
@@ -7,8 +7,11 @@ info:
     * `audio/*` content type (no matter what schema format)
     * `image/*` content type (no matter what schema format)
     * `video/*` content type (no matter what schema format)
-    * schema format is `base64` (no matter what content type)
-    * schema format is `binary` (no matter what content type)
+    * `application/octect-stream` content type with empty Media Type Object
+    * schema type is `string` and format is `byte` (no matter what content type)
+    * schema type is `string` and format is `binary` (no matter what content type)
+    * multipart/form-data object property schema type is `string` and format is `byte`
+    * multipart/form-data object property schema type is `string` and format is `binary`
   version: "1.0.0"
 paths:
   /upload-application-octet-stream:
@@ -19,13 +22,6 @@ paths:
           application/octet-stream:
             schema:
               type: string
-      responses:
-        '200':
-          description: successful operation
-          content:
-            text/plain:
-              schema:
-                type: string
   /upload-image-png:
     post:
       operationId: uploadImagePng
@@ -34,13 +30,6 @@ paths:
           image/png:
             schema:
               type: string
-      responses:
-        '200':
-          description: successful operation
-          content:
-            text/plain:
-              schema:
-                type: string
   /upload-audio-wav:
     post:
       operationId: uploadAudioWav
@@ -49,13 +38,6 @@ paths:
           audio/wav:
             schema:
               type: string
-      responses:
-        '200':
-          description: successful operation
-          content:
-            text/plain:
-              schema:
-                type: string
   /upload-video-mpeg:
     post:
       operationId: uploadVideoMpeg
@@ -64,13 +46,12 @@ paths:
           video/mpeg:
             schema:
               type: string
-      responses:
-        '200':
-          description: successful operation
-          content:
-            text/plain:
-              schema:
-                type: string
+  /upload-application-octet-stream-empty:
+    post:
+      operationId: uploadApplicationOctetStreamEmpty
+      requestBody:
+        content:
+          application/octet-stream: {}
   /upload-schema-format-binary:
     post:
       operationId: uploadSchemaFormatBinary
@@ -80,26 +61,36 @@ paths:
             schema:
               type: string
               format: binary
-      responses:
-        '200':
-          description: successful operation
-          content:
-            text/plain:
-              schema:
-                type: string
-  /upload-schema-format-base64:
+  /upload-schema-format-byte:
     post:
-      operationId: uploadSchemaFormatBase64
+      operationId: uploadSchemaFormatByte
       requestBody:
         content:
           application/x-custom:
             schema:
               type: string
-              format: base64
-      responses:
-        '200':
-          description: successful operation
-          content:
-            text/plain:
-              schema:
-                type: string
+              format: byte
+  /upload-property-schema-format-binary:
+    post:
+      operationId: uploadPropertySchemaFormatBinary
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: binary
+  /upload-property-schema-format-byte:
+    post:
+      operationId: uploadPropertySchemaFormatByte
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: byte
diff --git a/test/e2e-cypress/static/documents/features/oas31-request-body-upload-file.yaml b/test/e2e-cypress/static/documents/features/oas31-request-body-upload-file.yaml
new file mode 100644
index 00000000000..85c04608eef
--- /dev/null
+++ b/test/e2e-cypress/static/documents/features/oas31-request-body-upload-file.yaml
@@ -0,0 +1,150 @@
+openapi: 3.1.0
+info:
+  title: "Request body file upload"
+  description: |-
+    This document has examples for examining the `schema` or content type for request bodies requiring a file upload
+    * `application/octect-stream` content type (no matter what schema format)
+    * `audio/*` content type (no matter what schema format)
+    * `image/*` content type (no matter what schema format)
+    * `video/*` content type (no matter what schema format)
+    * `application/octect-stream` content type with empty Media Type Object
+    * schema type is `string` and format is `byte` (no matter what content type)
+    * schema type is `string` and format is `binary` (no matter what content type)
+    * schema union type includes `string` and format is `byte` (no matter what content type)
+    * schema union type includes `string` and format is `binary` (no matter what content type)
+    * multipart/form-data object property schema type is `string` and format is `byte`
+    * multipart/form-data object property schema type is `string` and format is `binary`
+    * multipart/form-data object property schema union type includes `string` and format is `byte`
+    * multipart/form-data object property schema union type includes `string` and format is `binary`
+  version: "1.0.0"
+paths:
+  /upload-application-octet-stream:
+    post:
+      operationId: uploadApplicationOctetStream
+      requestBody:
+        content:
+          application/octet-stream:
+            schema:
+              type: string
+  /upload-image-png:
+    post:
+      operationId: uploadImagePng
+      requestBody:
+        content:
+          image/png:
+            schema:
+              type: string
+  /upload-audio-wav:
+    post:
+      operationId: uploadAudioWav
+      requestBody:
+        content:
+          audio/wav:
+            schema:
+              type: string
+  /upload-video-mpeg:
+    post:
+      operationId: uploadVideoMpeg
+      requestBody:
+        content:
+          video/mpeg:
+            schema:
+              type: string
+  /upload-application-octet-stream-empty:
+    post:
+      operationId: uploadApplicationOctetStreamEmpty
+      requestBody:
+        content:
+          application/octet-stream: {}
+  /upload-schema-type-format-binary:
+    post:
+      operationId: uploadSchemaTypeFormatBinary
+      requestBody:
+        content:
+          application/x-custom:
+            schema:
+              type: string
+              format: binary
+  /upload-schema-type-format-byte:
+    post:
+      operationId: uploadSchemaTypeFormatByte
+      requestBody:
+        content:
+          application/x-custom:
+            schema:
+              type: string
+              format: byte
+  /upload-schema-union-type-format-binary:
+    post:
+      operationId: uploadSchemaUnionTypeFormatBinary
+      requestBody:
+        content:
+          application/x-custom:
+            schema:
+              type: 
+                - object
+                - string
+              format: binary
+  /upload-schema-union-type-format-byte:
+    post:
+      operationId: uploadSchemaUnionTypeFormatByte
+      requestBody:
+        content:
+          application/x-custom:
+            schema:
+              type:
+                - object
+                - string
+              format: byte
+  /upload-property-schema-format-binary:
+    post:
+      operationId: uploadPropertySchemaFormatBinary
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: binary
+  /upload-property-schema-format-byte:
+    post:
+      operationId: uploadPropertySchemaFormatByte
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: binary
+  /upload-property-schema-union-type-format-binary:
+    post:
+      operationId: uploadPropertySchemaUnionTypeFormatBinary
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type:
+                    - object 
+                    - string
+                  format: binary
+  /upload-property-schema-union-type-format-byte:
+    post:
+      operationId: uploadPropertySchemaUnionTypeFormatByte
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type:
+                    - object 
+                    - string
+                  format: byte
diff --git a/test/unit/core/plugins/json-schema-5/components/json-schema-form.jsx b/test/unit/core/plugins/json-schema-5/components/json-schema-form.jsx
index 73d0d2292a3..4600beb0784 100644
--- a/test/unit/core/plugins/json-schema-5/components/json-schema-form.jsx
+++ b/test/unit/core/plugins/json-schema-5/components/json-schema-form.jsx
@@ -4,6 +4,7 @@ import { Select, Input, TextArea } from "core/components/layout-utils"
 import { mount, render } from "enzyme"
 import * as JsonSchemaComponents from "core/plugins/json-schema-5/components/json-schema-components"
 import { foldType } from "core/plugins/json-schema-2020-12-samples/fn/index"
+import { makeIsFileUploadIntended } from "core/plugins/oas3/fn"
 
 const components = {...JsonSchemaComponents, Select, Input, TextArea}
 
@@ -13,6 +14,16 @@ const getComponentStub = (name) => {
   return null
 }
 
+const getSystemStub = () => ({
+  getConfigs: () => ({
+    fileUploadMediaTypes: [],
+  }),
+  fn: {
+    hasSchemaType: () => {},
+    isFileUploadIntendedOAS30: () => {},
+  },
+})
+
 describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
   describe("strings", function() {
     it("should render the correct options for a string enum parameter", function(){
@@ -26,6 +37,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "string",
@@ -53,6 +65,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "string",
@@ -78,6 +91,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         required: true,
         schema: Immutable.fromJS({
@@ -106,6 +120,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "boolean"
@@ -133,6 +148,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "boolean",
@@ -160,6 +176,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "boolean",
@@ -188,6 +205,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         required: true,
         schema: Immutable.fromJS({
@@ -219,6 +237,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         errors: List(),
         schema: Immutable.fromJS({
@@ -252,6 +271,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "NotARealType"
@@ -278,6 +298,7 @@ describe("<JsonSchemaComponents.JsonSchemaForm/>", function(){
           jsonSchema202012: {
             foldType,
           },
+          isFileUploadIntended: makeIsFileUploadIntended(getSystemStub)
         },
         schema: Immutable.fromJS({
           type: "NotARealType",