diff --git a/package.json b/package.json
index 5068d23e..0fe29f9f 100644
--- a/package.json
+++ b/package.json
@@ -8,9 +8,9 @@
   "license": "MIT",
   "type": "module",
   "scripts": {
-    "download": "node scripts/download",
-    "generate-types": "node scripts/generate-types",
-    "update-package": "node scripts/update-package",
+    "download": "node scripts/download.js",
+    "generate-types": "node scripts/generate-types.js",
+    "update-package": "node scripts/update-package.js",
     "lint": "prettier --check '*.{md,json}' 'scripts/*.js' 'packages/**/*.{ts,md,json,d.ts}'",
     "lint:fix": "prettier --write '*.{md,json}' 'scripts/*.js' 'packages/**/*.{ts,md,json,d.ts}'"
   },
diff --git a/packages/openapi-types-ghec/types.d.ts b/packages/openapi-types-ghec/types.d.ts
index e9e89985..28b3523d 100644
--- a/packages/openapi-types-ghec/types.d.ts
+++ b/packages/openapi-types-ghec/types.d.ts
@@ -126354,7 +126354,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/packages/openapi-types-ghes-3.14/types.d.ts b/packages/openapi-types-ghes-3.14/types.d.ts
index 5dcc86f3..9a4663d0 100644
--- a/packages/openapi-types-ghes-3.14/types.d.ts
+++ b/packages/openapi-types-ghes-3.14/types.d.ts
@@ -104161,7 +104161,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/packages/openapi-types-ghes-3.15/types.d.ts b/packages/openapi-types-ghes-3.15/types.d.ts
index f764302c..68e290b7 100644
--- a/packages/openapi-types-ghes-3.15/types.d.ts
+++ b/packages/openapi-types-ghes-3.15/types.d.ts
@@ -104990,7 +104990,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/packages/openapi-types-ghes-3.16/types.d.ts b/packages/openapi-types-ghes-3.16/types.d.ts
index 030a0190..8844c256 100644
--- a/packages/openapi-types-ghes-3.16/types.d.ts
+++ b/packages/openapi-types-ghes-3.16/types.d.ts
@@ -106446,7 +106446,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/packages/openapi-types-ghes-3.17/types.d.ts b/packages/openapi-types-ghes-3.17/types.d.ts
index e0d510a8..56b034ab 100644
--- a/packages/openapi-types-ghes-3.17/types.d.ts
+++ b/packages/openapi-types-ghes-3.17/types.d.ts
@@ -106730,7 +106730,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/packages/openapi-types-ghes-3.18/types.d.ts b/packages/openapi-types-ghes-3.18/types.d.ts
index c947e459..678545e7 100644
--- a/packages/openapi-types-ghes-3.18/types.d.ts
+++ b/packages/openapi-types-ghes-3.18/types.d.ts
@@ -107812,7 +107812,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/packages/openapi-types/types.d.ts b/packages/openapi-types/types.d.ts
index 556b0906..5e8ef94e 100644
--- a/packages/openapi-types/types.d.ts
+++ b/packages/openapi-types/types.d.ts
@@ -114946,7 +114946,7 @@ export interface operations {
     };
     requestBody?: {
       content: {
-        "application/octet-stream": string;
+        "application/octet-stream": string | File | Uint8Array | Blob;
       };
     };
     responses: {
diff --git a/scripts/generate-types.js b/scripts/generate-types.js
index 98d5c716..32b71724 100644
--- a/scripts/generate-types.js
+++ b/scripts/generate-types.js
@@ -85,9 +85,25 @@ type Repository = components["schemas"]["full-repository"]
 
     await copyFile("LICENSE", `packages/${packageName}/LICENSE`);
 
+    const schemaTS = await openapiTS(`cache/${name}.json`, {
+      transform(schemaObject, metadata) {
+        if (
+          schemaObject.format === "binary" &&
+          metadata.path.endsWith("application/octet-stream")
+        ) {
+          // Make sure that file upload endpoints don't use 'string' type for binary data
+          // Use some common types that can represent binary data in various environments
+          return schemaObject.nullable
+            ? "string | File | Uint8Array | Blob | null"
+            : "string | File | Uint8Array | Blob";
+        }
+        return undefined;
+      },
+    });
+
     await writeFile(
       `packages/${packageName}/types.d.ts`,
-      await prettier.format(await openapiTS(`cache/${name}.json`), {
+      await prettier.format(schemaTS, {
         parser: "typescript",
       }),
     );