diff --git a/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.RequestBodies.swift b/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.RequestBodies.swift
index 7003aeb..0eaaa91 100644
--- a/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.RequestBodies.swift
+++ b/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.RequestBodies.swift
@@ -142,10 +142,31 @@ extension _Gemini.APISpecification {
             }
         }
         
-        public struct FileUploadInput: Codable, HTTPRequest.Multipart.ContentConvertible {
+        public struct FinalizeFileUploadInput {
+            public let data: Data
+            public let uploadUrl: String
+            public let fileSize: Int
+            
+            public init(data: Data, uploadUrl: String, fileSize: Int) {
+                self.data = data
+                self.uploadUrl = uploadUrl
+                self.fileSize = fileSize
+            }
+        }
+        
+        public struct StartFileUploadInput: Codable {
+            public struct UploadMetadata: Codable {
+                let file: FileMetadata
+                
+                struct FileMetadata: Codable {
+                    let display_name: String
+                }
+            }
+            
             public let fileData: Data
             public let mimeType: String
             public let displayName: String
+            public let metadata: UploadMetadata
             
             public init(
                 fileData: Data,
@@ -155,11 +176,12 @@ extension _Gemini.APISpecification {
                 self.fileData = fileData
                 self.mimeType = mimeType
                 self.displayName = displayName
+                self.metadata = .init(file: .init(display_name: displayName))
             }
-            
+            /*
             public func __conversion() throws -> HTTPRequest.Multipart.Content {
                 var result = HTTPRequest.Multipart.Content()
-                                
+                
                 // TODO: - Add this to `HTTPMediaType` @jared @vmanot
                 let fileExtension: String = {
                     guard let subtype = mimeType.split(separator: "/").last else {
@@ -188,17 +210,11 @@ extension _Gemini.APISpecification {
                     }
                 }()
                 
-                result.append(
-                    .file(
-                        named: "file",
-                        data: fileData,
-                        filename: "\(displayName).\(fileExtension)",
-                        contentType: .init(rawValue: mimeType)
-                    )
-                )
+                result.ap
                 
                 return result
             }
+            */
         }
         
         public struct DeleteFileInput: Codable {
diff --git a/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.swift b/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.swift
index fe289d0..4474386 100644
--- a/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.swift
+++ b/Sources/_Gemini/Intramodular/API/_Gemini.APISpecification.swift
@@ -75,11 +75,29 @@ extension _Gemini {
         // Initial Upload Request endpoint
         @POST
         @Path("/upload/v1beta/files")
-        @Header([
-            "X-Goog-Upload-Command": "start, upload, finalize"
-        ])
-        @Body(multipart: .input)
-        var uploadFile = Endpoint<RequestBodies.FileUploadInput, ResponseBodies.FileUpload, Void>()
+        @Header({ context in
+            [
+                HTTPHeaderField(key: "X-Goog-Upload-Protocol", value: "resumable"),
+                HTTPHeaderField(key: "X-Goog-Upload-Command", value: "start"),
+                HTTPHeaderField(key: "X-Goog-Upload-Header-Content-Length", value: "\(context.input.fileData.count)"),
+                HTTPHeaderField(key: "X-Goog-Upload-Header-Content-Type", value: context.input.mimeType),
+                HTTPHeaderField.contentType(.json)
+            ]
+        })
+        @Body(json: \RequestBodies.StartFileUploadInput.metadata)
+        var startFileUpload = Endpoint<RequestBodies.StartFileUploadInput, String, Self.Options>()
+        
+        @POST
+        @Path({ context in context.input.uploadUrl })
+        @Header({ context in
+            [
+                HTTPHeaderField(key: "Content-Length", value: "\(context.input.fileSize)"),
+                HTTPHeaderField(key: "X-Goog-Upload-Offset", value: "0"),
+                HTTPHeaderField(key: "X-Goog-Upload-Command", value: "upload, finalize")
+            ]
+        })
+        @Body(json: \RequestBodies.FinalizeFileUploadInput.data)
+        var finalizeFileUpload = Endpoint<RequestBodies.FinalizeFileUploadInput, ResponseBodies.FileUpload, Void>()
         
         // File Status endpoint
         @GET
@@ -157,6 +175,7 @@ extension _Gemini.APISpecification {
                 context: context
             )
             
+            // FIXME: (@jared) - why are you replacing the query instead of appending a new query item? is this intentional?
             if let apiKey = context.root.configuration.apiKey {
                 request = request.query([.init(name: "key", value: apiKey)])
             }
@@ -173,10 +192,34 @@ extension _Gemini.APISpecification {
             
             try response.validate()
             
+            
+            if let options: _Gemini.APISpecification.Options = context.options as? _Gemini.APISpecification.Options, let headerKey = options.outputHeaderKey {
+                print("HEADERS: \(response.headerFields)")
+                let stringValue: String? = response.headerFields.first (where: { $0.key == headerKey })?.value
+                print(stringValue)
+                
+                switch Output.self {
+                    case String.self:
+                        return (try stringValue.unwrap()) as! Output
+                    case Optional<String>.self:
+                        return stringValue as! Output
+                    default:
+                        throw _Gemini.APIError.invalidContentType
+                }
+            }
+            
             return try response.decode(
                 Output.self,
                 keyDecodingStrategy: .convertFromSnakeCase
             )
         }
     }
+    
+    public class Options {
+        var outputHeaderKey: HTTPHeaderField.Key?
+        
+        init(outputHeaderKey: HTTPHeaderField.Key? = nil) {
+            self.outputHeaderKey = outputHeaderKey
+        }
+    }
 }
diff --git a/Sources/_Gemini/Intramodular/_Gemini.Client+Files.swift b/Sources/_Gemini/Intramodular/_Gemini.Client+Files.swift
index b6fa298..7ff3c88 100644
--- a/Sources/_Gemini/Intramodular/_Gemini.Client+Files.swift
+++ b/Sources/_Gemini/Intramodular/_Gemini.Client+Files.swift
@@ -9,6 +9,17 @@ import Merge
 import NetworkKit
 import Swallow
 
+fileprivate enum TempError: CustomStringError, Error {
+    case fetchedResponse
+    
+    public var description: String {
+        switch self {
+            case .fetchedResponse:
+                return "Got response url from header"
+        }
+    }
+}
+
 extension _Gemini.Client {
     public func uploadFile(
         from data: Data,
@@ -20,27 +31,26 @@ extension _Gemini.Client {
             throw FileProcessingError.invalidFileName
         }
         
-        do {
-            var mimeType: String? = mimeType?.rawValue ?? _MediaAssetFileType(data)?.mimeType
-            
-            if mimeType == nil, let swiftType {
-                mimeType = HTTPMediaType(_swiftType: swiftType)?.rawValue
-            }
-            
-            let input = _Gemini.APISpecification.RequestBodies.FileUploadInput(
-                fileData: data,
-                mimeType: try mimeType.unwrap(),
-                displayName: displayName
-            )
-            
-            let response = try await run(\.uploadFile, with: input)
-            
-            return response.file
-        } catch {
-            throw _Gemini.APIError.unknown(message: "File upload failed: \(error.localizedDescription)")
+        var mimeType: String? = mimeType?.rawValue ?? _MediaAssetFileType(data)?.mimeType
+        
+        if mimeType == nil, let swiftType {
+            mimeType = HTTPMediaType(_swiftType: swiftType)?.rawValue
         }
+        
+        let input = _Gemini.APISpecification.RequestBodies.StartFileUploadInput(
+            fileData: data,
+            mimeType: try mimeType.unwrap(),
+            displayName: displayName
+        )
+        
+        let uploadURLString: String = try await run(\.startFileUpload, with: input, options: _Gemini.APISpecification.Options(outputHeaderKey: .custom("x-goog-upload-url"))).value
+        
+        let result: _Gemini.APISpecification.ResponseBodies.FileUpload = try await run(\.finalizeFileUpload, with: _Gemini.APISpecification.RequestBodies.FinalizeFileUploadInput(data: data, uploadUrl: uploadURLString, fileSize: data.count))
+        
+        return result.file
     }
     
+    
     public func uploadFile(
         from url: URL,
         mimeType: HTTPMediaType?,