diff --git a/controllers/api.js b/controllers/api.js
index c5c7b0a8..b62c2ba5 100644
--- a/controllers/api.js
+++ b/controllers/api.js
@@ -5,7 +5,12 @@ const express  = require('express')
 	, utils = require('../utils.js')
 	, Posts = require(__dirname+'/../models/posts.js')
 	, Boards = require(__dirname+'/../models/boards.js')
-	, files = require(__dirname+'/../helpers/file.js')
+	, uuidv4 = require('uuid/v4')
+	, path = require('path')
+	, fileUpload = require(__dirname+'/../helpers/file-upload.js')
+	, fileThumbnail = require(__dirname+'/../helpers/file-thumbnail.js')
+	, fileIdentify = require(__dirname+'/../helpers/file-identify.js')
+	, fileCheckMimeType = require(__dirname+'/../helpers/file-check-mime-types.js')
 
 // make new post
 router.post('/board/:board', Boards.exists, async (req, res, next) => {
@@ -23,15 +28,46 @@ router.post('/board/:board', Boards.exists, async (req, res, next) => {
 		}
 	}
 
-	let filename = '';
-	//we got a file
-	if (req.files != null && Object.keys(req.files).length > 0) {
-		try {
-			// save and thumb it
-			filename = await files.uploadAndThumb(req, res);
-		} catch (err) {
-			console.error(err);
-			return res.status(500).json({ 'message': 'Error uploading file' });
+	let files = [];
+	// check for file
+	if (req.files != null) {
+		// get names and amounc
+		const fileKeys = Object.keys(req.files);
+		const numFiles = fileKeys.length
+		// if we got a file
+		if (numFiles > 0) {
+			// check all mime types befoer we try saving anything
+			for (let i = 0; i < numFiles; i++) {
+				if (!fileCheckMimeType(req.files[fileKeys[i]].mimetype)) {
+					return res.status(400).json({ 'message': 'Invalid file type' });
+				}
+			}
+			// then upload, thumb, get metadata, etc.
+			for (let i = 0; i < numFiles; i++) {
+				const file = req.files[fileKeys[i]];
+				const filename = uuidv4() + path.extname(file.name);
+				// try to save, thumbnail and get metadata
+				try {
+					await fileUpload(req, res, filename);
+					const fileData = await fileIdentify(filename);
+					await fileThumbnail(filename);
+					files.push({
+						filename: filename,
+						originalFilename: file.name,
+						mimetype: file.mimetype,
+						size: file.size,
+						dimensions: fileData.size,
+						geometry: fileData.Geometry,
+						size: fileData.Filesize
+					})
+				} catch (err) {
+					console.error(err);
+
+					//TODO: DELETE FAILED FILES
+
+					return res.status(500).json({ 'message': 'Error uploading file' });
+				}
+			}
 		}
 	}
 
@@ -41,7 +77,7 @@ router.post('/board/:board', Boards.exists, async (req, res, next) => {
         'date': new Date(),
         'content': req.body.content,
         'thread': req.body.thread || null,
-        'file': filename
+        'files': files
     };
 
 	const post = await Posts.insertOne(req.params.board, data)
@@ -129,6 +165,19 @@ router.get('/boards', Boards.exists, async (req, res, next) => {
 
 });
 
+/*
+(async () => {
+	await Boards.deleteIncrement('b');
+	await Boards.deleteAll();
+	await Boards.insertOne({
+		_id: 'b',
+		name: 'random',
+		description: 'post anything here',
+	})
+	await Posts.deleteAll('b');
+})();
+*/
+
 /*
 (async () => {
 	await Boards.deleteIncrement('b');
diff --git a/helpers/filefilter.js b/helpers/file-check-mime-types.js
similarity index 62%
rename from helpers/filefilter.js
rename to helpers/file-check-mime-types.js
index bab1bc97..1f3736e3 100644
--- a/helpers/filefilter.js
+++ b/helpers/file-check-mime-types.js
@@ -2,4 +2,4 @@
 
 const allowedMimeTypes = new Set(['image/jpeg', 'image/pjpeg', 'image/png', 'image/gif']);
 
-module.exports = (file) => allowedMimeTypes.has(file.mimetype);
+module.exports = (mimetype) => allowedMimeTypes.has(mimetype);
diff --git a/helpers/file-identify.js b/helpers/file-identify.js
new file mode 100644
index 00000000..f3e8700e
--- /dev/null
+++ b/helpers/file-identify.js
@@ -0,0 +1,17 @@
+const gm = require('@tohru/gm')
+	, configs = require(__dirname+'/../configs/main.json')
+	, uploadDirectory = require(__dirname+'/uploadDirectory.js');
+
+module.exports = (filename) => {
+
+	return new Promise((resolve, reject) => {
+		gm(uploadDirectory + filename)
+			.identify(function (err, data) {
+				if (err) {
+					return reject(err);
+				}
+			return resolve(data)
+		});
+	});
+
+};
diff --git a/helpers/file-thumbnail.js b/helpers/file-thumbnail.js
new file mode 100644
index 00000000..c578e948
--- /dev/null
+++ b/helpers/file-thumbnail.js
@@ -0,0 +1,19 @@
+const gm = require('@tohru/gm')
+	, configs = require(__dirname+'/../configs/main.json')
+	, uploadDirectory = require(__dirname+'/uploadDirectory.js');
+
+module.exports = (filename) => {
+
+	return new Promise((resolve, reject) => {
+		gm(uploadDirectory + filename)
+			.resize(128, 128)
+			.noProfile()
+			.write(uploadDirectory + 'thumb-' + filename, function (err) {
+				if (err) {
+					return reject(err);
+				}
+			});
+		return resolve();
+	});
+
+};
diff --git a/helpers/file-upload.js b/helpers/file-upload.js
new file mode 100644
index 00000000..f4853c08
--- /dev/null
+++ b/helpers/file-upload.js
@@ -0,0 +1,18 @@
+'use strict';
+
+const configs = require(__dirname+'/../configs/main.json')
+	, uploadDirectory = require(__dirname+'/uploadDirectory.js');
+
+module.exports = (req, res, filename) => {
+
+	return new Promise((resolve, reject) => {
+		const file = req.files.file;
+		file.mv(uploadDirectory + filename, function (err) {
+			if (err) {
+				return reject(err);
+			}
+			return resolve()
+		});
+	});
+
+};
diff --git a/helpers/file.js b/helpers/file.js
deleted file mode 100644
index 7fd620f4..00000000
--- a/helpers/file.js
+++ /dev/null
@@ -1,39 +0,0 @@
-'use strict';
-const isValidFile = require(__dirname+'/filefilter.js')
-	, path = require('path')
-	, uploadDest = path.join(__dirname, '/../static/img/')
-	, uuidv4 = require('uuid/v4')
-	, gm = require('@tohru/gm');
-
-module.exports = {
-
-	uploadDest,
-
-	uploadAndThumb: (req, res) => {
-		return new Promise((resolve, reject) => {
-			const file = req.files.file;
-			//check type
-			if (!isValidFile(file)) {
-				return reject(new Error('Unsupported file type'))
-			}
-			//save it
-			const filename = uuidv4() + path.extname(file.name);
-			file.mv(uploadDest + filename, function (err) {
-				if (err) {
-					return reject(err);
-				}
-				//thumbnail it
-				gm(uploadDest + filename)
-					.resize(128, 128)
-					.noProfile()
-					.write(uploadDest + 'thumb-' + filename, function (err) {
-					if (err) {
-						return reject(err);
-					}
-					return resolve(filename);
-				});
-			});
-		});
-	},
-
-};
diff --git a/helpers/uploadDirectory.js b/helpers/uploadDirectory.js
new file mode 100644
index 00000000..c8f9f529
--- /dev/null
+++ b/helpers/uploadDirectory.js
@@ -0,0 +1,6 @@
+'use strict';
+
+const path = require('path');
+const directory = path.join(__dirname+'/../static/img/')
+
+module.exports = directory;