diff --git a/delete.go b/delete.go
index 64b17ef..521b277 100644
--- a/delete.go
+++ b/delete.go
@@ -35,7 +35,7 @@ func deleteHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 		metaDelErr := os.Remove(metaPath)
 
 		if (fileDelErr != nil) || (metaDelErr != nil) {
-			oopsHandler(c, w, r) // 500 - can't delete something
+			oopsHandler(c, w, r, RespPLAIN, "Could not delete")
 			return
 		}
 
diff --git a/display.go b/display.go
index f40bc5a..5fc26c7 100644
--- a/display.go
+++ b/display.go
@@ -91,6 +91,6 @@ func fileDisplayHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	}, w)
 
 	if err != nil {
-		oopsHandler(c, w, r)
+		oopsHandler(c, w, r, RespHTML, "")
 	}
 }
diff --git a/fileserve.go b/fileserve.go
index 8097bfd..b568ce3 100644
--- a/fileserve.go
+++ b/fileserve.go
@@ -38,7 +38,7 @@ func staticHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 		filePath := strings.TrimPrefix(path, "/static/")
 		file, err := staticBox.Open(filePath)
 		if err != nil {
-			oopsHandler(c, w, r)
+			notFoundHandler(c, w, r)
 			return
 		}
 
diff --git a/pages.go b/pages.go
index c20e1b8..c4676a4 100644
--- a/pages.go
+++ b/pages.go
@@ -1,12 +1,24 @@
 package main
 
 import (
+	"encoding/json"
+	"fmt"
 	"net/http"
+	"strings"
 
 	"github.com/flosch/pongo2"
 	"github.com/zenazn/goji/web"
 )
 
+type RespType int
+
+const (
+	RespPLAIN RespType = iota
+	RespJSON
+	RespHTML
+	RespAUTO
+)
+
 func indexHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	err := Templates["index.html"].ExecuteWriter(pongo2.Context{}, w)
 	if err != nil {
@@ -17,7 +29,7 @@ func indexHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 func pasteHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	err := Templates["paste.html"].ExecuteWriter(pongo2.Context{}, w)
 	if err != nil {
-		oopsHandler(c, w, r)
+		oopsHandler(c, w, r, RespHTML, "")
 	}
 }
 
@@ -25,15 +37,41 @@ func notFoundHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	w.WriteHeader(404)
 	err := Templates["404.html"].ExecuteWriter(pongo2.Context{}, w)
 	if err != nil {
-		oopsHandler(c, w, r)
+		oopsHandler(c, w, r, RespHTML, "")
 	}
 }
 
-func oopsHandler(c web.C, w http.ResponseWriter, r *http.Request) {
-	w.WriteHeader(500)
-	err := Templates["oops.html"].ExecuteWriter(pongo2.Context{}, w)
-	if err != nil {
-		oopsHandler(c, w, r)
+func oopsHandler(c web.C, w http.ResponseWriter, r *http.Request, rt RespType, msg string) {
+	if msg == "" {
+		msg = "Oops! Something went wrong..."
+	}
+
+	if rt == RespHTML {
+		Templates["oops.html"].ExecuteWriter(pongo2.Context{"msg": msg}, w)
+		w.WriteHeader(500)
+		return
+
+	} else if rt == RespPLAIN {
+		fmt.Fprintf(w, "%s", msg)
+		w.WriteHeader(500)
+		return
+
+	} else if rt == RespJSON {
+		js, _ := json.Marshal(map[string]string{
+			"error": msg,
+		})
+
+		w.Header().Set("Content-Type", "application/json; charset=UTF-8")
+		w.WriteHeader(500)
+		w.Write(js)
+		return
+
+	} else if rt == RespAUTO {
+		if strings.EqualFold("application/json", r.Header.Get("Accept")) {
+			oopsHandler(c, w, r, RespJSON, msg)
+		} else {
+			oopsHandler(c, w, r, RespHTML, msg)
+		}
 	}
 }
 
diff --git a/server_test.go b/server_test.go
index 19a189a..31e690b 100644
--- a/server_test.go
+++ b/server_test.go
@@ -136,8 +136,8 @@ func TestPutEmptyUpload(t *testing.T) {
 
 	goji.DefaultMux.ServeHTTP(w, req)
 
-	if !strings.Contains(w.Body.String(), "Oops! Something went wrong.") {
-		t.Fatal("Response doesn't contain'Oops! Something went wrong.'")
+	if !strings.Contains(w.Body.String(), "Empty file") {
+		t.Fatal("Response doesn't contain'Empty file'")
 	}
 }
 
diff --git a/static/js/upload.js b/static/js/upload.js
index 44afffc..6c6dc62 100644
--- a/static/js/upload.js
+++ b/static/js/upload.js
@@ -58,15 +58,15 @@ Dropzone.options.dropzone = {
 			xhr.send();
 		}.bind(this);
 	},
-	error: function(file, errMsg, xhrO) {
+	error: function(file, resp, xhrO) {
 		file.rightLeftElement.onclick = null;
 		file.rightLeftElement.innerHTML = "";
 		file.rightRightElement.innerHTML = "";
 		if (file.status === "canceled") {
-			file.leftElement.innerHTML = "Canceled " + file.name;			
+			file.leftElement.innerHTML = file.name + ": Canceled ";			
 		}
 		else {
-			file.leftElement.innerHTML = "Could not upload " + file.name;
+			file.leftElement.innerHTML = file.name + ": " + resp.error;
 		}
 		file.leftElement.className = "error";
 	},
diff --git a/templates/oops.html b/templates/oops.html
index 9627bba..41dfd8f 100644
--- a/templates/oops.html
+++ b/templates/oops.html
@@ -3,7 +3,7 @@
 {% block content %}
 <div id="main">
     <div id='inner_content' style='width: 400px'>
-    	<p>{{ error_message|default:"Oops! Something went wrong." }}</p>
+    	<p>{{ msg }}</p>
     </div>
 </div>
 {% endblock %}
diff --git a/torrent.go b/torrent.go
index 01176aa..1f8c942 100644
--- a/torrent.go
+++ b/torrent.go
@@ -87,7 +87,7 @@ func fileTorrentHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 
 	encoded, err := createTorrent(fileName, filePath)
 	if err != nil {
-		oopsHandler(c, w, r) // 500 - creating torrent failed
+		oopsHandler(c, w, r, RespHTML, "Could not create torrent.")
 		return
 	}
 
diff --git a/upload.go b/upload.go
index edc4742..39f62ce 100644
--- a/upload.go
+++ b/upload.go
@@ -46,7 +46,7 @@ func uploadPostHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	if strings.HasPrefix(contentType, "multipart/form-data") {
 		file, headers, err := r.FormFile("file")
 		if err != nil {
-			oopsHandler(c, w, r)
+			oopsHandler(c, w, r, RespHTML, "Could not upload file.")
 			return
 		}
 		defer file.Close()
@@ -60,7 +60,7 @@ func uploadPostHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 		upReq.filename = headers.Filename
 	} else {
 		if r.FormValue("content") == "" {
-			oopsHandler(c, w, r)
+			oopsHandler(c, w, r, RespHTML, "Could not upload file.")
 			return
 		}
 		extension := r.FormValue("extension")
@@ -74,16 +74,22 @@ func uploadPostHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	}
 
 	upload, err := processUpload(upReq)
-	if err != nil {
-		oopsHandler(c, w, r)
-		return
-	}
 
 	if strings.EqualFold("application/json", r.Header.Get("Accept")) {
+		if err != nil {
+			oopsHandler(c, w, r, RespJSON, "Could not upload file: "+err.Error())
+			return
+		}
+
 		js := generateJSONresponse(upload)
 		w.Header().Set("Content-Type", "application/json; charset=UTF-8")
 		w.Write(js)
 	} else {
+		if err != nil {
+			oopsHandler(c, w, r, RespHTML, "Could not upload file: "+err.Error())
+			return
+		}
+
 		http.Redirect(w, r, "/"+upload.Filename, 301)
 	}
 
@@ -98,16 +104,22 @@ func uploadPutHandler(c web.C, w http.ResponseWriter, r *http.Request) {
 	upReq.src = r.Body
 
 	upload, err := processUpload(upReq)
-	if err != nil {
-		oopsHandler(c, w, r)
-		return
-	}
 
 	if strings.EqualFold("application/json", r.Header.Get("Accept")) {
+		if err != nil {
+			oopsHandler(c, w, r, RespJSON, "Could not upload file: "+err.Error())
+			return
+		}
+
 		js := generateJSONresponse(upload)
 		w.Header().Set("Content-Type", "application/json; charset=UTF-8")
 		w.Write(js)
 	} else {
+		if err != nil {
+			oopsHandler(c, w, r, RespPLAIN, "Could not upload file: "+err.Error())
+			return
+		}
+
 		fmt.Fprintf(w, Config.siteURL+upload.Filename)
 	}
 }
@@ -123,7 +135,7 @@ func uploadRemote(c web.C, w http.ResponseWriter, r *http.Request) {
 
 	resp, err := http.Get(grabUrl.String())
 	if err != nil {
-		oopsHandler(c, w, r)
+		oopsHandler(c, w, r, RespAUTO, "Could not retrieve URL")
 		return
 	}
 
@@ -131,16 +143,22 @@ func uploadRemote(c web.C, w http.ResponseWriter, r *http.Request) {
 	upReq.src = resp.Body
 
 	upload, err := processUpload(upReq)
-	if err != nil {
-		oopsHandler(c, w, r)
-		return
-	}
 
 	if strings.EqualFold("application/json", r.Header.Get("Accept")) {
+		if err != nil {
+			oopsHandler(c, w, r, RespJSON, "Could not upload file: "+err.Error())
+			return
+		}
+
 		js := generateJSONresponse(upload)
 		w.Header().Set("Content-Type", "application/json; charset=UTF-8")
 		w.Write(js)
 	} else {
+		if err != nil {
+			oopsHandler(c, w, r, RespHTML, "Could not upload file: "+err.Error())
+			return
+		}
+
 		http.Redirect(w, r, "/"+upload.Filename, 301)
 	}
 }
@@ -174,8 +192,8 @@ func processUpload(upReq UploadRequest) (upload Upload, err error) {
 		// Pull the first 512 bytes off for use in MIME detection
 		header = make([]byte, 512)
 		n, err := upReq.src.Read(header)
-		if n == 0 {
-			return upload, err
+		if n == 0 || err != nil {
+			return upload, errors.New("Empty file")
 		}
 		header = header[:n]
 
@@ -228,12 +246,15 @@ func processUpload(upReq UploadRequest) (upload Upload, err error) {
 	metadataWrite(upload.Filename, &upload)
 
 	bytes, err := io.Copy(dst, io.MultiReader(bytes.NewReader(header), upReq.src))
-	if err != nil {
-		return
-	} else if bytes == 0 {
+	if bytes == 0 {
 		os.Remove(path.Join(Config.filesDir, upload.Filename))
 		os.Remove(path.Join(Config.metaDir, upload.Filename))
 		return upload, errors.New("Empty file")
+
+	} else if err != nil {
+		os.Remove(path.Join(Config.filesDir, upload.Filename))
+		os.Remove(path.Join(Config.metaDir, upload.Filename))
+		return
 	}
 
 	upload.Size = bytes