diff --git a/assets/js/Components/FilesModal.js b/assets/js/Components/FilesModal.js
index 993e24afb..aa7e04ae5 100644
--- a/assets/js/Components/FilesModal.js
+++ b/assets/js/Components/FilesModal.js
@@ -36,6 +36,7 @@ class FilesModal extends React.Component {
     this.handleDropAccept = this.handleDropAccept.bind(this)
     this.handleDropReject = this.handleDropReject.bind(this)
     this.handleFilePost = this.handleFilePost.bind(this)
+    this.setAcceptType = this.setAcceptType.bind(this)
   }
 
   componentDidUpdate(prevProps, prevState) {
@@ -59,6 +60,46 @@ class FilesModal extends React.Component {
     return -1;
   }
 
+  setAcceptType(file) {
+    let accept = []
+
+    switch(file.fileType) {
+      case "doc":
+        accept = ["doc", "docx"]
+        break
+
+      case "ppt":
+        accept = ["ppt", "pptx"]
+        break
+
+      case "xls":
+        accept = ["xls", "xlsx"]
+        break
+
+      default:
+        accept = fileType
+        break
+    }
+
+    let extension = file.fileName.slice(-4)
+
+    switch(extension) {
+      case "xlsx":
+        accept = "xlsx"
+        break
+      
+      case "pptx":
+        accept = "pptx"
+        break
+
+      case "docx":
+        accept = "docx"
+        break
+    }
+
+    return accept
+  }
+
   // Handler for the previous and next buttons on the modal
   // Will wrap around if the index goes out of bounds
   handleFileChange(newIndex) {
@@ -80,7 +121,8 @@ class FilesModal extends React.Component {
   }
 
   render() {
-    const { activeFile } = this.props
+    let { activeFile } = this.props
+    activeFile.acceptType = this.setAcceptType(activeFile)
     let activeIndex = this.findActiveIndex()
 
     return (
@@ -121,7 +163,7 @@ class FilesModal extends React.Component {
                     <Text display="block" weight="bold">{this.props.t('label.replace')}</Text>
                     <Text as="p">{this.props.t('label.replace.desc')}</Text>
                     <FileDrop
-                      accept={activeFile.fileType}
+                      accept={activeFile.acceptType}
                       onDropAccepted={this.handleDropAccept}
                       onDropRejected={this.handleDropReject}
                       renderLabel={
diff --git a/assets/js/Components/FilesPage.js b/assets/js/Components/FilesPage.js
index 5c2217d3a..70807e2ad 100644
--- a/assets/js/Components/FilesPage.js
+++ b/assets/js/Components/FilesPage.js
@@ -328,4 +328,4 @@ class FilesPage extends React.Component {
   }
 }
 
-export default FilesPage;
\ No newline at end of file
+export default FilesPage;
diff --git a/src/Lms/Canvas/CanvasApi.php b/src/Lms/Canvas/CanvasApi.php
index 845c6601c..7415b049e 100644
--- a/src/Lms/Canvas/CanvasApi.php
+++ b/src/Lms/Canvas/CanvasApi.php
@@ -106,7 +106,7 @@ public function apiPost($url, $options, $sendAuthorized = true)
     }
 
     // Posts a file to Canvas
-    public function apiFilePost(string $url, array $options, string $filepath): LmsResponse
+    public function apiFilePost(string $url, array $options, string $filepath, string $newFileName): LmsResponse
     {
         $fileResponse = $this->apiGet($url);
         $file = $fileResponse->getContent();
@@ -114,13 +114,16 @@ public function apiFilePost(string $url, array $options, string $filepath): LmsR
         // TODO: handle failed call
 
         $endpointOptions = [
-            'name' => urldecode($file['filename']),
+            'name' => $newFileName,
             'parent_folder_id' => $file['folder_id'],
+            'content_type' => $file['content-type'],
         ];
 
         $endpointResponse = $this->apiPost($options['postUrl'], ['query' => $endpointOptions], true);
         $endpointContent = $endpointResponse->getContent();
 
+        $this->apiDelete($url);
+
         // TODO: handle failed call
 
         $formFields = $endpointContent['upload_params'];
@@ -158,4 +161,32 @@ public function apiPut($url, $options)
         return $lmsResponse;
     }
 
+    public function apiDelete($url) {
+        $lmsResponse = new LmsResponse();
+
+        if (strpos($url, 'https://') === false) {
+            $pattern = '/\/files\/\d+/';
+
+            preg_match($pattern, $url, $matches);
+    
+            $url = "https://" . $this->baseUrl . "/api/v1/" . $matches[0];
+        }
+
+        $response = $this->httpClient->request('DELETE', $url);
+
+        $lmsResponse->setResponse($response);
+
+        $content = $lmsResponse->getContent();
+        if (!empty($content['errors'])) {
+            // TODO: If error is invalid token, refresh API token and try again
+
+            foreach ($content['errors'] as $error) {
+                $lmsResponse->setError($error['message']);
+            }
+        }
+
+        return $lmsResponse;
+
+    }
+
 }
diff --git a/src/Lms/Canvas/CanvasLms.php b/src/Lms/Canvas/CanvasLms.php
index ec30a2fc9..28ca0dbeb 100644
--- a/src/Lms/Canvas/CanvasLms.php
+++ b/src/Lms/Canvas/CanvasLms.php
@@ -370,7 +370,7 @@ public function postContentItem(ContentItem $contentItem)
         return $canvasApi->apiPut($url, ['body' => $options]);
     }
 
-    public function postFileItem(FileItem $file)
+    public function postFileItem(FileItem $file, string $newFileName)
     {
         $user = $this->security->getUser();
         $apiDomain = $this->getApiDomain($user);
@@ -382,7 +382,7 @@ public function postFileItem(FileItem $file)
             'postUrl' => "courses/{$file->getCourse()->getLmsCourseId()}/files"
         ];
 
-        $fileResponse = $canvasApi->apiFilePost($url, $options, $filepath);
+        $fileResponse = $canvasApi->apiFilePost($url, $options, $filepath, $newFileName);
         $fileObj = $fileResponse->getContent();
 
         if (isset($fileObj['id'])) {
diff --git a/src/Lms/D2l/D2lLms.php b/src/Lms/D2l/D2lLms.php
index 1b403781f..055ff5229 100644
--- a/src/Lms/D2l/D2lLms.php
+++ b/src/Lms/D2l/D2lLms.php
@@ -381,7 +381,7 @@ public function updateFileItem(Course $course, $file)
         $this->entityManager->flush();
     }
 
-    public function postFileItem(FileItem $file)
+    public function postFileItem(FileItem $file, string $newFileName)
     {
         return true;
     }
diff --git a/src/Lms/LmsInterface.php b/src/Lms/LmsInterface.php
index c155114db..acc6823ed 100644
--- a/src/Lms/LmsInterface.php
+++ b/src/Lms/LmsInterface.php
@@ -17,7 +17,7 @@ public function updateCourseData(Course $course, User $user);
     public function updateFileItem(Course $course, $file);
     public function updateContentItem(ContentItem $contentItem);
     public function postContentItem(ContentItem $contentItem);
-    public function postFileItem(FileItem $file);
+    public function postFileItem(FileItem $file, string $newFileName);
     public function getOauthUri(Institution $institution, UserSession $session);
     public function getAccountData(User $user, $accountId);
     public function getCourseUrl(Course $course, User $user);
diff --git a/src/Services/LmsPostService.php b/src/Services/LmsPostService.php
index 4313d7db7..81fd0207b 100644
--- a/src/Services/LmsPostService.php
+++ b/src/Services/LmsPostService.php
@@ -76,7 +76,7 @@ public function saveFileToLms(FileItem $file, UploadedFile $uploadedFile, User $
             return;
         }
 
-        return $lms->postFileItem($file);
+        return $lms->postFileItem($file, $uploadedFile->getClientOriginalName());
     }
 
     public function replaceContent(Issue $issue, ContentItem $contentItem)
diff --git a/translations/en.json b/translations/en.json
index 91cff0119..fbc217350 100644
--- a/translations/en.json
+++ b/translations/en.json
@@ -131,6 +131,7 @@
   "msg.new_content": "Course scan complete. New content has been added.",
   "msg.sync.started": "Course scan started.",
   "msg.sync.failed": "Course scan failed. Course is missing.",
+  "msg.file.replace.file_type": "File type not accepted. Please input a file with the correct filetype.",
   "msg.sync.completed": "Course scan completed.",
   "msg.sync.course_inactive": "Course scan failed. Course is inactive.",
 
diff --git a/translations/es.json b/translations/es.json
index 6e8b3ed84..38f4863cd 100644
--- a/translations/es.json
+++ b/translations/es.json
@@ -131,6 +131,7 @@
   "msg.new_content": "Escaneo del curso completo. Se ha agregado nuevo contenido.",
   "msg.sync.started": "Se inició el escaneo del curso.",
   "msg.sync.failed": "Falló el escaneo del curso. Falta el curso.",
+  "msg.file.replace.file_type": "El tipo de archivo no es válido. Por favor aporte un archivo de tipo correcto.",
   "msg.sync.completed": "Escaneo del curso completado.",
   "msg.sync.course_inactive": "Falló el escaneo del curso. El curso está inactivo.",