diff --git a/static/directives/config/config-file-field.html b/static/directives/config/config-file-field.html
index cdb1b6df4..11c4227f7 100644
--- a/static/directives/config/config-file-field.html
+++ b/static/directives/config/config-file-field.html
@@ -1,7 +1,10 @@
 <div class="config-file-field-element">
   <span ng-show="uploadProgress == null">
-    <span ng-if="hasFile"><code>{{ filename }}</code></span>
-    <span class="nofile" ng-if="!hasFile && skipCheckFile != 'true'"><code>{{ filename }}</code> not found in mounted config directory: </span>
+    <span ng-if="hasFile">
+        <code>/conf/stack/{{ filename }}</code>
+        <span style="margin-left: 20px; display: inline-block;">Select a replacement file:</span>
+    </span>
+    <span class="nofile" ng-if="!hasFile && skipCheckFile != 'true'">Please select a file to upload as <b>{{ filename }}</b>: </span>
     <input type="file" ng-file-select="onFileSelect($files)">
   </span>
   <span ng-show="uploadProgress != null">
diff --git a/static/directives/config/config-setup-tool.html b/static/directives/config/config-setup-tool.html
index a36d08416..7e67107cd 100644
--- a/static/directives/config/config-setup-tool.html
+++ b/static/directives/config/config-setup-tool.html
@@ -112,7 +112,7 @@
                  A valid SSL certificate and private key files are required to use this option.
               </div>
 
-              <div class="co-alert co-alert-info" ng-if="config.PREFERRED_URL_SCHEME == 'https'">
+              <div class="co-alert co-alert-info" ng-if="config.PREFERRED_URL_SCHEME == 'https'" style="margin-bottom: 20px">
                 Enabling SSL also enables <a href="https://en.wikipedia.org/wiki/HTTP_Strict_Transport_Security">HTTP Strict Transport Security</a>.<br/>
                 This prevents downgrade attacks and cookie theft, but browsers will reject all future insecure connections on this hostname.
               </div>
@@ -121,7 +121,7 @@
                 <tr>
                   <td class="non-input">Certificate:</td>
                   <td>
-                    <span class="config-file-field" filename="ssl.cert"></span>
+                    <span class="config-file-field" filename="ssl.cert" has-file="hasfile.SSLCert"></span>
                     <div class="help-text">
                       The certificate must be in PEM format.
                     </div
@@ -130,7 +130,7 @@
                 <tr>
                   <td class="non-input">Private key:</td>
                   <td>
-                    <span class="config-file-field" filename="ssl.key"></span>
+                    <span class="config-file-field" filename="ssl.key" has-file="hasfile.SSLKey"></span>
                   </td>
                 </tr>
               </table>
@@ -487,7 +487,7 @@
           <tr>
             <td>Public Key:</td>
             <td>
-              <span class="config-file-field" filename="jwt-authn.cert"></span>
+              <span class="config-file-field" filename="jwt-authn.cert" has-file="hasfile.JWTCert"></span>
               <div class="help-text">
                 A certificate containing the public key portion of the key pair used to sign
                 the JSON Web Tokens. This file must be in PEM format.
diff --git a/static/js/core-config-setup.js b/static/js/core-config-setup.js
index e100a01b5..721d7d05d 100644
--- a/static/js/core-config-setup.js
+++ b/static/js/core-config-setup.js
@@ -126,6 +126,7 @@ angular.module("core-config-setup", ['angularFileUpload'])
           '$hasChanges': false
         };
 
+        $scope.hasfile = {};
         $scope.validating = null;
         $scope.savingConfiguration = false;