diff --git a/app/components/Sidebar/Settings.js b/app/components/Sidebar/Settings.js
index d9863100e..60af185ad 100644
--- a/app/components/Sidebar/Settings.js
+++ b/app/components/Sidebar/Settings.js
@@ -7,6 +7,7 @@ import {
   CodeIcon,
   UserIcon,
   LinkIcon,
+  TeamIcon,
 } from 'outline-icons';
 
 import Flex from 'shared/components/Flex';
@@ -55,7 +56,7 @@ class SettingsSidebar extends React.Component<Props> {
             <Section>
               <Header>Team</Header>
               {user.isAdmin && (
-                <SidebarLink to="/settings/details" icon={<SettingsIcon />}>
+                <SidebarLink to="/settings/details" icon={<TeamIcon />}>
                   Details
                 </SidebarLink>
               )}
diff --git a/app/scenes/Settings/components/ImageUpload.js b/app/scenes/Settings/components/ImageUpload.js
index 6c4522719..e0aed52af 100644
--- a/app/scenes/Settings/components/ImageUpload.js
+++ b/app/scenes/Settings/components/ImageUpload.js
@@ -45,7 +45,7 @@ class DropToImport extends React.Component<Props> {
       const asset = await uploadFile(imageBlob, { name: this.file.name });
       this.props.onSuccess(asset.url);
     } catch (err) {
-      this.props.onError(err);
+      this.props.onError(err.message);
     } finally {
       this.isUploading = false;
       this.isCropping = false;
diff --git a/package.json b/package.json
index 40ef2e469..d9e381573 100644
--- a/package.json
+++ b/package.json
@@ -133,7 +133,7 @@
     "nodemailer": "^4.4.0",
     "normalize.css": "^7.0.0",
     "normalizr": "2.0.1",
-    "outline-icons": "^1.1.0",
+    "outline-icons": "^1.2.0",
     "oy-vey": "^0.10.0",
     "pg": "^6.1.5",
     "pg-hstore": "2.3.2",
diff --git a/server/models/Team.js b/server/models/Team.js
index 1ce90d28b..808e85b5b 100644
--- a/server/models/Team.js
+++ b/server/models/Team.js
@@ -1,5 +1,7 @@
 // @flow
+import uuid from 'uuid';
 import { DataTypes, sequelize, Op } from '../sequelize';
+import { publicS3Endpoint, uploadToS3FromUrl } from '../utils/s3';
 import Collection from './Collection';
 import User from './User';
 
@@ -33,6 +35,18 @@ Team.associate = models => {
   Team.hasMany(models.User, { as: 'users' });
 };
 
+const uploadAvatar = async model => {
+  const endpoint = publicS3Endpoint();
+
+  if (model.avatarUrl && !model.avatarUrl.startsWith(endpoint)) {
+    const newUrl = await uploadToS3FromUrl(
+      model.avatarUrl,
+      `avatars/${model.id}/${uuid.v4()}`
+    );
+    if (newUrl) model.avatarUrl = newUrl;
+  }
+};
+
 Team.prototype.createFirstCollection = async function(userId) {
   return await Collection.create({
     name: 'General',
@@ -82,4 +96,6 @@ Team.prototype.activateUser = async function(user: User, admin: User) {
   });
 };
 
+Team.beforeSave(uploadAvatar);
+
 export default Team;
diff --git a/server/models/User.js b/server/models/User.js
index 4c6e68ce9..117b33405 100644
--- a/server/models/User.js
+++ b/server/models/User.js
@@ -4,7 +4,7 @@ import bcrypt from 'bcrypt';
 import uuid from 'uuid';
 import JWT from 'jsonwebtoken';
 import { DataTypes, sequelize, encryptedFields } from '../sequelize';
-import { uploadToS3FromUrl } from '../utils/s3';
+import { publicS3Endpoint, uploadToS3FromUrl } from '../utils/s3';
 import { sendEmail } from '../mailer';
 
 const BCRYPT_COST = process.env.NODE_ENV !== 'production' ? 4 : 12;
@@ -57,9 +57,7 @@ User.associate = models => {
 User.prototype.getJwtToken = function() {
   return JWT.sign({ id: this.id }, this.jwtSecret);
 };
-User.prototype.getTeam = async function() {
-  return this.team;
-};
+
 User.prototype.verifyPassword = function(password) {
   return new Promise((resolve, reject) => {
     if (!this.passwordDigest) {
@@ -77,17 +75,23 @@ User.prototype.verifyPassword = function(password) {
     });
   });
 };
-User.prototype.updateAvatar = async function() {
-  this.avatarUrl = await uploadToS3FromUrl(
-    this.slackData.image_192,
-    `avatars/${this.id}/${uuid.v4()}`
-  );
+
+const uploadAvatar = async model => {
+  const endpoint = publicS3Endpoint();
+
+  if (model.avatarUrl && !model.avatarUrl.startsWith(endpoint)) {
+    const newUrl = await uploadToS3FromUrl(
+      model.avatarUrl,
+      `avatars/${model.id}/${uuid.v4()}`
+    );
+    if (newUrl) model.avatarUrl = newUrl;
+  }
 };
 
 const setRandomJwtSecret = model => {
   model.jwtSecret = crypto.randomBytes(64).toString('hex');
 };
-const hashPassword = function hashPassword(model) {
+const hashPassword = model => {
   if (!model.password) {
     return null;
   }
@@ -106,6 +110,7 @@ const hashPassword = function hashPassword(model) {
 };
 User.beforeCreate(hashPassword);
 User.beforeUpdate(hashPassword);
+User.beforeSave(uploadAvatar);
 User.beforeCreate(setRandomJwtSecret);
 User.afterCreate(user => sendEmail('welcome', user.email));
 
diff --git a/server/utils/s3.js b/server/utils/s3.js
index c8d0c08e1..7edeb384d 100644
--- a/server/utils/s3.js
+++ b/server/utils/s3.js
@@ -68,6 +68,7 @@ export const uploadToS3FromUrl = async (url: string, key: string) => {
         Key: key,
         ContentType: res.headers['content-type'],
         ContentLength: res.headers['content-length'],
+        ServerSideEncryption: 'AES256',
         Body: buffer,
       })
       .promise();
diff --git a/yarn.lock b/yarn.lock
index b7175aba8..cb46e1b43 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -7326,9 +7326,9 @@ outline-icons@^1.0.0:
   version "1.0.3"
   resolved "https://registry.yarnpkg.com/outline-icons/-/outline-icons-1.0.3.tgz#f0928a8bbc7e7ff4ea6762eee8fb2995d477941e"
 
-outline-icons@^1.1.0:
-  version "1.1.0"
-  resolved "https://registry.yarnpkg.com/outline-icons/-/outline-icons-1.1.0.tgz#08eb188a97a1aa8970a4dded7841c3d8b96b8577"
+outline-icons@^1.2.0:
+  version "1.2.0"
+  resolved "https://registry.yarnpkg.com/outline-icons/-/outline-icons-1.2.0.tgz#8a0e0e9e9b98336470228837c4933ba10297fcf5"
 
 oy-vey@^0.10.0:
   version "0.10.0"