diff --git a/app/controllers/profiles_controller.rb b/app/controllers/profiles_controller.rb
index 41bd289d2..453781251 100644
--- a/app/controllers/profiles_controller.rb
+++ b/app/controllers/profiles_controller.rb
@@ -1,13 +1,20 @@
 class ProfilesController < ApplicationController
   before_action :authenticate_user!
+  ALLOWED_USER_PARAMS = %i[email username profile_image].freeze
 
   def update
-    Profiles::Update.call(current_user.profile, update_params)
+    update_result = Profiles::Update.call(current_user, update_params)
+    if update_result.success?
+      flash[:settings_notice] = "Your profile has been updated"
+    else
+      flash[:error] = "Error: #{update_result.error_message}"
+    end
+    redirect_to user_settings_path
   end
 
   private
 
   def update_params
-    params.require(:profile).permit(*Profile.attributes)
+    params.permit(profile: Profile.attributes!, user: ALLOWED_USER_PARAMS)
   end
 end
diff --git a/app/controllers/users_controller.rb b/app/controllers/users_controller.rb
index cc0b8b581..14265ae6c 100644
--- a/app/controllers/users_controller.rb
+++ b/app/controllers/users_controller.rb
@@ -39,11 +39,6 @@ class UsersController < ApplicationController
   def update
     set_current_tab(params["user"]["tab"])
 
-    unless valid_image?
-      render :edit, status: :bad_request
-      return
-    end
-
     if @user.update(permitted_attributes(@user))
       RssReaderFetchUserWorker.perform_async(@user.id) if @user.feed_url.present?
       notice = "Your profile was successfully updated."
@@ -55,7 +50,6 @@ class UsersController < ApplicationController
         ExportContentWorker.perform_async(@user.id)
       end
       cookies.permanent[:user_experience_level] = @user.experience_level.to_s if @user.experience_level.present?
-      follow_hiring_tag(@user)
       flash[:settings_notice] = notice
       @user.touch(:profile_updated_at)
       redirect_to "/settings/#{@tab}"
@@ -234,15 +228,6 @@ class UsersController < ApplicationController
 
   def signout_confirm; end
 
-  def follow_hiring_tag(user)
-    return unless user.looking_for_work?
-
-    hiring_tag = Tag.find_by(name: "hiring")
-    return if !hiring_tag || user.following?(hiring_tag)
-
-    Users::FollowWorker.perform_async(user.id, hiring_tag.id, "Tag")
-  end
-
   def handle_settings_tab
     return @tab = "profile" if @tab.blank?
 
@@ -355,32 +340,6 @@ class UsersController < ApplicationController
     range.cover?(user_identity_age)
   end
 
-  def valid_image?
-    image = params.dig("user", "profile_image")
-    return true unless image
-
-    return true if valid_image_file?(image) && valid_filename?(image)
-
-    Honeycomb.add_field("error", @user.errors.messages)
-    Honeycomb.add_field("errored", true)
-
-    false
-  end
-
-  def valid_image_file?(image)
-    return true if file?(image)
-
-    @user.errors.add(:profile_image, IS_NOT_FILE_MESSAGE)
-    false
-  end
-
-  def valid_filename?(image)
-    return true unless long_filename?(image)
-
-    @user.errors.add(:profile_image, FILENAME_TOO_LONG_MESSAGE)
-    false
-  end
-
   def destroy_request_in_progress?
     Rails.cache.exist?("user-destroy-token-#{@user.id}")
   end
diff --git a/app/models/profile.rb b/app/models/profile.rb
index a881c9c5f..60ef7c8a8 100644
--- a/app/models/profile.rb
+++ b/app/models/profile.rb
@@ -18,6 +18,7 @@ class Profile < ApplicationRecord
     git_lab_url: :gitlab_url,
     linked_in_url: :linkedin_url,
     recruiters_can_contact_me_about_job_opportunities: :contact_consent,
+    skills_languages: :mostly_work_with,
     stack_overflow_url: :stackoverflow_url
   }.with_indifferent_access.freeze
 
diff --git a/app/models/profile_field_group.rb b/app/models/profile_field_group.rb
index c0e02afc5..e54567230 100644
--- a/app/models/profile_field_group.rb
+++ b/app/models/profile_field_group.rb
@@ -6,4 +6,8 @@ class ProfileFieldGroup < ApplicationRecord
   scope :onboarding, lambda {
     includes(:profile_fields).where(profile_fields: { show_in_onboarding: true })
   }
+
+  scope :non_empty_groups, lambda {
+    joins(:profile_fields).includes(:profile_fields).order(:name).uniq
+  }
 end
diff --git a/app/services/profile_fields/add_link_fields.rb b/app/services/profile_fields/add_link_fields.rb
index b290c3c81..75fb0708f 100644
--- a/app/services/profile_fields/add_link_fields.rb
+++ b/app/services/profile_fields/add_link_fields.rb
@@ -8,7 +8,7 @@ module ProfileFields
       field "StackOverflow URL", :text_field, placeholder: "https://stackoverflow.com/users/..."
       field "LinkedIn URL", :text_field, placeholder: "https://www.linkedin.com/in/..."
       field "Behance URL", :text_field, placeholder: "https://www.behance.net/..."
-      field "Dribble URL", :text_field, placeholder: "https://dribble.com/..."
+      field "Dribbble URL", :text_field, placeholder: "https://dribbble.com/..."
       field "Medium URL", :text_field, placeholder: "https://medium.com/@..."
       field "GitLab URL", :text_field, placeholder: "https://gitlab.com/..."
       field "Instagram URL", :text_field, placeholder: "https://www.instagram.com/..."
diff --git a/app/services/profiles/update.rb b/app/services/profiles/update.rb
index 7e1a21757..65a30d989 100644
--- a/app/services/profiles/update.rb
+++ b/app/services/profiles/update.rb
@@ -1,36 +1,29 @@
 module Profiles
   class Update
-    def self.call(profile, updated_attributes = {})
-      new(profile, updated_attributes).call
+    include ImageUploads
+
+    def self.call(user, updated_attributes = {})
+      new(user, updated_attributes).call
     end
 
-    attr_reader
+    attr_reader :error_message
 
-    def initialize(profile, updated_attributes)
-      @profile = profile
-      @updated_attributes = updated_attributes
+    def initialize(user, updated_attributes)
+      @user = user
+      @profile = user.profile
+      @updated_profile_attributes = updated_attributes[:profile] || {}
+      @updated_user_attributes = updated_attributes[:user].to_h || {}
       @success = false
     end
 
     def call
-      # Ensure we have up to date attributes
-      Profile.refresh_attributes!
-
-      # Handle user specific custom profile fields
-      custom_attributes = @updated_attributes.extract!(*@profile.custom_profile_attributes)
-      @updated_attributes[:custom_attributes] = custom_attributes
-
-      # We don't update `data` directly. This uses the defined store_attributes
-      # so we can make use of their typecasting.
-      @profile.assign_attributes(@updated_attributes)
-
-      # Before saving, filter out obsolete profile fields
-      @profile.data.slice!(*Profile.attributes)
-
-      return unless @profile.save
-
-      # Propagate changes back to the `users` table
-      sync_to_user
+      if verify_profile_image && update_profile && sync_to_user
+        @user.touch(:profile_updated_at)
+        follow_hiring_tag
+      else
+        Honeycomb.add_field("error", @error_message)
+        Honeycomb.add_field("errored", true)
+      end
       self
     end
 
@@ -40,13 +33,81 @@ module Profiles
 
     private
 
+    def verify_profile_image
+      image = @updated_user_attributes[:profile_image]
+      return true unless image
+      return true if valid_image_file?(image) && valid_filename?(image)
+
+      false
+    end
+
+    def valid_image_file?(image)
+      return true if file?(image)
+
+      @error_message = IS_NOT_FILE_MESSAGE
+      false
+    end
+
+    def valid_filename?(image)
+      return true unless long_filename?(image)
+
+      @error_message = FILENAME_TOO_LONG_MESSAGE
+      false
+    end
+
+    def update_profile
+      # Ensure we have up to date attributes
+      Profile.refresh_attributes!
+
+      # Handle user specific custom profile fields
+      if (custom_profile_attributes = @profile.custom_profile_attributes).any?
+        custom_attributes = @updated_profile_attributes.extract!(*custom_profile_attributes)
+        @updated_profile_attributes[:custom_attributes] = custom_attributes
+      end
+
+      # We don't update `data` directly. This uses the defined store_attributes
+      # so we can make use of their typecasting.
+      @profile.assign_attributes(@updated_profile_attributes)
+
+      # Before saving, filter out obsolete profile fields
+      @profile.data.slice!(*Profile.attributes)
+
+      @profile.save
+    end
+
+    # Propagate changes back to the `users` table
     def sync_to_user
-      user_attributes = @profile.data.transform_keys do |key|
+      # These are the profile attributes that still exist as columns on User.
+      profile_attributes = @profile.data.transform_keys do |key|
         Profile::MAPPED_ATTRIBUTES.fetch(key, key).to_s
       end
       @profile.user._skip_profile_sync = true
-      @success = true if @profile.user.update(user_attributes.except("custom_attributes"))
+      if @profile.user.update(profile_attributes.except("custom_attributes"))
+        update_user_attributes
+      else
+        @error_message = @user.errors_as_sentence
+      end
+
+      @success
+    ensure
       @profile.user._skip_profile_sync = false
     end
+
+    def update_user_attributes
+      if @user.update(@updated_user_attributes)
+        @success = true
+      else
+        @error_message = @user.errors_as_sentence
+      end
+    end
+
+    def follow_hiring_tag
+      return unless SiteConfig.dev_to? && @user.looking_for_work?
+
+      hiring_tag = Tag.find_by(name: "hiring")
+      return unless hiring_tag && @user.following?(hiring_tag)
+
+      Users::FollowWorker.perform_async(@user.id, hiring_tag.id, "Tag")
+    end
   end
 end
diff --git a/app/views/users/_profile.html.erb b/app/views/users/_profile.html.erb
index 374fe94ff..4cfe2c1f3 100644
--- a/app/views/users/_profile.html.erb
+++ b/app/views/users/_profile.html.erb
@@ -15,26 +15,18 @@
   </div>
 <% end %>
 
-<%= form_for @user, html: { class: "sticky-footer-form" } do |f| %>
+<%= form_with(url: profile_path(@user.profile_id), method: "put", html: { class: "sticky-footer-form" }) do |f| %>
+
   <div class="crayons-card mb-6 grid grid-flow-row gap-6 p-6">
+    <h2>User</h2>
     <div class="crayons-field">
       <%= f.label :email, class: "crayons-field__label" %>
-      <%= f.text_field :email, class: "crayons-textfield", placeholder: "john.doe@example.com" %>
-    </div>
-
-    <div class="crayons-field crayons-field--checkbox">
-      <%= f.check_box :email_public, class: "crayons-checkbox" %>
-      <%= f.label :email_public, "Display email on profile", class: "crayons-field__label" %>
+      <%= f.text_field "user[email]", class: "crayons-textfield", placeholder: "john.doe@example.com", value: @user.email %>
     </div>
 
     <div class="crayons-field">
       <%= f.label :username, class: "crayons-field__label" %>
-      <%= f.text_field :username, maxlength: 30, class: "crayons-textfield", placeholder: "johndoe" %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :name, class: "crayons-field__label" %>
-      <%= f.text_field :name, maxlength: 100, class: "crayons-textfield", placeholder: "John Doe" %>
+      <%= f.text_field "user[username]", maxlength: 30, class: "crayons-textfield", placeholder: "johndoe", value: @user.username %>
     </div>
 
     <div class="crayons-field">
@@ -43,158 +35,32 @@
       <div class="flex items-center">
         <% if @user.profile_image_url.present? %>
           <span class="crayons-avatar crayons-avatar--xl mr-2"><img alt="<%= @user.username %> profile image" src="<%= Images::Profile.call(@user.profile_image_url, length: 50) %>" class="crayons-avatar__image" /></span>
-          <%= f.file_field :profile_image, accept: "image/*", class: "crayons-card crayons-card--secondary p-3 flex items-center flex-1 w-100" %>
+          <%= f.file_field "user[profile_image]", accept: "image/*", class: "crayons-card crayons-card--secondary p-3 flex items-center flex-1 w-100" %>
         <% end %>
       </div>
     </div>
-
-    <div class="crayons-field">
-      <%= f.label :website_url, class: "crayons-field__label" %>
-      <%= f.text_field :website_url, maxlength: 100, class: "crayons-textfield", placeholder: "https://yoursite.com" %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :summary, class: "crayons-field__label" %>
-      <%= f.text_area :summary, maxlength: 200, class: "crayons-textfield", placeholder: "A short bio...", rows: 3 %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :location, class: "crayons-field__label" %>
-      <%= f.text_field :location, maxlength: 100, class: "crayons-textfield", placeholder: "Halifax, Nova Scotia" %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :education, class: "crayons-field__label" %>
-      <%= f.text_field :education, maxlength: 100, class: "crayons-textfield" %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :employer_name, class: "crayons-field__label" %>
-      <%= f.text_field :employer_name, maxlength: 100, class: "crayons-textfield", placeholder: "Acme Inc." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :employer_url, class: "crayons-field__label" %>
-      <%= f.text_field :employer_url, maxlength: 100, class: "crayons-textfield", placeholder: "https://dev.com" %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :employment_title, class: "crayons-field__label" %>
-      <%= f.text_field :employment_title, maxlength: 100, class: "crayons-textfield", placeholder: "Junior Frontend Engineer" %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :mostly_work_with, "Skills/Languages", class: "crayons-field__label" %>
-      <%= f.text_area :mostly_work_with, maxlength: 500, class: "crayons-textfield", rows: 5 %>
-      <p class="crayons-field__description">What tools and languages are you most experienced with? Are you specialized or more of a generalist?</p>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :currently_learning, "I'm getting into", class: "crayons-field__label" %>
-      <%= f.text_area :currently_learning, maxlength: 500, class: "crayons-textfield", rows: 5 %>
-      <p class="crayons-field__description">What are you learning right now? What are the new tools and languages you're picking up in <%= Time.zone.now.year %>?</p>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :currently_hacking_on, "My projects and hacks", class: "crayons-field__label" %>
-      <%= f.text_area :currently_hacking_on, maxlength: 500, class: "crayons-textfield", rows: 5 %>
-      <p class="crayons-field__description">What projects are currently occupying most of your time?</p>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :available_for, class: "crayons-field__label" %>
-      <%= f.text_area :available_for, maxlength: 500, class: "crayons-textfield", rows: 5 %>
-      <p class="crayons-field__description">What kinds of collaborations or discussions are you available for? What's a good reason to say <em>Hey!</em> to you these days?</p>
-    </div>
   </div>
 
-  <div class="crayons-card mb-6 grid gap-4 p-6">
-    <h2>Branding</h2>
-    <%= render partial: "shared/logo_design", locals: { f: f, account: @user } %>
+  <% ProfileFieldGroup.non_empty_groups.each do |group| %>
+    <div class="crayons-card mb-6 grid grid-flow-row gap-6 p-6">
+      <h2><%= group.name %></h2>
+      <% if group.description.present? %>
+        <div class="color-base-40"><%= group.description %></div>
+      <% end %>
+      <% group.profile_fields.each do |field| %>
+        <div class="crayons-field <%= "crayons-field--check_box" if field.input_type == "check_box" %>">
+          <div><%= field.label %></div>
+          <% if field["input_type"] == "check_box" %>
+            <%= f.public_send(field["input_type"], "profile[#{field.attribute_name}]", checked: @user.profile.data[field.attribute_name]) %>
+          <% else %>
+            <%= f.public_send(field["input_type"], "profile[#{field.attribute_name}]", value: @user.profile.data[field.attribute_name]) %>
+          <% end %>
+        </div>
+      <% end %>
+    </div>
+  <% end %>
+
+  <div class="save-footer crayons-card mb-6 grid p-6">
+    <button type="submit" class="crayons-btn">Save Profile Information</button>
   </div>
-
-  <div class="crayons-card mb-6 grid gap-4 p-6">
-    <h2>Work opportunities settings</h2>
-    <div class="crayons-field crayons-field--checkbox">
-      <%= f.check_box :looking_for_work, class: "crayons-checkbox" %>
-      <%= f.label :looking_for_work, class: "crayons-field__label" %>
-    </div>
-
-    <div class="crayons-field crayons-field--checkbox">
-      <%= f.check_box :looking_for_work_publicly, class: "crayons-checkbox" %>
-      <%= f.label :looking_for_work_publicly, "Display \"looking for work\" on profile", class: "crayons-field__label" %>
-    </div>
-
-    <div class="crayons-field crayons-field--checkbox">
-      <%= f.check_box :contact_consent, class: "crayons-checkbox" %>
-      <%= f.label :contact_consent, "Recruiters can contact me about job opportunities", class: "crayons-field__label" %>
-    </div>
-  </div>
-
-  <div class="crayons-card mb-6 grid gap-6 p-6">
-    <h2>Links</h2>
-
-    <div class="crayons-field">
-      <%= f.label :facebook_url, "Facebook profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :facebook_url, class: "crayons-textfield", placeholder: "https://facebook.com/..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :youtube_url, "Youtube URL", class: "crayons-field__label" %>
-      <%= f.url_field :youtube_url, class: "crayons-textfield", placeholder: "https://www.youtube.com/channel/..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :stackoverflow_url, "Stack Overflow profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :stackoverflow_url, class: "crayons-textfield", placeholder: "https://stackoverflow.com/users/..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :linkedin_url, "LinkedIn profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :linkedin_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :behance_url, "Behance profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :behance_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :dribbble_url, "Dribbble profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :dribbble_url, class: "crayons-textfield", placeholder: "https://dribbble.com/..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :medium_url, "Medium profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :medium_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :gitlab_url, "GitLab profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :gitlab_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :instagram_url, "Instagram profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :instagram_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :mastodon_url, "Mastodon profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :mastodon_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-
-    <div class="crayons-field">
-      <%= f.label :twitch_url, "Twitch profile URL", class: "crayons-field__label" %>
-      <%= f.url_field :twitch_url, class: "crayons-textfield", placeholder: "https://..." %>
-    </div>
-  </div>
-
-  <div class="save-footer crayons-card mb-6 grid gap-6 p-6">
-    <%= f.hidden_field :tab, value: @tab %>
-    <div>
-      <button type="submit" class="crayons-btn">Save</button>
-    </div>
-  </div>
-
 <% end %>
diff --git a/lib/data/dev_profile_fields.csv b/lib/data/dev_profile_fields.csv
index ed05e45d9..6962c6221 100644
--- a/lib/data/dev_profile_fields.csv
+++ b/lib/data/dev_profile_fields.csv
@@ -8,7 +8,7 @@ Youtube URL,text_field,https://www.youtube.com/channel/...,,Links
 StackOverflow URL,text_field,https://stackoverflow.com/users/...,,Links
 LinkedIn URL,text_field,https://www.linkedin.com/in/...,,Links
 Behance URL,text_field,https://www.behance.net/...,,Links
-Dribble URL,text_field,https://dribble.com/...,,Links
+Dribbble URL,text_field,https://dribbble.com/...,,Links
 Medium URL,text_field,https://medium.com/@...,,Links
 GitLab URL,text_field,https://gitlab.com/...,,Links
 Instagram URL,text_field,https://www.instagram.com/...,,Links
diff --git a/lib/data_update_scripts/20200922065307_fix_dribbble_url_profile_field.rb b/lib/data_update_scripts/20200922065307_fix_dribbble_url_profile_field.rb
new file mode 100644
index 000000000..557d211ae
--- /dev/null
+++ b/lib/data_update_scripts/20200922065307_fix_dribbble_url_profile_field.rb
@@ -0,0 +1,18 @@
+module DataUpdateScripts
+  class FixDribbbleUrlProfileField
+    def run
+      old_field = ProfileField.find_by(attribute_name: "dribble_url")
+      return unless old_field
+
+      old_field.update(label: "Dribbble URL",
+                       attribute_name: "dribbble_url",
+                       placeholder_text: "https://dribbble.com/...")
+
+      Profile.refresh_attributes!
+
+      User.where.not(dribbble_url: [nil, ""]).find_each do |user|
+        user.profile.update(dribbble_url: user.dribbble_url)
+      end
+    end
+  end
+end
diff --git a/lib/data_update_scripts/20200922072907_backfill_profile_skills_languages.rb b/lib/data_update_scripts/20200922072907_backfill_profile_skills_languages.rb
new file mode 100644
index 000000000..ceb5aa634
--- /dev/null
+++ b/lib/data_update_scripts/20200922072907_backfill_profile_skills_languages.rb
@@ -0,0 +1,9 @@
+module DataUpdateScripts
+  class BackfillProfileSkillsLanguages
+    def run
+      User.where.not(mostly_work_with: [nil, ""]).find_each do |user|
+        user.profile.update(skills_languages: user.mostly_work_with)
+      end
+    end
+  end
+end
diff --git a/spec/requests/user/user_settings_spec.rb b/spec/requests/user/user_settings_spec.rb
index 08bdaea65..d210d889a 100644
--- a/spec/requests/user/user_settings_spec.rb
+++ b/spec/requests/user/user_settings_spec.rb
@@ -199,28 +199,6 @@ RSpec.describe "UserSettings", type: :request do
       expect(response.body).to include("Username is too short")
     end
 
-    it "returns error if Profile image is too large" do
-      profile_image = fixture_file_upload("files/large_profile_img.jpg", "image/jpeg")
-      put "/users/#{user.id}", params: { user: { tab: "profile", profile_image: profile_image } }
-      expect(response.body).to include("Profile image File size should be less than 2 MB")
-    end
-
-    it "returns error if Profile image file name is too long" do
-      profile_image = fixture_file_upload("files/800x600.png", "image/png")
-      allow(profile_image).to receive(:original_filename).and_return("#{'a_very_long_filename' * 15}.png")
-
-      put "/users/#{user.id}", params: { user: { tab: "profile", profile_image: profile_image } }
-
-      expect(response).to have_http_status(:bad_request)
-    end
-
-    it "returns error if Profile image is not a file" do
-      profile_image = "A String"
-      put "/users/#{user.id}", params: { user: { tab: "profile", profile_image: profile_image } }
-
-      expect(response).to have_http_status(:bad_request)
-    end
-
     it "returns error message if user can't be saved" do
       put "/users/#{user.id}", params: { user: { password: "1", password_confirmation: "1" } }
 
diff --git a/spec/services/profiles/update_spec.rb b/spec/services/profiles/update_spec.rb
index e8d00df53..a5002920d 100644
--- a/spec/services/profiles/update_spec.rb
+++ b/spec/services/profiles/update_spec.rb
@@ -4,6 +4,7 @@ RSpec.describe Profiles::Update, type: :service do
   let(:profile) do
     create(:profile, data: { name: "Sloan Doe", looking_for_work: true, removed: "Bla" })
   end
+  let(:user) { profile.user }
 
   before do
     create(:profile_field, label: "Name", input_type: :text_field)
@@ -11,21 +12,29 @@ RSpec.describe Profiles::Update, type: :service do
     Profile.refresh_attributes!
   end
 
+  it "only tries to sync changes to User if the profile update succeeds" do
+    service = described_class.new(user, profile: {}, user: {})
+    allow(service).to receive(:update_profile).and_return(false)
+
+    expect(service).not_to receive(:sync_to_user) # rubocop:disable RSpec/MessageSpies
+    service.call
+  end
+
   it "correctly typecasts new attributes", :aggregate_failures do
-    described_class.call(profile, name: 123, looking_for_work: "false")
+    described_class.call(user, profile: { name: 123, looking_for_work: "false" })
     expect(profile.name).to eq "123"
     expect(profile.looking_for_work).to be false
   end
 
   it "removes old attributes from the profile" do
     expect do
-      described_class.call(profile, {})
+      described_class.call(user, profile: {})
     end.to change { profile.data.key?("removed") }.to(false)
   end
 
   it "propagates changes to user", :agregate_failures do
     new_name = "Sloan Doe"
-    described_class.call(profile, name: new_name)
+    described_class.call(user, profile: {}, user: { name: new_name })
     expect(profile.name).to eq new_name
     expect(profile.user[:name]).to eq new_name
   end
@@ -34,8 +43,38 @@ RSpec.describe Profiles::Update, type: :service do
     custom_profile_field = create(:custom_profile_field, profile: profile)
     custom_attribute = custom_profile_field.attribute_name
 
-    described_class.call(profile, custom_attribute => "Test")
-
+    described_class.call(user, profile: { custom_attribute => "Test" }, user: {})
     expect(profile.custom_attributes[custom_attribute]).to eq "Test"
   end
+
+  it "updates the profile_updated_at column" do
+    expect do
+      described_class.call(user, profile: { name: 123, looking_for_work: "false" })
+    end.to change { user.reload.profile_updated_at }
+  end
+
+  it "returns an error if Profile image is too large" do
+    profile_image = fixture_file_upload("files/large_profile_img.jpg", "image/jpeg")
+    service = described_class.call(user, profile: {}, user: { profile_image: profile_image })
+
+    expect(service.success?).to be false
+    expect(service.error_message).to eq "Profile image File size should be less than 2 MB"
+  end
+
+  it "returns an error if Profile image is not a file" do
+    profile_image = "A String"
+    service = described_class.call(user, profile: {}, user: { profile_image: profile_image })
+
+    expect(service.success?).to be false
+    expect(service.error_message).to eq "invalid file type. Please upload a valid image."
+  end
+
+  it "returns an error if Profile image file name is too long" do
+    profile_image = fixture_file_upload("files/800x600.png", "image/png")
+    allow(profile_image).to receive(:original_filename).and_return("#{'a_very_long_filename' * 15}.png")
+    service = described_class.call(user, profile: {}, user: { profile_image: profile_image })
+
+    expect(service.success?).to be false
+    expect(service.error_message).to eq "filename too long - the max is 250 characters."
+  end
 end
diff --git a/spec/system/user/user_edits_profile_spec.rb b/spec/system/user/user_edits_profile_spec.rb
index 5e6f4de87..3cae26770 100644
--- a/spec/system/user/user_edits_profile_spec.rb
+++ b/spec/system/user/user_edits_profile_spec.rb
@@ -19,9 +19,9 @@ RSpec.describe "User edits their profile", type: :system do
     it "makes the 'Save Button' footer sticky once a field is filled in", js: true do
       expect(page).not_to have_css(".sticky")
 
-      fill_in "user[website_url]", with: "example.com"
+      fill_in "user[username]", with: "sloan"
 
-      find("#user_website_url").native.send_keys :tab # this un-focuses the filled-in field
+      find_field(id: "user[username]").native.send_keys :tab # this un-focuses the filled-in field
 
       expect(page).to have_css(".sticky")
     end
diff --git a/spec/system/user_selects_looking_for_work_spec.rb b/spec/system/user_selects_looking_for_work_spec.rb
index f30cfb877..d9d2e7120 100644
--- a/spec/system/user_selects_looking_for_work_spec.rb
+++ b/spec/system/user_selects_looking_for_work_spec.rb
@@ -4,17 +4,20 @@ RSpec.describe "Looking For Work", type: :system do
   let(:user) { create(:user) }
 
   before do
-    create(:tag, name: "hiring")
-    sign_in(user)
-    visit "/settings"
+    user.follow(create(:tag, name: "hiring"))
+    create(:profile_field, label: "Looking for work", input_type: :check_box)
+    Profile.refresh_attributes!
   end
 
   it "user selects looking for work and autofollows hiring tag", js: true do
-    page.check "Looking for work"
-    sidekiq_perform_enqueued_jobs do
-      click_button("Save")
-    end
-    expect(page).to have_text("Your profile was successfully updated")
+    allow(SiteConfig).to receive(:dev_to?).and_return(true)
+
+    sign_in(user)
+    visit "/settings"
+    page.check("profile[looking_for_work]")
+    sidekiq_perform_enqueued_jobs { click_button("Save") }
+
+    expect(page).to have_text("Your profile has been updated")
     expect(user.follows.count).to eq(1)
   end
 end