diff --git a/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.hbs b/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.hbs
index 88aa13d801f..de3591c9827 100644
--- a/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.hbs
+++ b/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.hbs
@@ -1,6 +1,9 @@
 <label
-  class="wizard-container__button wizard-container__button-upload
-    {{if this.uploading 'disabled'}}"
+  class={{concatClass
+    "wizard-container__button wizard-container__button-upload"
+    (if this.uploading "disabled")
+    (if this.hasUpload "has-upload")
+  }}
 >
   {{#if this.uploading}}
     {{i18n "wizard.uploading"}}
diff --git a/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.js b/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.js
index 87a8162acf7..bdf8d803820 100644
--- a/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.js
+++ b/app/assets/javascripts/discourse/app/static/wizard/components/fields/image.js
@@ -27,6 +27,14 @@ export default class Image extends Component {
     this.setupUploads();
   }
 
+  @discourseComputed("uploading", "field.value")
+  hasUpload() {
+    return (
+      !this.uploading &&
+      !this.field.value.includes("discourse-logo-sketch-small.png")
+    );
+  }
+
   setupUploads() {
     const id = this.field.id;
     this._uppyInstance = new Uppy({
diff --git a/spec/system/page_objects/pages/wizard.rb b/spec/system/page_objects/pages/wizard.rb
index c97db0853cb..0cf4b0291b2 100644
--- a/spec/system/page_objects/pages/wizard.rb
+++ b/spec/system/page_objects/pages/wizard.rb
@@ -46,6 +46,10 @@ module PageObjects
       def fill_field(field_type, field_id, value)
         find_field(field_type, field_id).fill_in(with: value)
       end
+
+      def has_field_with_value?(field_type, field_id, value)
+        find_field(field_type, field_id).find("input").value == value
+      end
     end
   end
 end
@@ -79,6 +83,13 @@ class PageObjects::Pages::Wizard::ReadyStep < PageObjects::Pages::Wizard::StepBa
 end
 
 class PageObjects::Pages::Wizard::BrandingStep < PageObjects::Pages::Wizard::StepBase
+  def click_upload_button(field_id)
+    wizard.find_field("image", field_id).find(".wizard-container__button-upload").click
+  end
+
+  def has_upload?(field_id)
+    wizard.find_field("image", field_id).has_css?(".wizard-container__button-upload.has-upload")
+  end
 end
 
 class PageObjects::Pages::Wizard::StylingStep < PageObjects::Pages::Wizard::StepBase
diff --git a/spec/system/wizard_spec.rb b/spec/system/wizard_spec.rb
index 6d14166eede..d8f1fa6fdc2 100644
--- a/spec/system/wizard_spec.rb
+++ b/spec/system/wizard_spec.rb
@@ -56,9 +56,23 @@ describe "Wizard", type: :system do
   end
 
   describe "Wizard Step: Branding" do
-    it "lets user configure logos and other branding" do
+    let(:file_path_1) { file_from_fixtures("logo.png", "images").path }
+    let(:file_path_2) { file_from_fixtures("logo.jpg", "images").path }
+
+    it "lets user configure logos" do
       wizard_page.go_to_step("branding")
       expect(wizard_page).to be_on_step("branding")
+      attach_file(file_path_1) { wizard_page.branding_step.click_upload_button("logo") }
+      expect(wizard_page.branding_step).to have_upload("logo")
+      attach_file(file_path_2) { wizard_page.branding_step.click_upload_button("logo-small") }
+      expect(wizard_page.branding_step).to have_upload("logo-small")
+      wizard_page.go_to_next_step
+      expect(wizard_page).to be_on_step("corporate")
+
+      expect(SiteSetting.logo).to eq(Upload.find_by(original_filename: File.basename(file_path_1)))
+      expect(SiteSetting.logo_small).to eq(
+        Upload.find_by(original_filename: File.basename(file_path_2)),
+      )
     end
   end
 
@@ -115,6 +129,26 @@ describe "Wizard", type: :system do
     it "lets user configure corporate including governing law and city for disputes" do
       wizard_page.go_to_step("corporate")
       expect(wizard_page).to be_on_step("corporate")
+      wizard_page.fill_field("text", "company-name", "ACME")
+      wizard_page.fill_field("text", "governing-law", "California")
+      wizard_page.fill_field("text", "contact-url", "https://ac.me")
+      wizard_page.fill_field("text", "city-for-disputes", "San Francisco")
+      wizard_page.fill_field("text", "contact-email", "coyote@ac.me")
+      wizard_page.click_jump_in
+      expect(page).to have_current_path("/latest")
+
+      expect(SiteSetting.company_name).to eq("ACME")
+      expect(SiteSetting.governing_law).to eq("California")
+      expect(SiteSetting.city_for_disputes).to eq("San Francisco")
+      expect(SiteSetting.contact_url).to eq("https://ac.me")
+      expect(SiteSetting.contact_email).to eq("coyote@ac.me")
+
+      wizard_page.go_to_step("corporate")
+      expect(wizard_page).to have_field_with_value("text", "company-name", "ACME")
+      expect(wizard_page).to have_field_with_value("text", "governing-law", "California")
+      expect(wizard_page).to have_field_with_value("text", "contact-url", "https://ac.me")
+      expect(wizard_page).to have_field_with_value("text", "city-for-disputes", "San Francisco")
+      expect(wizard_page).to have_field_with_value("text", "contact-email", "coyote@ac.me")
     end
   end
 end