diff --git a/app/controllers/admin/memberships_controller.rb b/app/controllers/admin/memberships_controller.rb
index 0ad4daf0..7d9eb8d0 100644
--- a/app/controllers/admin/memberships_controller.rb
+++ b/app/controllers/admin/memberships_controller.rb
@@ -60,9 +60,29 @@ def unmake_admin
     redirect_to admin_memberships_path
   end
 
+  # updating scholarship status
+  #if requested --> approve (approve=true), revoke (approve=false)
+  #if approved --> revoke (approve=true), continue (approve=true)
+  #if not-requested --> approve
+  def approve_or_continue_scholarship
+    user = User.find(params[:id])
+    if user.scholarship_since?
+      user.scholarship_continued
+    else
+      user.scholarship_approved
+    end
+    redirect_to admin_memberships_path
+  end
+
+  def remove_scholarship
+    user = User.find(params[:id])
+    user.scholarship_rejected_or_revoked
+    redirect_to admin_memberships_path
+  end
+
   private
 
   def user_params
-    params.require(:user).permit(:is_scholarship)
+    params.require(:user)
   end
 end
diff --git a/app/controllers/members/dues_controller.rb b/app/controllers/members/dues_controller.rb
index e649bf8d..2ab9baec 100644
--- a/app/controllers/members/dues_controller.rb
+++ b/app/controllers/members/dues_controller.rb
@@ -61,6 +61,7 @@ def update
   end
 
   def scholarship_request
+    current_user.request_scholarship
     DuesMailer.scholarship_requested(current_user, params[:reason]).deliver_now
 
     redirect_to members_user_dues_path, notice: "Your scholarship request has been submitted"
diff --git a/app/models/concerns/admin_user.rb b/app/models/concerns/admin_user.rb
index 1d7a7540..fbfd4907 100644
--- a/app/models/concerns/admin_user.rb
+++ b/app/models/concerns/admin_user.rb
@@ -14,4 +14,18 @@ def unmake_admin!
     self.is_admin = false
     save!
   end
+
+  def scholarship_approved
+    update_attributes!({scholarship_since: DateTime.now, scholarship_last_checkin: DateTime.now})
+  end
+
+  def scholarship_rejected_or_revoked
+    update_attributes!({requested_scholarship: nil, scholarship_since: nil, scholarship_last_checkin: nil})
+  end
+
+  def scholarship_continued
+    return unless scholarship_since?
+
+    touch :scholarship_last_checkin
+  end
 end
diff --git a/app/models/user.rb b/app/models/user.rb
index b87c695c..91c5173b 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -4,7 +4,9 @@ class User < ApplicationRecord
   EMAIL_PATTERN = /\A.+@.+\Z/
 
   attr_accessible :username, :name, :email, :profile_attributes, :pronounceable_name,
-    :application_attributes, :email_for_google, :dues_pledge, :is_scholarship, :voting_policy_agreement
+    :application_attributes, :email_for_google, :dues_pledge,
+    :requested_scholarship, :scholarship_since, :scholarship_last_checkin,
+    :voting_policy_agreement
 
   validates :state, presence: true
 
@@ -164,6 +166,10 @@ def update_stripe_record
     )
   end
 
+  def request_scholarship
+    touch :requested_scholarship
+  end
+
   def display_state
     state.tr("_", " ")
   end
@@ -219,12 +225,14 @@ def gravatar_email
 #  email                        :string
 #  email_for_google             :string
 #  is_admin                     :boolean          default(FALSE)
-#  is_scholarship               :boolean          default(FALSE)
 #  last_logged_in_at            :datetime
 #  last_stripe_charge_succeeded :datetime
 #  membership_note              :text
 #  name                         :string
 #  pronounceable_name           :string
+#  requested_scholarship        :datetime
+#  scholarship_last_checkin     :datetime
+#  scholarship_since            :datetime
 #  setup_complete               :boolean
 #  state                        :string           not null
 #  username                     :string
diff --git a/app/service_objects/account_setup_reminder.rb b/app/service_objects/account_setup_reminder.rb
index cb6fb33e..ba892e2e 100644
--- a/app/service_objects/account_setup_reminder.rb
+++ b/app/service_objects/account_setup_reminder.rb
@@ -8,6 +8,9 @@ def send_emails
       processed_at = user.application.processed_at
       next unless processed_at
 
+      # if member requested a scholarship and it hasn't been approved yet, then don't send emails
+      next if user.requested_scholarship.present? and not user.scholarship_since.present?
+
       if processed_at < 2.days.ago && processed_at > 4.days.ago
         NewMembersMailer.three_day_reminder(user).deliver_now
       elsif processed_at < 6.days.ago && processed_at > 8.days.ago
diff --git a/app/views/admin/_new_member.html.haml b/app/views/admin/_new_member.html.haml
index de93a727..9b0d3d90 100644
--- a/app/views/admin/_new_member.html.haml
+++ b/app/views/admin/_new_member.html.haml
@@ -12,7 +12,7 @@
   .col-md-4
     %ul.list-unstyled
       %li
-        %b Approved on #{ new_member.application.processed_at.strftime("%b %-d") }
+        %b Approved on #{ new_member.application.processed_at? ? new_member.application.processed_at.strftime("%b %-d") : '---' }
       %li
         - if new_member.email_for_google
           %b Google email:
@@ -21,12 +21,11 @@
           .admin-warning
             No Google email
       %li
-        - if new_member.last_stripe_charge_succeeded
-          %b Stripe Payment Made On:
-          = new_member.last_stripe_charge_succeeded
+        - if new_member.last_stripe_charge_succeeded or new_member.scholarship_since?
+          Stripe charge succeeded OR Scholarship approved
         - else
           .admin-warning
-            Dues Not Set Up
+            Dues Not Set Up or Waiting on Scholarship
   .col-md-4
     = form_for :user, url: admin_save_membership_note_path do |f|
       = f.hidden_field :id, value: new_member.id
diff --git a/app/views/admin/dues.html.haml b/app/views/admin/dues.html.haml
index 9ab4982c..bc5675f0 100644
--- a/app/views/admin/dues.html.haml
+++ b/app/views/admin/dues.html.haml
@@ -26,6 +26,6 @@
           - if user.name.present?
             = link_to user.name, members_user_path(user)
         %td= user.email
-        %td= user.is_scholarship
+        %td= user.scholarship_since.present?
         %td= user.stripe_customer_id.present? ? "Yes" : "No"
         %td= user.last_stripe_charge_succeeded.strftime('%b %d %Y') if user.last_stripe_charge_succeeded
diff --git a/app/views/admin/memberships/_members.html.haml b/app/views/admin/memberships/_members.html.haml
index a6645991..6dc14eef 100644
--- a/app/views/admin/memberships/_members.html.haml
+++ b/app/views/admin/memberships/_members.html.haml
@@ -28,14 +28,36 @@
             Not set
         %td= user.display_state
         %td
-          = user.is_scholarship ? "Yes" : "No"
-          = form_for user, url: admin_membership_path(user) do |f|
+          -# 'No' if no request or scholarship status.  Button for enabling
+          -# 'Requested/Approved/Checkin' dates if any status.  Buttons for continuing or removing
+          - if not user.requested_scholarship.present? and not user.scholarship_since.present?
+            = "No"
+          - else
+            %table
+              %tr
+                %td
+                  = "Requested:"
+                %td
+                  = "#{user.requested_scholarship.present? ? user.requested_scholarship.try(:strftime, '%Y-%m-%d') : '---'}"
+              %tr
+                %td
+                  = "Approved:"
+                %td
+                  = "#{user.scholarship_since.present? ? user.scholarship_since.try(:strftime, '%Y-%m-%d') : '---'}"
+              %tr
+                %td
+                  = "Last Checkin:"
+                %td
+                  = "#{user.scholarship_last_checkin.try(:strftime, '%Y-%m-%d')}"
+
+          = form_for user, url: admin_approve_or_continue_scholarship_path(user) do |f|
             = f.hidden_field(:id)
-            = f.hidden_field(:is_scholarship, value: !user.is_scholarship)
-            - if user.is_scholarship
+            = f.submit "#{user.scholarship_since.present? ? 'Continue scholarship' : 'Allow scholarship'}", class: "btn", data: { confirm: "Are you sure? Note: This does not change the member's dues in Stripe."}
+
+          - if user.requested_scholarship.present? or user.scholarship_since.present?
+            = form_for user, url: admin_remove_scholarship_path(user) do |f|
+              = f.hidden_field(:id)
               = f.submit "Remove scholarship", class: "btn", data: { confirm: "Are you sure? Note: This does not change the member's dues in Stripe." }
-            - else
-              = f.submit "Mark as on scholarship", class: "btn", data: { confirm: "Are you sure? Note: This does not change the member's dues in Stripe." }
 
         %td= user.last_stripe_charge_succeeded.strftime('%b %d %Y') if user.last_stripe_charge_succeeded
 
diff --git a/app/views/members/dues/show.html.haml b/app/views/members/dues/show.html.haml
index 28a42817..c78eced7 100644
--- a/app/views/members/dues/show.html.haml
+++ b/app/views/members/dues/show.html.haml
@@ -22,7 +22,7 @@
     %b
       #{number_to_currency (@subscription.plan.amount / 100)}
     per #{@subscription.plan.interval}, and your status is <b>#{@subscription.status}</b>.
-- elsif current_user.is_scholarship?
+- elsif current_user.scholarship_since.present?
   %p You are receiving a scholarship for your dues payments.
 - else
   %p You don't have a Stripe subscription yet, or it may have been canceled. Please add your credit or debit card, or request a scholarship below! <3
diff --git a/config/routes.rb b/config/routes.rb
index a6b4fb99..70b1defd 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -34,6 +34,8 @@
     patch "memberships/:id/change_membership_state" => "memberships#change_membership_state", :as => "change_membership_state"
     patch "memberships/:id/make_admin" => "memberships#make_admin", :as => "make_admin"
     patch "memberships/:id/unmake_admin" => "memberships#unmake_admin", :as => "unmake_admin"
+    patch "memberships/:id/approve_or_continue_scholarship" => "memberships#approve_or_continue_scholarship", :as => "approve_or_continue_scholarship"
+    patch "memberships/:id/remove_scholarship" => "memberships#remove_scholarship", :as => "remove_scholarship"
   end
 
   get "admin/new_members" => "admin#new_members"
diff --git a/db/migrate/20221010052254_add_scholarship_since_to_user.rb b/db/migrate/20221010052254_add_scholarship_since_to_user.rb
new file mode 100644
index 00000000..384b4715
--- /dev/null
+++ b/db/migrate/20221010052254_add_scholarship_since_to_user.rb
@@ -0,0 +1,34 @@
+class AddScholarshipSinceToUser < ActiveRecord::Migration[6.0]
+  def change
+    # Currently have a boolean column is_scholarship
+    # Add a column requested_scholarship
+    #     that can be used to show who's requested a scholarship (approved or waiting)
+    # Add a column scholarship_since
+    #     to show date the scholarship was approved
+    # Add a column scholarship_last_checkin
+    #     to show the last check-in and member requested to continue scholarship
+    # For default date values, if is_scholarship is true,
+    #     will set dates to 2022-07-10 (as approximate time of last checkin)
+    # To revert this migration, will have to go back to single boolean column
+    
+    reversible do |dir|
+      dir.up do
+        add_column :users, :requested_scholarship, :timestamp, default: nil
+        add_column :users, :scholarship_since, :timestamp, default: nil
+        add_column :users, :scholarship_last_checkin, :timestamp, default: nil
+
+        execute "UPDATE users SET requested_scholarship = '2022-07-10', scholarship_since = '2022-07-10', scholarship_last_checkin = '2022-07-10' WHERE is_scholarship = true"
+        
+        remove_column :users, :is_scholarship
+      end
+    
+      dir.down do
+        add_column :users, :is_scholarship, :boolean, default: false
+
+        execute "UPDATE users SET is_scholarship = true WHERE scholarship_since IS NOT NULL"
+        
+        remove_columns :users, :requested_scholarship, :scholarship_since, :scholarship_last_checkin
+      end
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index e85f41e8..be86d9dd 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema.define(version: 2022_01_29_183750) do
+ActiveRecord::Schema.define(version: 2022_10_10_052254) do
 
   # These are extensions that must be enabled in order to support this database
   enable_extension "plpgsql"
@@ -112,9 +112,11 @@
     t.text "membership_note"
     t.string "stripe_customer_id"
     t.datetime "last_stripe_charge_succeeded"
-    t.boolean "is_scholarship", default: false
     t.boolean "voting_policy_agreement", default: false
     t.string "pronounceable_name"
+    t.datetime "requested_scholarship"
+    t.datetime "scholarship_since"
+    t.datetime "scholarship_last_checkin"
   end
 
   create_table "votes", id: :serial, force: :cascade do |t|
diff --git a/spec/controllers/admin/memberships_controller_spec.rb b/spec/controllers/admin/memberships_controller_spec.rb
index a5985c30..e4728bf0 100644
--- a/spec/controllers/admin/memberships_controller_spec.rb
+++ b/spec/controllers/admin/memberships_controller_spec.rb
@@ -47,17 +47,51 @@
     end
   end
 
-  describe "PUT update" do
-    subject { put :update, params: params }
+  describe "PATCH approve_scholarship" do
+    subject { patch :approve_or_continue_scholarship, params: params }
+    before { login_as(:member, is_admin: true) }
 
-    before { login_as(:voting_member, is_admin: true) }
-
-    context "marking a member as on scholarship" do
+    context "mark any member not on scholarship as on scholarship" do
       let(:member) { create :member }
-      let(:params) { {id: member.id, user: {is_scholarship: true}} }
+      let(:params) { {id: member.id} }
+
+      it "should set scholarship_since and last_checkin" do
+        expect { subject }.to change { member.reload.scholarship_since }.from(nil).to be_within(1.second).of Time.now
+        expect(member.scholarship_last_checkin).to be_within(1.second).of Time.now
+      end
+    end
+
+    context "mark a scholarship member as continuing scholarship" do
+      let(:member) { create :member, scholarship_since: Time.now }
+      let(:params) { {id: member.id} }
+
+      it "should set scholarship_since and last_checkin" do
+        expect { subject }.not_to change { member.reload.scholarship_since }
+        expect(member.scholarship_last_checkin).to be_within(1.second).of Time.now
+      end
+    end
+  end
+
+  describe "PATCH remove_scholarship" do
+    subject { patch :remove_scholarship, params: params }
+    before { login_as(:member, is_admin: true) }
+
+    context "mark member requesting scholarship as rejected" do
+      let(:member) { create :member, requested_scholarship: Time.now}
+      let(:params) { {id: member.id} }
+
+      it "should remove scholarship request" do
+        expect { subject }.to change { member.reload.requested_scholarship }.to be_nil
+      end
+    end
+
+    context "marking a member as not on scholarship" do
+      let(:member) { create :member, scholarship_since: Time.now}
+      let(:params) { {id: member.id} }
 
-      it "should mark scholarship as true" do
-        expect { subject }.to change { member.reload.is_scholarship }.from(false).to(true)
+      it "should mark scholarship as false" do
+        expect { subject }.to change { member.reload.scholarship_since }.to be_nil
+        expect(member.scholarship_last_checkin).to be_nil
       end
     end
   end
diff --git a/spec/controllers/members/dues_controller_spec.rb b/spec/controllers/members/dues_controller_spec.rb
index 0bfbe47d..ab72c9a9 100644
--- a/spec/controllers/members/dues_controller_spec.rb
+++ b/spec/controllers/members/dues_controller_spec.rb
@@ -216,10 +216,12 @@
     context "logged in as a member" do
       before { login_as member }
 
-      it "sends an email" do
+      it "sends an email and marks as requested scholarship" do
         expect { subject }.to change { ActionMailer::Base.deliveries.count }.by(1)
         expect(ActionMailer::Base.deliveries.last.to).to eq(["scholarship@doubleunion.org", member.email])
         expect(ActionMailer::Base.deliveries.last.body).to include "Lemurs are pretty great"
+        expect(member.reload.requested_scholarship).not_to be_nil
+        expect(member.reload.requested_scholarship).to be_within(1.second).of Time.now
       end
     end
   end
diff --git a/spec/features/update_member_status_spec.rb b/spec/features/update_member_status_spec.rb
index bea658f0..95292e55 100644
--- a/spec/features/update_member_status_spec.rb
+++ b/spec/features/update_member_status_spec.rb
@@ -52,16 +52,28 @@
       it "allows members to be marked as on scholarship" do
         visit admin_memberships_path
         within(".user-#{member.id}") do
-          click_button "Mark as on scholarship"
+          click_button "Allow scholarship"
         end
 
         within(".user-#{member.id}") do
-          expect(page).to have_content "Yes"
+          expect(page).to have_content "Approved"
+          expect(page).to have_content "Last Checkin"
         end
       end
 
       context "with a scholarship member" do
-        before { member.update_attributes(is_scholarship: true) }
+        before { member.update_attributes(scholarship_since: Time.now) }
+
+        it "allows members to be marked as continuing scholarship" do
+          visit admin_memberships_path
+          within(".user-#{member.id}") do
+            click_button "Continue scholarship"
+          end
+
+          within(".user-#{member.id}") do
+            expect(page).to have_content "Last Checkin:"
+          end
+        end
 
         it "allows members to be marked as not on scholarship" do
           visit admin_memberships_path
diff --git a/spec/service_objects/account_setup_reminder_spec.rb b/spec/service_objects/account_setup_reminder_spec.rb
index 9b446983..7bf61b21 100644
--- a/spec/service_objects/account_setup_reminder_spec.rb
+++ b/spec/service_objects/account_setup_reminder_spec.rb
@@ -11,6 +11,8 @@
 
     subject { AccountSetupReminder.new(users).send_emails }
 
+    #Steps for setup complete: google-email, dues, membership coordinator manual steps (access to google docs/drive, mailing list)
+
     context "with no reminders needed" do
       it "sends no emails" do
         subject
@@ -18,6 +20,33 @@
       end
     end
 
+    context "scholarship applicant still waiting for approval after 21 days" do
+      before do
+        member.request_scholarship
+        member.application.update_column(:processed_at, 21.days.ago)
+        other_member.application.update_column(:processed_at, 21.days.ago)
+      end
+
+      it "sends no emails" do
+        subject
+        expect(deliveries.count).to eq 0
+      end
+    end
+
+    context "scholarship applicant got approval within 3 days. But doesn't have setup complete" do
+      let(:member) { create :member, requested_scholarship: Time.now, scholarship_since: Time.now }
+      before do
+        member.application.update_column(:processed_at, 3.days.ago)
+        other_member.application.update_column(:processed_at, 3.days.ago)
+      end
+
+      it "sends a reminder email (maybe they don't have google email setup?)" do
+        subject
+        expect(deliveries.count).to eq 1
+      end
+    end
+
+
     context "with one 3 day reminder" do
       before do
         member.application.update_column(:processed_at, 3.days.ago)