diff --git a/drivers/place/auto_release.cr b/drivers/place/auto_release.cr
index f5060780a11..08219e90237 100644
--- a/drivers/place/auto_release.cr
+++ b/drivers/place/auto_release.cr
@@ -7,13 +7,19 @@ class Place::AutoRelease < PlaceOS::Driver
   generic_name :AutoRelease
   description %(emails visitors to confirm automatic release of their booking when they have indicated they are not on-site and releases the booking if they do not confirm)
 
+  # time_window_hours: The number of hours to check for bookings pending release
+  #
+  # release_locations: Locations to release bookings for
+  # available locations:
+  # - wfh: Work From Home
+  # - aol: Away on Leave
+  # - wfo: Work From Office
   default_settings({
-    timezone:       "GMT",
-    send_emails:    "15 */1 * * *",
-    email_template: "auto_release",
-    # release_url: "https://example.com/release",
-    time_window_hours: 2,
-    release_locations: ["wfh"],
+    timezone:          "GMT",
+    send_emails:       "*/5 * * * *",
+    email_template:    "auto_release",
+    time_window_hours: 4,
+    release_locations: ["wfh", "aol"],
   })
 
   accessor staff_api : StaffAPI_1
@@ -149,45 +155,69 @@ class Place::AutoRelease < PlaceOS::Driver
   end
 
   def release_bookings
-    released_bookings = [] of Booking
-    bookings = Array(Booking).from_json self[:pending_release].to_json
+    released_booking_ids = [] of Int64
+    bookings = self[:pending_release]? ? Array(Booking).from_json(self[:pending_release].to_json) : [] of Booking
+
+    previously_released = self[:released_booking_ids]? ? Array(Int64).from_json(self[:released_booking_ids].to_json) : [] of Int64
+    # remove previously released bookings that are no longer pending release
+    previously_released -= previously_released - bookings.map(&.id)
+    # add previously released bookings that are still pending release
+    released_booking_ids += previously_released
 
     bookings.each do |booking|
-      if @auto_release.time_after > 0 && Time.utc.to_unix - booking.booking_start < @auto_release.time_after / 60
+      next if previously_released.includes? booking.id
+
+      if @auto_release.time_after > 0 && Time.utc.to_unix - booking.booking_start > @auto_release.time_after / 60
         logger.debug { "rejecting booking #{booking.id} as it is within the time_after window" }
         staff_api.reject(booking.id).get
-        released_bookings << booking
+        released_booking_ids << booking.id
       end
     end
 
-    logger.debug { "released #{released_bookings.size} bookings" }
+    logger.debug { "released #{released_booking_ids.size} bookings" }
 
-    released_bookings
+    self[:released_booking_ids] = released_booking_ids
   rescue error
     logger.warn(exception: error) { "unable to release bookings" }
-    [] of Booking
+    self[:released_booking_ids] = [] of Int64
   end
 
   @[Security(Level::Support)]
   def send_release_emails
-    bookings = Array(Booking).from_json self[:pending_release].to_json
+    emailed_booking_ids = [] of Int64
+    bookings = self[:pending_release]? ? Array(Booking).from_json(self[:pending_release].to_json) : [] of Booking
+
+    previously_emailed = self[:emailed_booking_ids]? ? Array(Int64).from_json(self[:emailed_booking_ids].to_json) : [] of Int64
+    # remove previously emailed bookings that are no longer pending release
+    previously_emailed -= previously_emailed - bookings.map(&.id)
+    # add previously emailed bookings that are still pending release
+    emailed_booking_ids += previously_emailed
 
     bookings.each do |booking|
-      begin
-        mailer.send_template(
-          to: booking.user_email,
-          template: {@email_template, "auto_release"},
-          args: {
-            booking_id:    booking.id,
-            user_email:    booking.user_email,
-            user_name:     booking.user_name,
-            booking_start: booking.booking_start,
-            booking_end:   booking.booking_end,
-          })
-      rescue error
-        logger.warn(exception: error) { "failed to send release email to #{booking.user_email}" }
+      next if previously_emailed.includes? booking.id
+
+      if @auto_release.time_before > 0 &&
+         (booking.booking_start - Time.utc.to_unix < @auto_release.time_before / 60) &&
+         (Time.utc.to_unix - booking.booking_start < @auto_release.time_after / 60)
+        logger.debug { "sending release email to #{booking.user_email} for booking #{booking.id} as it is withing the time_before window" }
+        begin
+          mailer.send_template(
+            to: booking.user_email,
+            template: {@email_template, "auto_release"},
+            args: {
+              booking_id:    booking.id,
+              user_email:    booking.user_email,
+              user_name:     booking.user_name,
+              booking_start: booking.booking_start,
+              booking_end:   booking.booking_end,
+            })
+          emailed_booking_ids << booking.id
+        rescue error
+          logger.warn(exception: error) { "failed to send release email to #{booking.user_email}" }
+        end
       end
     end
+    self[:emailed_booking_ids] = emailed_booking_ids
   end
 
   # time_before and time_after are in minutes
diff --git a/drivers/place/auto_release_spec.cr b/drivers/place/auto_release_spec.cr
index ef7ff3bd75c..ff2a4b8cf7c 100644
--- a/drivers/place/auto_release_spec.cr
+++ b/drivers/place/auto_release_spec.cr
@@ -2,6 +2,14 @@ require "placeos-driver/spec"
 require "placeos-driver/interface/mailer"
 
 class StaffAPI < DriverSpecs::MockDriver
+  def on_load
+    self[:rejected] = 0
+  end
+
+  def reject(booking_id : String | Int64, utm_source : String? = nil)
+    self[:rejected] = self[:rejected].as_i + 1
+  end
+
   def query_bookings(
     type : String? = nil,
     period_start : Int64? = nil,
@@ -19,37 +27,129 @@ class StaffAPI < DriverSpecs::MockDriver
     bookings = [
       {
         id:              1,
-        user_id:         "user-wYLBwmC7GFbupt",
+        user_id:         "user-wfh",
         user_email:      "user_one@example.com",
         user_name:       "User One",
         asset_id:        "desk_001",
-        zones:           ["zone_one"],
+        zones:           ["zone-1234"],
         booking_type:    "desk",
         booking_start:   (Time.utc + 1.hour).to_unix,
         booking_end:     (Time.utc + 2.hours).to_unix,
         timezone:        "Australia/Darwin",
-        title:           "Booking",
-        description:     "desk one",
+        title:           "ignore",
+        description:     "",
+        checked_in:      false,
+        rejected:        false,
+        approved:        true,
+        booked_by_id:    "user-wfh",
+        booked_by_email: "user_one@example.com",
+        booked_by_name:  "User One",
+        process_state:   "approved",
+        last_changed:    Time.utc.to_unix,
+        created:         Time.utc.to_unix,
+      },
+      {
+        id:              2,
+        user_id:         "user-wfh",
+        user_email:      "user_one@example.com",
+        user_name:       "User One",
+        asset_id:        "desk_002",
+        zones:           ["zone-1234"],
+        booking_type:    "desk",
+        booking_start:   (Time.utc).to_unix,
+        booking_end:     (Time.utc + 1.hour).to_unix,
+        timezone:        "Australia/Darwin",
+        title:           "notify",
+        description:     "",
         checked_in:      false,
         rejected:        false,
         approved:        true,
-        booked_by_id:    "user-wYLBwmC7GFbupt",
+        booked_by_id:    "user-wfh",
         booked_by_email: "user_one@example.com",
         booked_by_name:  "User One",
         process_state:   "approved",
         last_changed:    Time.utc.to_unix,
         created:         Time.utc.to_unix,
       },
+      {
+        id:              3,
+        user_id:         "user-wfh",
+        user_email:      "user_one@example.com",
+        user_name:       "User One",
+        asset_id:        "desk_003",
+        zones:           ["zone-1234"],
+        booking_type:    "desk",
+        booking_start:   (Time.utc - 11.minutes).to_unix,
+        booking_end:     (Time.utc + 1.hour).to_unix,
+        timezone:        "Australia/Darwin",
+        title:           "reject",
+        description:     "",
+        checked_in:      false,
+        rejected:        false,
+        approved:        true,
+        booked_by_id:    "user-wfh",
+        booked_by_email: "user_one@example.com",
+        booked_by_name:  "User One",
+        process_state:   "approved",
+        last_changed:    Time.utc.to_unix,
+        created:         Time.utc.to_unix,
+      },
+      {
+        id:              4,
+        user_id:         "user-wfh",
+        user_email:      "user_one@example.com",
+        user_name:       "User One",
+        asset_id:        "desk_004",
+        zones:           ["zone-1234"],
+        booking_type:    "desk",
+        booking_start:   (Time.utc + 5.hours).to_unix,
+        booking_end:     (Time.utc + 6.hours).to_unix,
+        timezone:        "Australia/Darwin",
+        title:           "ignore_after_hours",
+        description:     "",
+        checked_in:      false,
+        rejected:        false,
+        approved:        true,
+        booked_by_id:    "user-wfh",
+        booked_by_email: "user_one@example.com",
+        booked_by_name:  "User One",
+        process_state:   "approved",
+        last_changed:    Time.utc.to_unix,
+        created:         Time.utc.to_unix,
+      },
+      {
+        id:              5,
+        user_id:         "user-wfo",
+        user_email:      "user_two@example.com",
+        user_name:       "User Two",
+        asset_id:        "desk_003",
+        zones:           ["zone-1234"],
+        booking_type:    "desk",
+        booking_start:   (Time.utc - 11.minutes).to_unix,
+        booking_end:     (Time.utc + 1.hour).to_unix,
+        timezone:        "Australia/Darwin",
+        title:           "ignore_wfo",
+        description:     "",
+        checked_in:      false,
+        rejected:        false,
+        approved:        true,
+        booked_by_id:    "user-wfo",
+        booked_by_email: "user_two@example.com",
+        booked_by_name:  "User Two",
+        process_state:   "approved",
+        last_changed:    Time.utc.to_unix,
+        created:         Time.utc.to_unix,
+      },
     ]
 
     JSON.parse(bookings.to_json)
   end
 
   def user(id : String)
-    user = {
+    user_wfh = {
       created_at:       Time.utc.to_unix,
       id:               id,
-      email_digest:     "5acf9dfa861dbeabde3dc0a2148a0f2b",
+      email_digest:     "not_real_digest",
       name:             "User One",
       first_name:       "User",
       last_name:        "One",
@@ -57,53 +157,57 @@ class StaffAPI < DriverSpecs::MockDriver
       country:          "Australia",
       building:         "",
       image:            "",
-      authority_id:     "authority-wYLBwmC7GFbupt",
+      authority_id:     "authority-wfh",
       deleted:          false,
       department:       "",
-      work_preferences: [
+      work_preferences: 7.times.map do |i|
         {
-          day_of_week: 0,
-          start_time:  9,
-          end_time:    17,
-          location:    "wfo",
-        },
-        {
-          day_of_week: 1,
-          start_time:  9,
-          end_time:    17,
-          location:    "wfo",
-        },
-        {
-          day_of_week: 2,
-          start_time:  9,
-          end_time:    17,
-          location:    "wfh",
-        },
-        {
-          day_of_week: 3,
-          start_time:  9,
-          end_time:    17,
+          day_of_week: i,
+          start_time:  (Time.utc - 4.hours).hour,
+          end_time:    (Time.utc + 4.hours).hour,
           location:    "wfh",
-        },
-        {
+        }
+      end,
+      work_overrides: {
+        "2024-02-15": {
           day_of_week: 4,
           start_time:  9,
           end_time:    17,
-          location:    "wfh",
-        },
-        {
-          day_of_week: 5,
-          start_time:  9,
-          end_time:    17,
-          location:    "wfh",
+          location:    "wfo",
         },
+      },
+      sys_admin:   false,
+      support:     false,
+      email:       "user_one@example.com",
+      phone:       "",
+      ui_theme:    "light",
+      login_name:  "",
+      staff_id:    "",
+      card_number: "",
+    }
+
+    user_wfo = {
+      created_at:       Time.utc.to_unix,
+      id:               id,
+      email_digest:     "not_real_digest",
+      name:             "User Two",
+      first_name:       "User",
+      last_name:        "Two",
+      groups:           [] of String,
+      country:          "Australia",
+      building:         "",
+      image:            "",
+      authority_id:     "authority-wfo",
+      deleted:          false,
+      department:       "",
+      work_preferences: 7.times.map do |i|
         {
-          day_of_week: 6,
-          start_time:  9,
-          end_time:    17,
+          day_of_week: i,
+          start_time:  (Time.utc - 4.hours).hour,
+          end_time:    (Time.utc + 4.hours).hour,
           location:    "wfo",
-        },
-      ],
+        }
+      end,
       work_overrides: {
         "2024-02-15": {
           day_of_week: 4,
@@ -114,7 +218,7 @@ class StaffAPI < DriverSpecs::MockDriver
       },
       sys_admin:   false,
       support:     false,
-      email:       "user_one@example.com",
+      email:       "user_two@example.com",
       phone:       "",
       ui_theme:    "light",
       login_name:  "",
@@ -122,7 +226,46 @@ class StaffAPI < DriverSpecs::MockDriver
       card_number: "",
     }
 
-    JSON.parse(user.to_json)
+    case id
+    when "user-wfh"
+      JSON.parse(user_wfh.to_json)
+      # when "user-aol"
+      #   JSON.parse(user_wfh.to_json)
+    when "user-wfo"
+      JSON.parse(user_wfo.to_json)
+    else
+      JSON.parse(user_wfh.to_json)
+    end
+  end
+
+  def zones(q : String? = nil,
+            limit : Int32 = 1000,
+            offset : Int32 = 0,
+            parent : String? = nil,
+            tags : Array(String) | String? = nil)
+    zones = [
+      {
+        created_at:   1660537814,
+        updated_at:   1681800971,
+        id:           "zone-1234",
+        name:         "Test Zone",
+        display_name: "Test Zone",
+        location:     "",
+        description:  "",
+        code:         "",
+        type:         "",
+        count:        0,
+        capacity:     0,
+        map_id:       "",
+        tags:         [
+          "building",
+        ],
+        triggers:  [] of String,
+        parent_id: "zone-0000",
+      },
+    ]
+
+    JSON.parse(zones.to_json)
   end
 end
 
@@ -161,14 +304,60 @@ class Mailer < DriverSpecs::MockDriver
   end
 end
 
-DriverSpecs.mock_driver "Place::StaffAPI" do
+DriverSpecs.mock_driver "Place::AutoRelease" do
   system({
     StaffAPI: {StaffAPI},
     Mailer:   {Mailer},
   })
 
-  _resp = exec(:pending_release).get
-  # _resp = exec(:get_user_preferences, "user-wYLBwmC7GFbupt").get
+  settings({
+    time_window_hours: 8,
+    auto_release:      {
+      time_before: 10,
+      time_after:  10,
+      resources:   ["desk"],
+    },
+  })
+
+  resp = exec(:get_building_id).get
+  resp.should eq "zone-1234"
+
+  resp = exec(:enabled?).get
+  resp.should eq true
+
+  resp = exec(:get_pending_bookings).get
+  resp.not_nil!.as_a.size.should eq 5
+
+  resp = exec(:get_user_preferences?, "user-wfh").get
+  resp.not_nil!.as_h.keys.should eq ["work_preferences", "work_overrides"]
+
+  # Should only have 3 pending releases (ignore, notify, reject)
+  resp = exec(:pending_release).get
+  pending_release = resp.not_nil!.as_a.map(&.as_h["title"])
+  pending_release.size.should eq 3
+  pending_release.should eq ["ignore", "notify", "reject"]
+
+  # Should only reject one booking (booking_id: 3, title: reject)
+  resp = exec(:release_bookings).get
+  resp.should eq [3]
+  system(:StaffAPI_1)[:rejected].should eq 1
+
+  # Don't try to reject bookings that have already been rejected
+  resp = exec(:release_bookings).get
+  resp.should eq [3]
+  system(:StaffAPI_1)[:rejected].should eq 1
+
+  # Send email once booking is past the time_before window,
+  # but before the time_after window
+  # (booking_id: 2, title: notify)
+  resp = exec(:send_release_emails).get
+  resp.should eq [2]
+  system(:Mailer_1)[:sent].should eq 1
+
+  # Spam protection, should not send email again
+  resp = exec(:send_release_emails).get
+  resp.should eq [2]
+  system(:Mailer_1)[:sent].should eq 1
 
-  # system(:Mailer_1)[:sent].should eq 1
+  # TODO: test work_overrides
 end