diff --git a/.ameba.yml b/.ameba.yml
index 77817000..ffcda9ec 100644
--- a/.ameba.yml
+++ b/.ameba.yml
@@ -40,3 +40,5 @@ Lint/NotNil:
 Documentation/DocumentationAdmonition:
   Enabled: false
 
+Metrics/CyclomaticComplexity:
+  Enabled: false
diff --git a/spec/commands/time_worked/week_spec.cr b/spec/commands/time_worked/week_spec.cr
index c398a717..288e4874 100644
--- a/spec/commands/time_worked/week_spec.cr
+++ b/spec/commands/time_worked/week_spec.cr
@@ -252,6 +252,169 @@ describe TandaCLI::Commands::TimeWorked::Week do
       context.stdout.to_s.should eq(expected)
     end
   end
+
+  it "Display assumes expected finish date for clock out if forgotten" do
+    WebMock
+      .stub(:get, endpoint(Regex.new("/shifts")))
+      .to_return(
+        status: 200,
+        body: [
+          build_shift(
+            id: 1,
+            start: Time.local(2024, 12, 23, 8, 30),
+            finish: nil,
+            break_start: Time.local(2024, 12, 23, 12),
+            break_finish: Time.local(2024, 12, 23, 12, 30)
+          ),
+          build_shift(
+            id: 2,
+            start: Time.local(2024, 12, 24, 8, 30),
+            finish: nil,
+            break_start: Time.local(2024, 12, 24, 12),
+            break_finish: Time.local(2024, 12, 24, 12, 30)
+          ),
+        ].to_json,
+      )
+
+    travel_to(Time.local(2024, 12, 24, 14)) do
+      context = run(["time_worked", "week", "--display"])
+
+      expected = <<-OUTPUT.gsub("<space>", " ")
+      ⚠️ Warning: Missing finish time for Monday, assuming regular hours finish time
+      Time worked: 8 hours and 0 minutes
+      📅 Monday, 23 Dec 2024
+      🕓 8:30 am - 5:00 pm
+      🚧 Pending
+      ☕️ Breaks:
+          🕓 12:00 pm - 12:30 pm
+          ⏸️  30 minutes
+          💰 false
+
+      Worked so far: 5 hours and 0 minutes
+      📅 Tuesday, 24 Dec 2024
+      🕓 8:30 am -<space>
+      🚧 Pending
+      ☕️ Breaks:
+          🕓 12:00 pm - 12:30 pm
+          ⏸️  30 minutes
+          💰 false
+
+      Time left today: 3 hours and 0 minutes
+      You can clock out at: 5:00 pm
+
+      You've worked 13 hours and 0 minutes this week
+
+      OUTPUT
+
+      context.stdout.to_s.should eq(expected)
+    end
+  end
+
+  it "Shows overtime if previous day filled and past expected finish" do
+    WebMock
+      .stub(:get, endpoint(Regex.new("/shifts")))
+      .to_return(
+        status: 200,
+        body: [
+          build_shift(
+            id: 1,
+            start: Time.local(2024, 12, 23, 8, 30),
+            finish: nil,
+            break_start: Time.local(2024, 12, 23, 12),
+            break_finish: Time.local(2024, 12, 23, 12, 30)
+          ),
+          build_shift(
+            id: 2,
+            start: Time.local(2024, 12, 24, 8, 30),
+            finish: nil,
+            break_start: Time.local(2024, 12, 24, 12),
+            break_finish: Time.local(2024, 12, 24, 12, 30)
+          ),
+        ].to_json,
+      )
+
+    travel_to(Time.local(2024, 12, 24, 19)) do
+      context = run(["time_worked", "week", "--display"])
+
+      expected = <<-OUTPUT.gsub("<space>", " ")
+      ⚠️ Warning: Missing finish time for Monday, assuming regular hours finish time
+      Time worked: 8 hours and 0 minutes
+      📅 Monday, 23 Dec 2024
+      🕓 8:30 am - 5:00 pm
+      🚧 Pending
+      ☕️ Breaks:
+          🕓 12:00 pm - 12:30 pm
+          ⏸️  30 minutes
+          💰 false
+
+      Worked so far: 10 hours and 0 minutes
+      📅 Tuesday, 24 Dec 2024
+      🕓 8:30 am -<space>
+      🚧 Pending
+      ☕️ Breaks:
+          🕓 12:00 pm - 12:30 pm
+          ⏸️  30 minutes
+          💰 false
+
+      Overtime this week: 2 hours and 0 minutes
+      Overtime since: 5:00 pm
+
+      You've worked 18 hours and 0 minutes this week
+
+      OUTPUT
+
+      context.stdout.to_s.should eq(expected)
+    end
+  end
+
+  it "Doesn't show time left or overtime if next day with assumed regular hours without breaks" do
+    WebMock
+      .stub(:get, endpoint(Regex.new("/shifts")))
+      .to_return(
+        status: 200,
+        body: [
+          build_shift(
+            id: 1,
+            start: Time.local(2024, 12, 23, 8, 30),
+            finish: nil,
+            break_start: nil,
+            break_finish: nil
+          ),
+          build_shift(
+            id: 2,
+            start: Time.local(2024, 12, 24, 8, 30),
+            finish: nil,
+            break_start: nil,
+            break_finish: nil
+          ),
+        ].to_json,
+      )
+
+    travel_to(Time.local(2024, 12, 25, 1)) do
+      context = run(["time_worked", "week", "--display"])
+
+      expected = <<-OUTPUT.gsub("<space>", " ")
+      ⚠️ Warning: Missing finish time for Monday, assuming regular hours finish time
+      Time worked: 8 hours and 0 minutes
+      📅 Monday, 23 Dec 2024
+      🕓 8:30 am - 5:00 pm
+      🚧 Pending
+      ☕️ 30 minutes
+
+      ⚠️ Warning: Missing finish time for Tuesday, assuming regular hours finish time
+      Time worked: 8 hours and 0 minutes
+      📅 Tuesday, 24 Dec 2024
+      🕓 8:30 am - 5:00 pm
+      🚧 Pending
+      ☕️ 30 minutes
+
+      You've worked 16 hours and 0 minutes this week
+
+      OUTPUT
+
+      context.stdout.to_s.should eq(expected)
+    end
+  end
 end
 
 private def build_shift(id, start, finish, break_start, break_finish)
@@ -265,17 +428,19 @@ private def build_shift(id, start, finish, break_start, break_finish)
     break_finish: break_finish.try(&.to_unix),
     break_length: 30,
     breaks:       [
-      {
-        id:                               1,
-        selected_automatic_break_rule_id: nil,
-        shift_id:                         id,
-        start:                            break_start.try(&.to_unix),
-        finish:                           break_finish.try(&.to_unix),
-        length:                           30,
-        paid:                             false,
-        updated_at:                       1735259689,
-      },
-    ],
+      if break_start || break_finish
+        {
+          id:                               1,
+          selected_automatic_break_rule_id: nil,
+          shift_id:                         id,
+          start:                            break_start.try(&.to_unix),
+          finish:                           break_finish.try(&.to_unix),
+          length:                           30,
+          paid:                             false,
+          updated_at:                       1735259689,
+        }
+      end,
+    ].compact,
     finish:           finish.try(&.to_unix),
     department_id:    1,
     sub_cost_centre:  nil,
diff --git a/src/tanda_cli/executors/time_worked/base.cr b/src/tanda_cli/executors/time_worked/base.cr
index 97c36bd1..bf49fc3f 100644
--- a/src/tanda_cli/executors/time_worked/base.cr
+++ b/src/tanda_cli/executors/time_worked/base.cr
@@ -6,6 +6,7 @@ module TandaCLI
     module TimeWorked
       abstract class Base
         alias RegularHoursScheduleBreak = Configuration::Serialisable::Organisation::RegularHoursSchedule::Break
+        alias RegularHoursSchedule = Configuration::Serialisable::Organisation::RegularHoursSchedule
 
         def initialize(@context : Context, @display : Bool, @offset : Int32?); end
 
@@ -23,7 +24,7 @@ module TandaCLI
             .select(&.visible?)
         end
 
-        private def calculate_time_worked(shifts : Array(Types::Shift)) : Tuple(Time::Span, Time::Span)
+        private def calculate_time_worked(shifts : Array(Types::Shift), regular_hours_schedules : Array(RegularHoursSchedule)? = nil) : Tuple(Time::Span, Time::Span)
           total_time_worked = Time::Span.zero
           total_leave_hours = Time::Span.zero
 
@@ -42,7 +43,11 @@ module TandaCLI
             time_worked = shift.time_worked(treat_paid_breaks_as_unpaid)
             worked_so_far = shift.worked_so_far(treat_paid_breaks_as_unpaid)
 
-            print_shift(shift, time_worked, worked_so_far) if display?
+            if time_worked.nil? && shift.finish_time.nil? && regular_hours_schedules
+              time_worked = calculate_expected_time_worked(shift, treat_paid_breaks_as_unpaid, regular_hours_schedules)
+            end
+
+            print_shift(shift, time_worked, worked_so_far, regular_hours_schedules) if display?
 
             total_time = time_worked || worked_so_far
             total_time_worked += total_time if total_time
@@ -51,14 +56,24 @@ module TandaCLI
           {total_time_worked, total_leave_hours}
         end
 
-        private def print_shift(shift : Types::Shift, time_worked : Time::Span?, worked_so_far : Time::Span?)
+        private def print_shift(shift : Types::Shift, time_worked : Time::Span?, worked_so_far : Time::Span?, regular_hours_schedules : Array(RegularHoursSchedule)? = nil)
           if time_worked
             @context.display.puts "#{"Time worked:".colorize.white.bold} #{time_worked.hours} hours and #{time_worked.minutes} minutes"
           elsif worked_so_far
             @context.display.puts "#{"Worked so far:".colorize.white.bold} #{worked_so_far.hours} hours and #{worked_so_far.minutes} minutes"
           end
 
-          Representers::Shift.new(shift).display(@context.display)
+          expected_finish_time = nil
+          expected_break_length = nil
+          if shift.finish_time.nil? && regular_hours_schedules
+            schedule = regular_hours_schedules.find(&.day_of_week.==(shift.day_of_week))
+            if schedule && shift.date.date != Utils::Time.now.date
+              expected_finish_time = Utils::Time.pretty_time(schedule.finish_time)
+              expected_break_length = schedule.break_length
+            end
+          end
+
+          Representers::Shift.new(shift, expected_finish_time, expected_break_length).display(@context.display)
           @context.display.puts
         end
 
@@ -73,6 +88,33 @@ module TandaCLI
           Representers::LeaveRequest::DailyBreakdown.new(breakdown, leave_request).display(@context.display)
           @context.display.puts
         end
+
+        private def calculate_expected_time_worked(shift : Types::Shift, treat_paid_breaks_as_unpaid : Bool, regular_hours_schedules : Array(RegularHoursSchedule)) : Time::Span?
+          start_time = shift.start_time
+          return unless start_time
+
+          schedule = regular_hours_schedules.find(&.day_of_week.==(shift.day_of_week))
+          return unless schedule
+          return if shift.date.date == Utils::Time.now.date
+
+          if display?
+            @context.display.puts "#{"⚠️ Warning:".colorize.yellow.bold} Missing finish time for #{shift.date.to_s("%A")}, assuming regular hours finish time"
+          end
+
+          expected_finish = Time.local(
+            shift.date.year,
+            shift.date.month,
+            shift.date.day,
+            schedule.finish_time.hour,
+            schedule.finish_time.minute,
+            location: Utils::Time.location
+          )
+
+          actual_break_time = (treat_paid_breaks_as_unpaid ? shift.valid_breaks : shift.valid_breaks.reject(&.paid?)).sum(&.ongoing_length).minutes
+          expected_break_time = actual_break_time == 0.minutes ? schedule.break_length : 0.minutes
+          total_break_time = actual_break_time + expected_break_time
+          (expected_finish - start_time) - total_break_time
+        end
       end
     end
   end
diff --git a/src/tanda_cli/executors/time_worked/week.cr b/src/tanda_cli/executors/time_worked/week.cr
index c2c978b1..6fc5b7bd 100644
--- a/src/tanda_cli/executors/time_worked/week.cr
+++ b/src/tanda_cli/executors/time_worked/week.cr
@@ -17,7 +17,9 @@ module TandaCLI
           from ||= to.at_beginning_of_week(start_day)
           shifts = fetch_visible_shifts(from, to)
 
-          total_time_worked, total_leave_hours = calculate_time_worked(shifts)
+          organisation = @context.config.current_organisation!
+          regular_hours_schedules = organisation.regular_hours_schedules
+          total_time_worked, total_leave_hours = calculate_time_worked(shifts, regular_hours_schedules)
           if total_time_worked.zero? && total_leave_hours.zero?
             @context.display.puts "You haven't clocked in this week"
           else
diff --git a/src/tanda_cli/representers/shift.cr b/src/tanda_cli/representers/shift.cr
index 2da8c142..3f785d4a 100644
--- a/src/tanda_cli/representers/shift.cr
+++ b/src/tanda_cli/representers/shift.cr
@@ -8,27 +8,36 @@ require "../types/shift_break"
 module TandaCLI
   module Representers
     struct Shift < Base(Types::Shift)
+      def initialize(@object : Types::Shift, @expected_finish_time : String? = nil, @expected_break_length : Time::Span? = nil)
+      end
+
       private def build_display(builder : Builder)
         builder << "📅 #{@object.pretty_date}\n"
 
         pretty_start = @object.pretty_start_time
-        pretty_finish = @object.pretty_finish_time
+        pretty_finish = @object.pretty_finish_time || @expected_finish_time
+        pretty_finish = pretty_finish.colorize.yellow if pretty_finish && @expected_finish_time
         builder << "🕓 #{pretty_start} - #{pretty_finish}\n" if pretty_start || pretty_finish
 
         builder << "🚧 #{@object.status}\n"
 
-        build_shift_breaks(builder) if @object.valid_breaks.present?
+        build_shift_breaks(builder) if @object.valid_breaks.present? || @expected_break_length
         build_notes(builder) if @object.notes.present?
       end
 
       private def build_shift_breaks(builder : Builder)
-        builder << "☕️ Breaks:\n".colorize.white.bold
-        valid_breaks = @object.valid_breaks
-        last_break_index = valid_breaks.size - 1
-
-        valid_breaks.sort_by(&.id).each_with_index do |shift_break, index|
-          ShiftBreak.new(shift_break).build(builder)
-          builder << '\n' if index != last_break_index
+        expected_break_length = @expected_break_length
+
+        if (breaks = @object.valid_breaks).present?
+          builder << "☕️ Breaks:\n".colorize.white.bold
+          last_break_index = breaks.size - 1
+
+          breaks.sort_by(&.id).each_with_index do |shift_break, index|
+            ShiftBreak.new(shift_break).build(builder)
+            builder << '\n' if index != last_break_index
+          end
+        elsif expected_break_length && !expected_break_length.zero?
+          builder << "☕️ #{expected_break_length.total_minutes.to_i} minutes\n".colorize.yellow
         end
       end
 
diff --git a/src/tanda_cli/types/shift.cr b/src/tanda_cli/types/shift.cr
index eb94f21f..97819d3c 100644
--- a/src/tanda_cli/types/shift.cr
+++ b/src/tanda_cli/types/shift.cr
@@ -101,8 +101,9 @@ module TandaCLI
 
       def ongoing? : Bool
         return false unless start_time
+        return false unless finish_time.nil?
 
-        finish_time.nil?
+        date.date == Utils::Time.now.date
       end
 
       def ongoing_break? : Bool