diff --git a/lua/orgmode/clock/init.lua b/lua/orgmode/clock/init.lua
index 20020eb09..19d5d6001 100644
--- a/lua/orgmode/clock/init.lua
+++ b/lua/orgmode/clock/init.lua
@@ -26,11 +26,20 @@ function Clock:init()
   end
 end
 
+function Clock:update_clocked_headline()
+  local last_clocked_headline = self.files:get_clocked_headline()
+  if last_clocked_headline and last_clocked_headline:is_clocked_in() then
+    self.clocked_headline = last_clocked_headline
+  end
+end
+
 function Clock:has_clocked_headline()
+  self:update_clocked_headline()
   return self.clocked_headline ~= nil
 end
 
 function Clock:org_clock_in()
+  self:update_clocked_headline()
   local item = self.files:get_closest_headline()
   if item:is_clocked_in() then
     return utils.echo_info(string.format('Clock continues in "%s"', item:get_title()))
@@ -53,6 +62,7 @@ function Clock:org_clock_in()
 end
 
 function Clock:org_clock_out()
+  self:update_clocked_headline()
   if not self.clocked_headline or not self.clocked_headline:is_clocked_in() then
     return
   end
@@ -62,6 +72,7 @@ function Clock:org_clock_out()
 end
 
 function Clock:org_clock_cancel()
+  self:update_clocked_headline()
   if not self.clocked_headline or not self.clocked_headline:is_clocked_in() then
     return utils.echo_info('No active clock')
   end
@@ -72,6 +83,7 @@ function Clock:org_clock_cancel()
 end
 
 function Clock:org_clock_goto()
+  self:update_clocked_headline()
   if not self.clocked_headline then
     return utils.echo_info('No active or recent clock task')
   end
diff --git a/tests/plenary/ui/clock_spec.lua b/tests/plenary/ui/clock_spec.lua
index 39f2d7fed..6ee39ba92 100644
--- a/tests/plenary/ui/clock_spec.lua
+++ b/tests/plenary/ui/clock_spec.lua
@@ -1,5 +1,6 @@
 local helpers = require('tests.plenary.helpers')
 local Date = require('orgmode.objects.date')
+local orgmode = require('orgmode')
 
 describe('Clock', function()
   local files = {}
@@ -149,4 +150,39 @@ describe('Clock', function()
     assert.are.same('', vim.fn.getline(6))
     assert.are.same('', vim.fn.getline(7))
   end)
+
+  it('should properly clock in an entry if unsaved edits were made to the buffer', function()
+    local file = helpers.create_agenda_file({
+      '* TODO Test 1',
+      '  :LOGBOOK:',
+      '  CLOCK: [2024-05-22 Wed 05:15]',
+      '  :END:',
+      '* TODO Test 2',
+    })
+
+    vim.cmd('edit ' .. file.filename)
+
+    -- Establish baseline: Test 1 is clocked in
+    local clock = orgmode.clock
+    assert.are.same('Test 1', clock.clocked_headline:get_title())
+    assert.is_true(clock.clocked_headline:is_clocked_in())
+
+    -- Move the test 2 header above test 1 and then clock test 2 in
+    vim.fn.cursor({ 5, 1 })
+    vim.cmd([[norm dd]])
+    vim.fn.cursor({ 1, 1 })
+    vim.cmd([[norm P]])
+    vim.fn.cursor({ 1, 1 })
+    clock:org_clock_in():wait()
+    file:reload():wait()
+
+    -- Test 2 is properly clocked in
+    assert.are.same('Test 2', clock.clocked_headline:get_title())
+    assert.are.same('Test 2', file:get_headlines()[1]:get_title())
+    assert.is_true(file:get_headlines()[1]:is_clocked_in())
+
+    -- Test 1 is properly clocked out
+    assert.are.same('Test 1', file:get_headlines()[2]:get_title())
+    assert.is_false(file:get_headlines()[2]:is_clocked_in())
+  end)
 end)