diff --git a/lua/orgmode/org/hyperlinks/init.lua b/lua/orgmode/org/hyperlinks/init.lua
index 2dc6a5d7a..a1e163d3b 100644
--- a/lua/orgmode/org/hyperlinks/init.lua
+++ b/lua/orgmode/org/hyperlinks/init.lua
@@ -24,20 +24,13 @@ function Hyperlinks.find_by_filepath(url)
     return {}
   end
   --TODO integrate with orgmode.utils.fs or orgmode.objects.url
-  local file_base_no_start_path = vim.pesc(file_base:gsub('^%./', '') .. '')
-  local is_relative_path = file_base:match('^%./')
-  local current_file_directory = vim.pesc(fs.get_current_file_dir())
   local valid_filenames = {}
   for _, f in ipairs(filenames) do
-    if is_relative_path then
-      local match = f:match('^' .. current_file_directory .. '/(' .. file_base_no_start_path .. '.*%.org)$')
-      if match then
-        table.insert(valid_filenames, './' .. match)
-      end
-    else
-      if f:find('^' .. file_base) then
-        table.insert(valid_filenames, f)
+    if f:find('^' .. file_base) then
+      if url.realpath then
+        f = f:gsub(file_base, url.path)
       end
+      table.insert(valid_filenames, f)
     end
   end
 
diff --git a/lua/orgmode/org/hyperlinks/url.lua b/lua/orgmode/org/hyperlinks/url.lua
index f1bc5c3b6..cc7ea900e 100644
--- a/lua/orgmode/org/hyperlinks/url.lua
+++ b/lua/orgmode/org/hyperlinks/url.lua
@@ -1,3 +1,4 @@
+local fs = require('orgmode.utils.fs')
 ---@alias OrgUrlPathType 'file' | 'headline' | 'custom-id' | 'id' | 'external-url' | 'plain' | nil
 ---@alias OrgUrlTargetType 'headline' | 'custom-id' | 'line-number' | 'unknown' | nil
 
@@ -116,7 +117,7 @@ function Url:get_file()
   if not self:is_file() then
     return nil
   end
-  return self.path
+  return self.realpath or self.path
 end
 
 ---@return string | nil
@@ -246,8 +247,12 @@ function Url:_parse_path_type()
     return
   end
 
-  if first_char == '.' and (self.path:sub(1, 3) == '../' or self.path:sub(1, 2) == './') then
+  if
+    (first_char == '.' and (self.path:sub(1, 3) == '../' or self.path:sub(1, 2) == './'))
+    or (first_char == '~' and self.path:sub(2, 2) == '/')
+  then
     self.path_type = 'file'
+    self.realpath = fs.get_real_path(self.path) or self.path
     return
   end
 
diff --git a/lua/orgmode/utils/fs.lua b/lua/orgmode/utils/fs.lua
index cf2329e8d..a131773b7 100644
--- a/lua/orgmode/utils/fs.lua
+++ b/lua/orgmode/utils/fs.lua
@@ -30,6 +30,10 @@ function M.get_real_path(filepath)
     return false
   end
   local real = vim.loop.fs_realpath(substituted)
+  if filepath:sub(-1, -1) == '/' then
+    -- make sure if filepath gets a trailing slash, the realpath gets one, too.
+    real = real .. '/'
+  end
   return real or false
 end
 
diff --git a/tests/plenary/helpers.lua b/tests/plenary/helpers.lua
index 3f7ca69f8..9df05d9f8 100644
--- a/tests/plenary/helpers.lua
+++ b/tests/plenary/helpers.lua
@@ -35,8 +35,38 @@ local function create_file_instance(lines, filename)
   return file
 end
 
+---@return table
+local function create_agenda_files(filenames, contents)
+  -- NOTE: content is only 1 line for 1 file
+  local temp_fname = vim.fn.tempname()
+  local temp_dir = vim.fn.fnamemodify(temp_fname, ':p:h')
+  -- clear temp dir
+  vim.fn.delete(temp_dir .. '/*', 'rf')
+  local files = {}
+  local agenda_files = {}
+  for i, filename in ipairs(filenames) do
+    local fname = temp_dir .. '/' .. filename
+    fname = vim.fn.fnamemodify(fname, ':p')
+    if fname then
+      local dir = vim.fn.fnamemodify(fname, ':p:h')
+      vim.fn.mkdir(dir, 'p')
+      vim.fn.writefile({ contents[i] }, fname)
+      files[filename] = fname
+      table.insert(agenda_files, fname)
+    end
+  end
+  local cfg = vim.tbl_extend('force', {
+    org_agenda_files = agenda_files,
+  }, {})
+  local org = orgmode.setup(cfg)
+  org:init()
+  return files
+end
+
 return {
+  load_file = load_file,
   create_file = create_file,
   create_file_instance = create_file_instance,
   create_agenda_file = create_agenda_file,
+  create_agenda_files = create_agenda_files,
 }
diff --git a/tests/plenary/org/autocompletion_spec.lua b/tests/plenary/org/autocompletion_spec.lua
index c04bc1556..4465eaa90 100644
--- a/tests/plenary/org/autocompletion_spec.lua
+++ b/tests/plenary/org/autocompletion_spec.lua
@@ -339,6 +339,39 @@ describe('Autocompletion', function()
           { menu = '[Org]', word = 'Title without anchor' },
         }, result)
       end)
+
+      it('should work on relative paths', function()
+        local files = helpers.create_agenda_files({
+          'a.org',
+          'b/c.org',
+        }, {
+          '[[./  ',
+          '[[../  ',
+        })
+        helpers.load_file(files['b/c.org'])
+        vim.fn.cursor({ 1, 6 })
+
+        assert.are.same({
+          { menu = '[Org]', word = '../a.org' },
+          { menu = '[Org]', word = '../b/c.org' },
+        }, org.completion:omnifunc(0, '../'))
+      end)
+      it('should work on relative paths', function()
+        local files = helpers.create_agenda_files({
+          'a.org',
+          'b/c.org',
+        }, {
+          '[[./  ',
+          '[[../  ',
+        })
+        helpers.load_file(files['a.org'])
+        vim.fn.cursor({ 1, 5 })
+
+        assert.are.same({
+          { menu = '[Org]', word = './a.org' },
+          { menu = '[Org]', word = './b/c.org' },
+        }, org.completion:omnifunc(0, './'))
+      end)
     end)
   end)
 end)