diff --git a/lua/orgmode/org/indent.lua b/lua/orgmode/org/indent.lua
index 8474b6250..6ce26713d 100644
--- a/lua/orgmode/org/indent.lua
+++ b/lua/orgmode/org/indent.lua
@@ -175,27 +175,34 @@ local get_matches = ts_utils.memoize_by_buf_tick(function(bufnr)
         indent = new_header_indent,
       })
 
-      local content_indent_pad = 0
+      local content_indent_pad
       -- Only include the header line and the content. Do not include the footer in the loop.
       for i = range.start.line + 1, range['end'].line - 2 do
-        local curr_indent = vim.fn.indent(i + 1)
-        -- Correctly align the pad to the new header position if it was underindented
-        local new_indent_pad = new_header_indent - curr_indent
-        -- If the current content indentaion is less than the new header indent we want to increase all of the
-        -- content by the largest difference in indentation between a given content line and the new header indent.
-        if curr_indent < new_header_indent then
-          content_indent_pad = math.max(new_indent_pad, content_indent_pad)
-        else
-          -- If the current content indentation is more than the new header indentation, but it was the current
-          -- content indentation was less than the current header indent then we want to add some indentation onto
-          -- the content by the largest negative difference (meaning -1 > -2 > -3 so take -1 as the pad).
-          --
-          -- We do a check for 0 here as we don't want to do a max of neg number against 0. 0 will always win. As
-          -- such if the current pad is 0 just set to the new calculated pad.
-          if content_indent_pad == 0 then
-            content_indent_pad = new_indent_pad
+        local linenr = i + 1
+        local line_content = vim.api.nvim_buf_get_lines(bufnr, linenr - 1, linenr, true)[1]
+        -- If the line is blank, we should ignore it as `vim.fn.indent` will return a 0 indent for
+        -- it which may be less indented than the header indentation. We shouldn't factor in blank
+        -- lines for indentation.
+        if not line_content:match('^$') then
+          local curr_indent = vim.fn.indent(linenr)
+          -- Correctly align the pad to the new header position if it was underindented
+          local new_indent_pad = new_header_indent - curr_indent
+          -- If the current content indentaion is less than the new header indent we want to increase all of the
+          -- content by the largest difference in indentation between a given content line and the new header indent.
+          if curr_indent < new_header_indent then
+            content_indent_pad = math.max(new_indent_pad, content_indent_pad or 0)
           else
-            content_indent_pad = math.max(new_indent_pad, content_indent_pad)
+            -- If the current content indentation is more than the new header indentation, but it was the current
+            -- content indentation was less than the current header indent then we want to add some indentation onto
+            -- the content by the largest negative difference (meaning -1 > -2 > -3 so take -1 as the pad).
+            --
+            -- We do a check for 0 here as we don't want to do a max of neg number against 0. 0 will always win. As
+            -- such if the current pad is 0 just set to the new calculated pad.
+            if not content_indent_pad then
+              content_indent_pad = new_indent_pad
+            else
+              content_indent_pad = math.max(new_indent_pad, content_indent_pad)
+            end
           end
         end
       end
diff --git a/tests/plenary/org/indent_spec.lua b/tests/plenary/org/indent_spec.lua
index e7b0292d8..f52e34337 100644
--- a/tests/plenary/org/indent_spec.lua
+++ b/tests/plenary/org/indent_spec.lua
@@ -62,6 +62,23 @@ local function test_full_reindent()
     '           "another key": "another value"',
     '         }',
     '         #+END_SRC',
+    '    - Correctly maintains indentation when single line is at the same level as header and rest is overindented',
+    '      #+BEGIN_SRC json',
+    '      {',
+    '           "key": "value",',
+    '           "another key": "another value"',
+    '               }',
+    '      #+END_SRC',
+    '    - Correctly ignores blank lines for calculating indentation',
+    '      #+BEGIN_SRC json',
+    '',
+    '          {',
+    '            "key": "value",',
+    '',
+    '            "another key": "another value"',
+    '          }',
+    '',
+    '      #+END_SRC',
   }
   helpers.create_file(unformatted_file)
   vim.cmd([[silent norm 0gg=G]])
@@ -118,6 +135,23 @@ local function test_full_reindent()
       '        "another key": "another value"',
       '      }',
       '      #+END_SRC',
+      '    - Correctly maintains indentation when single line is at the same level as header and rest is overindented',
+      '      #+BEGIN_SRC json',
+      '      {',
+      '           "key": "value",',
+      '           "another key": "another value"',
+      '               }',
+      '      #+END_SRC',
+      '    - Correctly ignores blank lines for calculating indentation',
+      '      #+BEGIN_SRC json',
+      '',
+      '      {',
+      '        "key": "value",',
+      '',
+      '        "another key": "another value"',
+      '      }',
+      '',
+      '      #+END_SRC',
     }
   else
     expected = {
@@ -171,6 +205,23 @@ local function test_full_reindent()
       '    "another key": "another value"',
       '  }',
       '  #+END_SRC',
+      '- Correctly maintains indentation when single line is at the same level as header and rest is overindented',
+      '  #+BEGIN_SRC json',
+      '  {',
+      '       "key": "value",',
+      '       "another key": "another value"',
+      '           }',
+      '  #+END_SRC',
+      '- Correctly ignores blank lines for calculating indentation',
+      '  #+BEGIN_SRC json',
+      '',
+      '  {',
+      '    "key": "value",',
+      '',
+      '    "another key": "another value"',
+      '  }',
+      '',
+      '  #+END_SRC',
     }
   end
   expect_whole_buffer(expected)