diff --git a/src/nvim/statusline.c b/src/nvim/statusline.c
index 1ac013f43b..017064c9e5 100644
--- a/src/nvim/statusline.c
+++ b/src/nvim/statusline.c
@@ -1119,16 +1119,19 @@ int build_stl_str_hl(win_T *wp, char *out, size_t outlen, char *fmt, OptIndex op
         }
       }
 
+      int minwid = stl_items[stl_groupitems[groupdepth]].minwid;
+
       // If the group is longer than it is allowed to be truncate by removing
       // bytes from the start of the group text. Don't truncate when item is a
       // 'statuscolumn' fold item to ensure correctness of the mouse clicks.
       if (group_len > stl_items[stl_groupitems[groupdepth]].maxwid
           && stl_items[stl_groupitems[groupdepth]].type != HighlightFold) {
         // { Determine the number of bytes to remove
+        int maxwid = stl_items[stl_groupitems[groupdepth]].maxwid;
 
         // Find the first character that should be included.
         int n = 0;
-        while (group_len >= stl_items[stl_groupitems[groupdepth]].maxwid) {
+        while (group_len >= maxwid) {
           group_len -= ptr2cells(t + n);
           n += utfc_ptr2len(t + n);
         }
@@ -1141,7 +1144,8 @@ int build_stl_str_hl(win_T *wp, char *out, size_t outlen, char *fmt, OptIndex op
         memmove(t + 1, t + n, (size_t)(out_p - (t + n)));
         out_p = out_p - n + 1;
         // Fill up space left over by half a double-wide char.
-        while (++group_len < stl_items[stl_groupitems[groupdepth]].minwid) {
+        minwid = MIN(minwid, maxwid);
+        while (++group_len < minwid) {
           schar_get_adv(&out_p, fillchar);
         }
         // }
@@ -1157,33 +1161,36 @@ int build_stl_str_hl(win_T *wp, char *out, size_t outlen, char *fmt, OptIndex op
           stl_items[idx].start = MAX(stl_items[idx].start, t);
         }
         // If the group is shorter than the minimum width, add padding characters.
-      } else if (abs(stl_items[stl_groupitems[groupdepth]].minwid) > group_len) {
-        ptrdiff_t min_group_width = stl_items[stl_groupitems[groupdepth]].minwid;
+      } else if (abs(minwid) > group_len) {
+        ptrdiff_t fillchar_bytes = (ptrdiff_t)schar_len(fillchar);
         // If the group is left-aligned, add characters to the right.
-        if (min_group_width < 0) {
-          min_group_width = 0 - min_group_width;
-          while (group_len++ < min_group_width && out_p < out_end_p) {
+        if (minwid < 0) {
+          minwid = 0 - minwid;
+          while (group_len++ < minwid && out_p + fillchar_bytes <= out_end_p) {
             schar_get_adv(&out_p, fillchar);
           }
           // If the group is right-aligned, shift everything to the right and
           // prepend with filler characters.
         } else {
-          // { Move the group to the right
-          group_len = (min_group_width - group_len) * (int)schar_len(fillchar);
-          memmove(t + group_len, t, (size_t)(out_p - t));
-          if (out_p + group_len >= (out_end_p + 1)) {
-            group_len = out_end_p - out_p;
+          ptrdiff_t added_cells = minwid - group_len;
+          ptrdiff_t added_bytes = added_cells * fillchar_bytes;
+          if (out_p + added_bytes > out_end_p) {
+            added_cells = (out_end_p - out_p) / fillchar_bytes;
+            added_bytes = added_cells * fillchar_bytes;
           }
-          out_p += group_len;
+
+          // { Move the group to the right
+          memmove(t + added_bytes, t, (size_t)(out_p - t));
+          out_p += added_bytes;
           // }
 
           // Adjust item start positions
           for (int n = stl_groupitems[groupdepth] + 1; n < curitem; n++) {
-            stl_items[n].start += group_len;
+            stl_items[n].start += added_bytes;
           }
 
           // Prepend the fill characters
-          for (; group_len > 0; group_len--) {
+          for (; added_cells > 0; added_cells--) {
             schar_get_adv(&t, fillchar);
           }
         }
diff --git a/test/unit/statusline_spec.lua b/test/unit/statusline_spec.lua
index 1388063a92..abf45474bb 100644
--- a/test/unit/statusline_spec.lua
+++ b/test/unit/statusline_spec.lua
@@ -429,6 +429,40 @@ describe('build_stl_str_hl', function()
     'aaaa~~b~~c~~d~~e~~fg~~hi~~jk~~lmnop~~qrstuv~~~wxyz'
   )
 
+  -- item group testing
+
+  statusline_test_align(
+    'should right align in right aligned groups',
+    30,
+    '%5(%l%), %5.(%l%), %5.5(%l%), %5.10(%l%)',
+    '~~~~0, ~~~~0, ~~~~0, ~~~~0',
+    { expected_cell_count = 26 }
+  )
+
+  statusline_test_align(
+    'should left align in left aligned groups',
+    30,
+    '%-5(%l%), %-5.(%l%), %-5.5(%l%), %-5.10(%l%)',
+    '0~~~~, 0~~~~, 0~~~~, 0~~~~',
+    { expected_cell_count = 26 }
+  )
+
+  statusline_test(
+    'Should truncate groups according to maxwid',
+    30,
+    '%.5(1234567%), %2.5(1234567%), %5.5(1234567%)',
+    '<4567, <4567, <4567',
+    { expected_cell_count = 19 }
+  )
+
+  statusline_test_align(
+    'Should compensate with fillchar after truncating item group at multicell character',
+    20,
+    '%.5(12🙂345%), %5.5(12🙂345%), %50.5(12🙂345%)',
+    '<345, <345~, <345~',
+    { expected_cell_count = 18 }
+  )
+
   -- stl item testing
   local tabline = ''
   for i = 1, 1000 do