diff --git a/lib/reline/line_editor.rb b/lib/reline/line_editor.rb
index 763a2171e5..c777f45ab9 100644
--- a/lib/reline/line_editor.rb
+++ b/lib/reline/line_editor.rb
@@ -403,6 +403,27 @@ def calculate_overlay_levels(overlay_levels)
     levels
   end
 
+  def render_line_item(x, content)
+    segments = Reline::Unicode.split_ambiguous_emoji(content)
+    if segments
+      Reline::IOGate.write Reline::IOGate.reset_color_sequence
+      segments.each do |segment, ambiguous|
+        w = Reline::Unicode.calculate_width(segment, true)
+        Reline::IOGate.move_cursor_column(x)
+        if ambiguous
+          Reline::IOGate.write(' ' * w)
+          Reline::IOGate.move_cursor_column(x)
+        end
+        Reline::IOGate.write(segment)
+        x += w
+      end
+      Reline::IOGate.write Reline::IOGate.reset_color_sequence
+    else
+      Reline::IOGate.move_cursor_column(x)
+      Reline::IOGate.write "#{Reline::IOGate.reset_color_sequence}#{content}#{Reline::IOGate.reset_color_sequence}"
+    end
+  end
+
   def render_line_differential(old_items, new_items)
     old_levels = calculate_overlay_levels(old_items.zip(new_items).each_with_index.map {|((x, w, c), (nx, _nw, nc)), i| [x, w, c == nc && x == nx ? i : -1] if x }.compact)
     new_levels = calculate_overlay_levels(new_items.each_with_index.map { |(x, w), i| [x, w, i] if x }.compact).take(screen_width)
@@ -422,8 +443,7 @@ def render_line_differential(old_items, new_items)
         unless x == base_x && w == width
           content, pos = Reline::Unicode.take_mbchar_range(content, base_x - x, width, cover_begin: cover_begin, cover_end: cover_end, padding: true)
         end
-        Reline::IOGate.move_cursor_column x + pos
-        Reline::IOGate.write "#{Reline::IOGate.reset_color_sequence}#{content}#{Reline::IOGate.reset_color_sequence}"
+        render_line_item(x + pos, content)
       end
       base_x += width
     end
diff --git a/lib/reline/unicode.rb b/lib/reline/unicode.rb
index 28d6b1b2b9..c74df72341 100644
--- a/lib/reline/unicode.rb
+++ b/lib/reline/unicode.rb
@@ -41,6 +41,11 @@ class Reline::Unicode
   OSC_REGEXP = /\e\]\d+(?:;[^;\a\e]+)*(?:\a|\e\\)/
   WIDTH_SCANNER = /\G(?:(#{NON_PRINTING_START})|(#{NON_PRINTING_END})|(#{CSI_REGEXP})|(#{OSC_REGEXP})|(\X))/o
 
+  AMBIGUOUS_WIDTH_EMOJI_CLUSTER = Regexp.union(
+    /\p{Grapheme_Cluster_Break=Regional_Indicator}{2}/, # Flag emoji
+    /\p{Extended_Pictographic}\u{FE0F}/ # Variation selector-16
+  )
+
   def self.escape_for_print(str)
     str.chars.map! { |gr|
       case gr
@@ -78,6 +83,20 @@ def self.east_asian_width(ord)
     size == -1 ? Reline.ambiguous_width : size
   end
 
+  # Some emoji needs special handling on rendering because width is ambiguous depending on terminal emulator and configuration.
+  # For example, iTerm can configure flag-emoji width and variation selector 16 emoji width.
+  #   split_ambiguous_emoji('abc') #=> nil (no ambiguous emoji)
+  #   split_ambiguous_emoji('abc[flag][flag]de') #=> [['abc', false], ['[flag]', true], ['[flag]', true], ['de', false]]
+  def self.split_ambiguous_emoji(str)
+    return if str.ascii_only? || !str.match?(AMBIGUOUS_WIDTH_EMOJI_CLUSTER)
+
+    str.grapheme_clusters.chunk.with_index do |gc, idx|
+      gc.match?(AMBIGUOUS_WIDTH_EMOJI_CLUSTER) ? idx : -1
+    end.map do |key, gcs|
+      [gcs.join, key != -1]
+    end
+  end
+
   def self.get_mbchar_width(mbchar)
     ord = mbchar.ord
     if ord <= 0x1F # in EscapedPairs
@@ -87,8 +106,16 @@ def self.get_mbchar_width(mbchar)
     end
 
     utf8_mbchar = mbchar.encode(Encoding::UTF_8)
+    return east_asian_width(utf8_mbchar.ord) if utf8_mbchar.size == 1
+
+    width = 0
+    if utf8_mbchar.match?(AMBIGUOUS_WIDTH_EMOJI_CLUSTER)
+      width += 2
+      utf8_mbchar = utf8_mbchar.sub(AMBIGUOUS_WIDTH_EMOJI_CLUSTER, '')
+    end
+
     zwj = false
-    utf8_mbchar.chars.sum do |c|
+    width + utf8_mbchar.chars.sum do |c|
       if zwj
         zwj = false
         0
diff --git a/test/reline/test_line_editor.rb b/test/reline/test_line_editor.rb
index 28fcbfa6df..94141e66a6 100644
--- a/test/reline/test_line_editor.rb
+++ b/test/reline/test_line_editor.rb
@@ -242,6 +242,14 @@ def test_complicated
         @line_editor.render_line_differential(state_b, state_a)
       end
     end
+
+    def test_ambiguous_emoji
+      state_a = [nil]
+      state_b = [[0, 12, '😄😄©️🇯🇵😄😄']]
+      assert_output '[COL_0]😄😄[COL_4]  [COL_4]©️[COL_6]  [COL_6]🇯🇵[COL_8]😄😄' do
+        @line_editor.render_line_differential(state_a, state_b)
+      end
+    end
   end
 
   def test_menu_info_format
diff --git a/test/reline/test_unicode.rb b/test/reline/test_unicode.rb
index d86dc4d759..efa7576f6e 100644
--- a/test/reline/test_unicode.rb
+++ b/test/reline/test_unicode.rb
@@ -296,6 +296,15 @@ def test_halfwidth_dakuten_handakuten_combinations
     assert_equal 3, Reline::Unicode.get_mbchar_width("紅ﾞ")
   end
 
+  def test_split_ambiguous_emoji
+    variant_selector_emoji = "©️"
+    flag_emoji = '🇯🇵'
+    normal_text = '😀abc😀👨‍👩‍👧'
+    text_target = normal_text + variant_selector_emoji + flag_emoji + normal_text + flag_emoji + normal_text
+    expected = [[normal_text, false], [variant_selector_emoji, true], [flag_emoji, true], [normal_text, false], [flag_emoji, true], [normal_text, false]]
+    assert_equal expected, Reline::Unicode.split_ambiguous_emoji(text_target)
+  end
+
   def test_grapheme_cluster_width
     # GB6, GB7, GB8: Hangul syllable
     assert_equal 2, Reline::Unicode.get_mbchar_width('한'.unicode_normalize(:nfd))