diff --git a/SquirrelPanel.m b/SquirrelPanel.m
index 4fc684d7a..1674bf79c 100644
--- a/SquirrelPanel.m
+++ b/SquirrelPanel.m
@@ -4,7 +4,6 @@
 #import <QuartzCore/QuartzCore.h>
 
 @implementation NSBezierPath (BezierPathQuartzUtilities)
-// This method works only in OS X v10.2 and later.
 - (CGPathRef)quartzPath {
   if (@available(macOS 14.0, *)) {
     return self.CGPath;
@@ -96,11 +95,52 @@ - (void)formatMarkDown {
     [self deleteCharactersInRange:[result rangeAtIndex:1]];
     offset -= [result rangeAtIndex:6].length + [result rangeAtIndex:1].length;
   }];
-  if (offset != 0) { // no match. text remain unchanged.
+  if (offset != 0) { // repeat until no more nested markdown
     [self formatMarkDown];
   }
 }
 
+- (void)annotateRubyInVerticalLayout:(BOOL)vertical {
+  NSRegularExpression *regex = [[NSRegularExpression alloc] initWithPattern:@"(\\uFFF9)\\s*(\\w+?)\\s*((\\uFFFA)(.+?)(\\uFFFB))"
+                                  options:0 error:nil];
+  NSInteger __block offset = 0;
+  [regex enumerateMatchesInString:self.string options:0 range:NSMakeRange(0, self.length)
+                       usingBlock:^(NSTextCheckingResult *result, NSMatchingFlags flags, BOOL *stop) {
+    result = [result resultByAdjustingRangesWithOffset:offset];
+    if (@available(macOS 12.0, *)) {
+      NSString *rubyString = [self.string substringWithRange:[result rangeAtIndex:5]];
+      NSFont *baseFont = [self attribute:NSFontAttributeName atIndex:[result rangeAtIndex:2].location effectiveRange:NULL];
+      NSFont *rubyFont = [self attribute:NSFontAttributeName atIndex:[result rangeAtIndex:5].location effectiveRange:NULL];
+      rubyFont = [[NSFontManager sharedFontManager] convertFont:rubyFont toSize:[rubyFont pointSize] / 2];
+      CGFloat baselineOffset = vertical ? baseFont.verticalFont.ascender - rubyFont.verticalFont.descender : rubyFont.ascender + baseFont.descender;
+      NSColor *rubyColor = [self attribute:NSForegroundColorAttributeName atIndex:[result rangeAtIndex:5].location effectiveRange:NULL];
+      NSDictionary *rubyAttrs = @{NSFontAttributeName: rubyFont, NSForegroundColorAttributeName: rubyColor, CFBridgingRelease(kCTBaselineOffsetAttributeName): @(baselineOffset)};
+      NSArray<NSString *> *rubySubStrings = [rubyString componentsSeparatedByString:@" "];
+      NSRange baseRange = [result rangeAtIndex:2];
+      if (rubySubStrings.count > baseRange.length) {
+        rubySubStrings = @[rubyString];
+      }
+      for (NSUInteger i = 0; i < rubySubStrings.count; ++i) {
+        CTRubyAnnotationRef rubyAnnotation = CTRubyAnnotationCreateWithAttributes(kCTRubyAlignmentDistributeSpace, kCTRubyOverhangNone, kCTRubyPositionBefore, (__bridge CFStringRef)rubySubStrings[i], (__bridge CFDictionaryRef)rubyAttrs);
+        [self addAttribute:CFBridgingRelease(kCTRubyAnnotationAttributeName) value:CFBridgingRelease(rubyAnnotation) range:NSMakeRange(baseRange.location + i, 1)];
+      }
+      [self deleteCharactersInRange:[result rangeAtIndex:3]];
+      [self deleteCharactersInRange:[result rangeAtIndex:1]];
+      offset -= [result rangeAtIndex:3].length + [result rangeAtIndex:1].length;
+    } else {
+      NSFont *rubyFont = [self attribute:NSFontAttributeName atIndex:[result rangeAtIndex:5].location effectiveRange:NULL];
+      rubyFont = [[NSFontManager sharedFontManager] convertFont:rubyFont toSize:[rubyFont pointSize] / 2];
+      [self superscriptRange:[result rangeAtIndex:5]];
+      [self addAttribute:NSFontAttributeName value:rubyFont range:[result rangeAtIndex:5]];
+      [self addAttribute:NSBaselineOffsetAttributeName value:@(rubyFont.ascender) range:[result rangeAtIndex:5]];
+      [self deleteCharactersInRange:[result rangeAtIndex:6]];
+      [self deleteCharactersInRange:[result rangeAtIndex:4]];
+      [self deleteCharactersInRange:[result rangeAtIndex:1]];
+      offset -= [result rangeAtIndex:6].length + [result rangeAtIndex:4].length + [result rangeAtIndex:1].length;
+    }
+  }];
+}
+
 @end
 
 static const CGFloat kOffsetHeight = 5;
@@ -404,23 +444,23 @@ - (void)         setAttrs:(NSDictionary *)attrs
     }
 
     NSMutableDictionary *symbolAttrsBackFill = [symbolAttrs mutableCopy];
-    symbolAttrsBackFill[NSGlyphInfoAttributeName] =
-      [NSGlyphInfo glyphInfoWithGlyphName:@"gid4966" forFont:symbolFont baseString:@"◀"];
-    _symbolBackFill = [[NSAttributedString alloc] initWithString:@"◀" attributes:symbolAttrsBackFill];
-
     NSMutableDictionary *symbolAttrsBackStroke = [symbolAttrs mutableCopy];
-    symbolAttrsBackStroke[NSGlyphInfoAttributeName] =
-      [NSGlyphInfo glyphInfoWithGlyphName:@"gid4969" forFont:symbolFont baseString:@"◁"];
-    _symbolBackStroke = [[NSAttributedString alloc] initWithString:@"◁" attributes:symbolAttrsBackStroke];
-
     NSMutableDictionary *symbolAttrsForwardFill = [symbolAttrs mutableCopy];
-    symbolAttrsForwardFill[NSGlyphInfoAttributeName] =
-      [NSGlyphInfo glyphInfoWithGlyphName:@"gid4967" forFont:symbolFont baseString:@"▶"];
-    _symbolForwardFill = [[NSAttributedString alloc] initWithString:@"▶" attributes:symbolAttrsForwardFill];
-
     NSMutableDictionary *symbolAttrsForwardStroke = [symbolAttrs mutableCopy];
-    symbolAttrsForwardStroke[NSGlyphInfoAttributeName] =
-      [NSGlyphInfo glyphInfoWithGlyphName:@"gid4968" forFont:symbolFont baseString:@"▷"];
+    if (@available(macOS 10.13, *)) {
+      symbolAttrsBackFill[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithCGGlyph:0xE92 forFont:symbolFont baseString:@"◀"];
+      symbolAttrsBackStroke[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithCGGlyph:0xE95 forFont:symbolFont baseString:@"◁"];
+      symbolAttrsForwardFill[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithCGGlyph:0xE93 forFont:symbolFont baseString:@"▶"];
+      symbolAttrsForwardStroke[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithCGGlyph:0xE94 forFont:symbolFont baseString:@"▷"];
+    } else {
+      symbolAttrsBackFill[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithGlyphName:@"gid4966" forFont:symbolFont baseString:@"◀"];
+      symbolAttrsBackStroke[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithGlyphName:@"gid4969" forFont:symbolFont baseString:@"◁"];
+      symbolAttrsForwardFill[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithGlyphName:@"gid4967" forFont:symbolFont baseString:@"▶"];
+      symbolAttrsForwardStroke[NSGlyphInfoAttributeName] = [NSGlyphInfo glyphInfoWithGlyphName:@"gid4968" forFont:symbolFont baseString:@"▷"];
+    }
+    _symbolBackFill = [[NSAttributedString alloc] initWithString:@"◀" attributes:symbolAttrsBackFill];
+    _symbolBackStroke = [[NSAttributedString alloc] initWithString:@"◁" attributes:symbolAttrsBackStroke];
+    _symbolForwardFill = [[NSAttributedString alloc] initWithString:@"▶" attributes:symbolAttrsForwardFill];
     _symbolForwardStroke = [[NSAttributedString alloc] initWithString:@"▷" attributes:symbolAttrsForwardStroke];
   }
 }
@@ -2041,6 +2081,7 @@ - (void)showPreedit:(NSString *)preedit
     }
 
     [item formatMarkDown];
+    [item annotateRubyInVerticalLayout:theme.vertical];
     if (!theme.linear) {
       paragraphStyleCandidate = [theme.paragraphStyle mutableCopy];
       paragraphStyleCandidate.headIndent = labelWidth;
@@ -2152,8 +2193,10 @@ - (void)showPreedit:(NSString *)preedit
   }
   if (numCandidates > 0) {
     NSRange candidateBlockRange = NSMakeRange(candidateBlockStart, (!theme.linear && pagingRange.length > 0 ? pagingRange.location : text.length) - candidateBlockStart);
+    NSFont *refFont = getHighestFont(@[theme.attrs[NSFontAttributeName], theme.labelAttrs[NSFontAttributeName],
+                                       theme.commentAttrs[NSFontAttributeName]], theme.vertical);
     [self setLayoutForRange:candidateBlockRange
-          withReferenceFont:(theme.vertical ? [theme.attrs[NSFontAttributeName] verticalFont] : theme.attrs[NSFontAttributeName])
+          withReferenceFont:(theme.vertical ? refFont.verticalFont : refFont)
              paragraphStyle:theme.paragraphStyle];
     if (!theme.linear && pagingRange.length > 0) {
       [self setLayoutForRange:pagingRange
@@ -2302,6 +2345,19 @@ static CGFloat getLineHeight(NSFont *font, BOOL vertical) {
   return lineHeight;
 }
 
+static NSFont * getHighestFont(NSArray<NSFont *>*fonts, BOOL vertical) {
+  NSFont *highestFont;
+  CGFloat maxHeight = 0.0;
+  for (NSFont *font in fonts) {
+    CGFloat fontHeight = getLineHeight(font, vertical);
+    if (fontHeight > maxHeight) {
+      highestFont = font;
+      maxHeight = fontHeight;
+    }
+  }
+  return highestFont;
+}
+
 static void updateCandidateListLayout(BOOL *isLinearCandidateList, BOOL *isTabledCandidateList, SquirrelConfig *config, NSString *prefix) {
   NSString *candidateListLayout = [config getString:[prefix stringByAppendingString:@"/candidate_list_layout"]];
   if ([candidateListLayout isEqualToString:@"stacked"]) {