diff --git a/.changeset/eight-teachers-sniff.md b/.changeset/eight-teachers-sniff.md
new file mode 100644
index 000000000..ac6b9ae77
--- /dev/null
+++ b/.changeset/eight-teachers-sniff.md
@@ -0,0 +1,5 @@
+---
+'@astrojs/compiler': patch
+---
+
+Properly handle nested expressions that return multiple elements
diff --git a/internal/printer/printer_test.go b/internal/printer/printer_test.go
index ac3cde831..c3c5cd02a 100644
--- a/internal/printer/printer_test.go
+++ b/internal/printer/printer_test.go
@@ -619,6 +619,27 @@ const groups = [[0, 1, 2], [3, 4, 5]];
 				code: `${$$maybeRenderHead($$result)}<article>${(previous || next) && $$render` + BACKTICK + `<aside>${previous && $$render` + BACKTICK + `<div>Previous Article: <a rel="prev"${$$addAttribute(new URL(previous.link, Astro.site).pathname, "href")}>${previous.text}</a></div>` + BACKTICK + `}${next && $$render` + BACKTICK + `<div>Next Article: <a rel="next"${$$addAttribute(new URL(next.link, Astro.site).pathname, "href")}>${next.text}</a></div>` + BACKTICK + `}</aside>` + BACKTICK + `}</article>`,
 			},
 		},
+		{
+			name:   "nested expressions II",
+			source: `<article>{(previous || next) && <aside>{previous && <div>Previous Article: <a rel="prev" href={new URL(previous.link, Astro.site).pathname}>{previous.text}</a></div>} {next && <div>Next Article: <a rel="next" href={new URL(next.link, Astro.site).pathname}>{next.text}</a></div>}</aside>}</article>`,
+			want: want{
+				code: `${$$maybeRenderHead($$result)}<article>${(previous || next) && $$render` + BACKTICK + `<aside>${previous && $$render` + BACKTICK + `<div>Previous Article: <a rel="prev"${$$addAttribute(new URL(previous.link, Astro.site).pathname, "href")}>${previous.text}</a></div>` + BACKTICK + `} ${next && $$render` + BACKTICK + `<div>Next Article: <a rel="next"${$$addAttribute(new URL(next.link, Astro.site).pathname, "href")}>${next.text}</a></div>` + BACKTICK + `}</aside>` + BACKTICK + `}</article>`,
+			},
+		},
+		{
+			name:   "nested expressions III",
+			source: `<div>{x.map((x) => x ? <div>{true ? <span>{x}</span> : null}</div> : <div>{false ? null : <span>{x}</span>}</div>)}</div>`,
+			want: want{
+				code: "${$$maybeRenderHead($$result)}<div>${x.map((x) => x ? $$render`<div>${true ? $$render`<span>${x}</span>` : null}</div>` : $$render`<div>${false ? null : $$render`<span>${x}</span>`}</div>`)}</div>",
+			},
+		},
+		{
+			name:   "nested expressions IV",
+			source: `<div>{() => { if (value > 0.25) { return <span>Default</span> } else if (value > 0.5) { return <span>Another</span> } else if (value > 0.75) { return <span>Other</span> } return <span>Yet Other</span> }}</div>`,
+			want: want{
+				code: "${$$maybeRenderHead($$result)}<div>${() => { if (value > 0.25) { return $$render`<span>Default</span>`} else if (value > 0.5) { return $$render`<span>Another</span>`} else if (value > 0.75) { return $$render`<span>Other</span>`} return $$render`<span>Yet Other</span>`}}</div>",
+			},
+		},
 		{
 			name: "expressions with JS comments",
 			source: `---
diff --git a/internal/token.go b/internal/token.go
index 8bfe7b4dc..15cf0d20e 100644
--- a/internal/token.go
+++ b/internal/token.go
@@ -250,6 +250,7 @@ type Tokenizer struct {
 	// tt is the TokenType of the current token.
 	tt            TokenType
 	prevTokenType TokenType
+	prevTokens    []Token
 	fm            FrontmatterState
 	m             MarkdownState
 	// err is the first error encountered during tokenization. It is possible
@@ -1331,23 +1332,51 @@ func (z *Tokenizer) isAtExpressionBoundary() bool {
 	return true
 }
 
+func (z *Tokenizer) trackPreviousTokens() {
+	// Reset stack on expression boundaries
+	if z.tt == StartExpressionToken || z.tt == EndExpressionToken {
+		z.prevTokens = make([]Token, 0)
+	}
+	if z.tt == StartTagToken {
+		z.prevTokens = append(z.prevTokens, z.Token())
+	} else if z.tt == EndTagToken {
+		if len(z.prevTokens) > 0 {
+			// This is a very simple stack that pops matching closing elements off the stack,
+			// which is good enough for our purposes.
+			// We only use this to track when `{` should be `StartExpressionToken` or `TextToken`
+			for i := 1; i < len(z.prevTokens)+1; i++ {
+				tok := z.prevTokens[len(z.prevTokens)-i]
+				if tok.Data == string(z.buf[z.data.Start:z.data.End]) {
+					if len(z.prevTokens) == 1 {
+						z.prevTokens = make([]Token, 0)
+					} else {
+						z.prevTokens = z.prevTokens[0:i]
+						z.prevTokens = append(z.prevTokens, z.prevTokens[i:]...)
+					}
+				}
+			}
+		}
+	}
+}
+
 // Next scans the next token and returns its type.
 func (z *Tokenizer) Next() TokenType {
+	z.trackPreviousTokens()
 	z.raw.Start = z.raw.End
 	z.data.Start = z.raw.End
 	z.data.End = z.raw.End
 	z.prevTokenType = z.tt
 
-	// This handles expressions nested inside of Frontmatter elements
-	// but preserves `{}` as text outside of elements
-	if z.fm == FrontmatterOpen {
+	// Properly handle multiple nested expressions
+	if len(z.expressionStack) > 0 && len(z.prevTokens) == 0 {
 		tt := z.Token().Type
 		switch tt {
-		case StartTagToken, EndTagToken:
+		case StartTagToken, EndExpressionToken, TextToken:
 		default:
 			z.openBraceIsExpressionStart = false
 		}
 	}
+
 	if z.rawTag != "" {
 		if z.rawTag == "plaintext" {
 			// Read everything up to EOF.
diff --git a/internal/token_test.go b/internal/token_test.go
index 1a5e035a5..1f1cd8f03 100644
--- a/internal/token_test.go
+++ b/internal/token_test.go
@@ -198,6 +198,20 @@ func TestBasic(t *testing.T) {
 		}}</div>`,
 			[]TokenType{StartTagToken, StartExpressionToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, TextToken, EndExpressionToken, EndTagToken},
 		},
+		{
+			"expression with multiple elements",
+			`<div>{() => {
+				if (value > 0.25) {
+					return <span>Default</span>
+				} else if (value > 0.5) {
+					return <span>Another</span>
+				} else if (value > 0.75) {
+					return <span>Other</span>
+				}
+				return <span>Yet Other</span>
+			}}</div>`,
+			[]TokenType{StartTagToken, StartExpressionToken, TextToken, TextToken, TextToken, TextToken, TextToken, StartTagToken, TextToken, EndTagToken, TextToken, TextToken, TextToken, TextToken, StartTagToken, TextToken, EndTagToken, TextToken, TextToken, TextToken, TextToken, StartTagToken, TextToken, EndTagToken, TextToken, TextToken, StartTagToken, TextToken, EndTagToken, TextToken, TextToken, EndExpressionToken, EndTagToken},
+		},
 		{
 			"attribute expression with quoted braces",
 			`<div value={"{"} />`,