diff --git a/caddyconfig/caddyfile/dispenser.go b/caddyconfig/caddyfile/dispenser.go
index fbe71ad02ff..8a78f4337d9 100755
--- a/caddyconfig/caddyfile/dispenser.go
+++ b/caddyconfig/caddyfile/dispenser.go
@@ -458,6 +458,60 @@ func (d *Dispenser) isNewLine() bool {
 	if d.cursor > len(d.tokens)-1 {
 		return false
 	}
-	return d.tokens[d.cursor-1].File != d.tokens[d.cursor].File ||
-		d.tokens[d.cursor-1].Line+d.numLineBreaks(d.cursor-1) < d.tokens[d.cursor].Line
+
+	prev := d.tokens[d.cursor-1]
+	curr := d.tokens[d.cursor]
+
+	// If the previous token is from a different file,
+	// we can assume it's from a different line
+	if prev.File != curr.File {
+		return true
+	}
+
+	// The previous token may contain line breaks if
+	// it was quoted and spanned multiple lines. e.g:
+	//
+	// dir "foo
+	//   bar
+	//   baz"
+	prevLineBreaks := d.numLineBreaks(d.cursor - 1)
+
+	// If the previous token (incl line breaks) ends
+	// on a line earlier than the current token,
+	// then the current token is on a new line
+	return prev.Line+prevLineBreaks < curr.Line
+}
+
+// isNextOnNewLine determines whether the current token is on a different
+// line (higher line number) than the next token. It handles imported
+// tokens correctly. If there isn't a next token, it returns true.
+func (d *Dispenser) isNextOnNewLine() bool {
+	if d.cursor < 0 {
+		return false
+	}
+	if d.cursor >= len(d.tokens)-1 {
+		return true
+	}
+
+	curr := d.tokens[d.cursor]
+	next := d.tokens[d.cursor+1]
+
+	// If the next token is from a different file,
+	// we can assume it's from a different line
+	if curr.File != next.File {
+		return true
+	}
+
+	// The current token may contain line breaks if
+	// it was quoted and spanned multiple lines. e.g:
+	//
+	// dir "foo
+	//   bar
+	//   baz"
+	currLineBreaks := d.numLineBreaks(d.cursor)
+
+	// If the current token (incl line breaks) ends
+	// on a line earlier than the next token,
+	// then the next token is on a new line
+	return curr.Line+currLineBreaks < next.Line
 }
diff --git a/caddyconfig/caddyfile/parse.go b/caddyconfig/caddyfile/parse.go
index 1e694f9f52e..b4632384815 100755
--- a/caddyconfig/caddyfile/parse.go
+++ b/caddyconfig/caddyfile/parse.go
@@ -494,6 +494,13 @@ func (p *parser) directive() error {
 	for p.Next() {
 		if p.Val() == "{" {
 			p.nesting++
+			if !p.isNextOnNewLine() && p.Token().wasQuoted == 0 {
+				return p.Err("Unexpected next token after '{' on same line")
+			}
+		} else if p.Val() == "{}" {
+			if p.isNextOnNewLine() && p.Token().wasQuoted == 0 {
+				return p.Err("Unexpected '{}' at end of line")
+			}
 		} else if p.isNewLine() && p.nesting == 0 {
 			p.cursor-- // read too far
 			break
diff --git a/caddyconfig/caddyfile/parse_test.go b/caddyconfig/caddyfile/parse_test.go
index 8d43e1aa536..c3f6fa644b9 100755
--- a/caddyconfig/caddyfile/parse_test.go
+++ b/caddyconfig/caddyfile/parse_test.go
@@ -191,6 +191,20 @@ func TestParseOneAndImport(t *testing.T) {
 
 		{``, false, []string{}, []int{}},
 
+		// Unexpected next token after '{' on same line
+		{`localhost
+		  dir1 { a b }`, true, []string{"localhost"}, []int{}},
+		// Workaround with quotes
+		{`localhost
+		  dir1 "{" a b "}"`, false, []string{"localhost"}, []int{5}},
+
+		// Unexpected '{}' at end of line
+		{`localhost
+		  dir1 {}`, true, []string{"localhost"}, []int{}},
+		// Workaround with quotes
+		{`localhost
+		  dir1 "{}"`, false, []string{"localhost"}, []int{2}},
+
 		// import with args
 		{`import testdata/import_args0.txt a`, false, []string{"a"}, []int{}},
 		{`import testdata/import_args1.txt a b`, false, []string{"a", "b"}, []int{}},