diff --git a/conf/lex.go b/conf/lex.go
index 013b883866..f9920a4411 100644
--- a/conf/lex.go
+++ b/conf/lex.go
@@ -263,7 +263,8 @@ func lexTop(lx *lexer) stateFn {
 
 	switch r {
 	case topOptStart:
-		return lexSkip(lx, lexTop)
+		lx.push(lexTop)
+		return lexSkip(lx, lexBlockStart)
 	case commentHashStart:
 		lx.push(lexTop)
 		return lexCommentStart
@@ -318,6 +319,71 @@ func lexTopValueEnd(lx *lexer) stateFn {
 		"comment or EOF, but got '%v' instead.", r)
 }
 
+func lexBlockStart(lx *lexer) stateFn {
+	r := lx.next()
+	if unicode.IsSpace(r) {
+		return lexSkip(lx, lexBlockStart)
+	}
+
+	switch r {
+	case topOptStart:
+		lx.push(lexBlockEnd)
+		return lexSkip(lx, lexBlockStart)
+	case commentHashStart:
+		lx.push(lexBlockEnd)
+		return lexCommentStart
+	case commentSlashStart:
+		rn := lx.next()
+		if rn == commentSlashStart {
+			lx.push(lexBlockEnd)
+			return lexCommentStart
+		}
+		lx.backup()
+		fallthrough
+	case eof:
+		if lx.pos > lx.start {
+			return lx.errorf("Unexpected EOF.")
+		}
+		lx.emit(itemEOF)
+		return nil
+	}
+
+	// At this point, the only valid item can be a key, so we back up
+	// and let the key lexer do the rest.
+	lx.backup()
+	lx.push(lexBlockEnd)
+	return lexKeyStart
+}
+
+// lexBlockEnd is entered whenever a block-level value has been consumed.
+// It must see only whitespace, and will turn back to lexTop upon a "}".
+func lexBlockEnd(lx *lexer) stateFn {
+	r := lx.next()
+	switch {
+	case r == commentHashStart:
+		// a comment will read to a new line for us.
+		lx.push(lexBlockEnd)
+		return lexCommentStart
+	case r == commentSlashStart:
+		rn := lx.next()
+		if rn == commentSlashStart {
+			lx.push(lexBlockEnd)
+			return lexCommentStart
+		}
+		lx.backup()
+		fallthrough
+	case isNL(r) || isWhitespace(r):
+		return lexBlockEnd
+	case r == optValTerm || r == topOptValTerm:
+		lx.ignore()
+		return lexBlockStart
+	case r == topOptTerm:
+		lx.ignore()
+		return lx.pop()
+	}
+	return lx.errorf("Expected a block-level value to end with a '}', but got '%v' instead.", r)
+}
+
 // lexKeyStart consumes a key name up until the first non-whitespace character.
 // lexKeyStart will ignore whitespace. It will also eat enclosing quotes.
 func lexKeyStart(lx *lexer) stateFn {
diff --git a/conf/parse_test.go b/conf/parse_test.go
index 8cf1ea98f3..98dffc0ab2 100644
--- a/conf/parse_test.go
+++ b/conf/parse_test.go
@@ -740,3 +740,78 @@ func TestJSONParseCompat(t *testing.T) {
 		})
 	}
 }
+
+func TestBlocks(t *testing.T) {
+	for _, test := range []struct {
+		name     string
+		input    string
+		expected map[string]any
+		err      string
+		linepos  string
+	}{
+		{
+			"inline block",
+			`{ listen: 0.0.0.0:4222 }`,
+			map[string]any{
+				"listen": "0.0.0.0:4222",
+			},
+			"", "",
+		},
+		{
+			"newline block",
+			`{
+				listen: 0.0.0.0:4222
+			 }`,
+			map[string]any{
+				"listen": "0.0.0.0:4222",
+			},
+			"", "",
+		},
+		{
+			"newline block with trailing comment",
+			`
+			{
+				listen: 0.0.0.0:4222
+			}
+			# wibble
+			`,
+			map[string]any{
+				"listen": "0.0.0.0:4222",
+			},
+			"", "",
+		},
+		{
+			"nested newline blocks with trailing comment",
+			`
+			{
+				{
+					listen: 0.0.0.0:4222 // random comment
+				}
+				# wibble1
+			}
+			# wibble2
+			`,
+			map[string]any{
+				"listen": "0.0.0.0:4222",
+			},
+			"", "",
+		},
+	} {
+		t.Run(test.name, func(t *testing.T) {
+			f, err := os.CreateTemp(t.TempDir(), "nats.conf-")
+			if err != nil {
+				t.Fatal(err)
+			}
+			if err := os.WriteFile(f.Name(), []byte(test.input), 066); err != nil {
+				t.Error(err)
+			}
+			if m, err := ParseFile(f.Name()); err == nil {
+				if !reflect.DeepEqual(m, test.expected) {
+					t.Fatalf("Not Equal:\nReceived: '%+v'\nExpected: '%+v'\n", m, test.expected)
+				}
+			} else if !strings.Contains(err.Error(), test.err) || !strings.Contains(err.Error(), test.linepos) {
+				t.Errorf("expected invalid conf error, got: %v", err)
+			}
+		})
+	}
+}
diff --git a/server/server_test.go b/server/server_test.go
index b75c48badd..3dae1aa55e 100644
--- a/server/server_test.go
+++ b/server/server_test.go
@@ -2121,3 +2121,21 @@ func TestServerAuthBlockAndSysAccounts(t *testing.T) {
 	_, err = nats.Connect(s.ClientURL())
 	require_Error(t, err, nats.ErrAuthorization, errors.New("nats: Authorization Violation"))
 }
+
+// https://github.com/nats-io/nats-server/issues/5396
+func TestServerConfigLastLineComments(t *testing.T) {
+	conf := createConfFile(t, []byte(`
+	{
+		"listen":  "0.0.0.0:4222"
+	}
+	# wibble
+	`))
+
+	s, _ := RunServerWithConfig(conf)
+	defer s.Shutdown()
+
+	// This should work of course.
+	nc, err := nats.Connect(s.ClientURL())
+	require_NoError(t, err)
+	defer nc.Close()
+}