diff --git a/ballerina/Dependencies.toml b/ballerina/Dependencies.toml
index 61b14bc..15a6530 100644
--- a/ballerina/Dependencies.toml
+++ b/ballerina/Dependencies.toml
@@ -73,6 +73,17 @@ org = "ballerina"
 name = "lang.object"
 version = "0.0.0"
 
+[[package]]
+org = "ballerina"
+name = "lang.regexp"
+version = "0.0.0"
+dependencies = [
+	{org = "ballerina", name = "jballerina.java"}
+]
+modules = [
+	{org = "ballerina", packageName = "lang.regexp", moduleName = "lang.regexp"}
+]
+
 [[package]]
 org = "ballerina"
 name = "lang.value"
@@ -141,6 +152,7 @@ dependencies = [
 	{org = "ballerina", name = "file"},
 	{org = "ballerina", name = "io"},
 	{org = "ballerina", name = "lang.array"},
+	{org = "ballerina", name = "lang.regexp"},
 	{org = "ballerina", name = "log"},
 	{org = "ballerina", name = "test"}
 ]
diff --git a/ballerina/modules/lexer/lexer.bal b/ballerina/modules/lexer/lexer.bal
index d0d454f..cc27183 100644
--- a/ballerina/modules/lexer/lexer.bal
+++ b/ballerina/modules/lexer/lexer.bal
@@ -62,7 +62,7 @@ public isolated function scan(LexerState state) returns LexerState|LexicalError
         return state.index == 0 ? state.tokenize(EMPTY_LINE) : state.tokenize(EOL);
     }
 
-    // Check for line breaks when reading form string
+    // Check for line breaks when reading from string
     if state.peek() == "\n" && state.context != LEXER_DOUBLE_QUOTE {
         state.isNewLine = true;
         return state.tokenize(EOL);
diff --git a/ballerina/modules/parser/parser.bal b/ballerina/modules/parser/parser.bal
index f2aba6b..2a70997 100644
--- a/ballerina/modules/parser/parser.bal
+++ b/ballerina/modules/parser/parser.bal
@@ -244,3 +244,18 @@ public isolated function parse(ParserState state, ParserOption option = DEFAULT,
 
     return generateGrammarError(state, string `Invalid token '${state.currentToken.token}' as the first for generating an event`);
 }
+
+# Check if the given string is a valid planar scalar.
+#
+# + value - The string to be checked
+# + return - True if the string is a valid planar scalar. Else, false.
+public isolated function isValidPlanarScalar(string value) returns boolean {
+    string? planarScalarResult = ();
+    do {   
+        ParserState parserState = check new ([value]);
+        planarScalarResult = check planarScalar(parserState, false);
+    } on fail {
+        return false;
+    }
+    return planarScalarResult is string && planarScalarResult.trim() == value.trim();
+}
diff --git a/ballerina/modules/parser/scalar.bal b/ballerina/modules/parser/scalar.bal
index 511bfd2..2e99faf 100644
--- a/ballerina/modules/parser/scalar.bal
+++ b/ballerina/modules/parser/scalar.bal
@@ -169,14 +169,15 @@ isolated function singleQuoteScalar(ParserState state) returns ParsingError|stri
 
 # Parse the string of a planar scalar.
 #
-# + state - Current parser state
+# + state - Current parser state  
+# + allowTokensAsPlanar - If set, then the restricted tokens are allowed as planar scalar
 # + return - Parsed planar scalar value
-isolated function planarScalar(ParserState state) returns ParsingError|string {
+isolated function planarScalar(ParserState state, boolean allowTokensAsPlanar = true) returns ParsingError|string {
     // Process the first planar char
     string lexemeBuffer = state.currentToken.value;
     boolean isFirstLine = true;
     string newLineBuffer = "";
-    state.lexerState.allowTokensAsPlanar = true;
+    state.lexerState.allowTokensAsPlanar = allowTokensAsPlanar;
 
     check checkToken(state, peek = true);
 
diff --git a/ballerina/modules/serializer/node.bal b/ballerina/modules/serializer/node.bal
index 361e489..e8a3529 100644
--- a/ballerina/modules/serializer/node.bal
+++ b/ballerina/modules/serializer/node.bal
@@ -14,18 +14,17 @@
 
 import yaml.common;
 import yaml.schema;
-
-const string INVALID_PLANAR_PATTERN = "([\\w|\\s]*[\\-|\\?|:|] [\\w|\\s]*)|"
-    + "([\\w|\\s]* #[\\w|\\s]*)|"
-    + "([,|\\[|\\]|\\{|\\}|&\\*|!\\||>|'|\"|%|@|`][\\w|\\s]*)";
+import yaml.parser;
+import ballerina/lang.regexp;
 
 isolated function serializeString(SerializerState state, json data, string tag) {
     string value = data.toString();
-    state.events.push({
-        value: re `${INVALID_PLANAR_PATTERN}`.isFullMatch(value) || state.forceQuotes
-                ? string `${state.delimiter}${value}${state.delimiter}` : value,
-        tag
-    });
+    if value.includes("\n") {
+        value = state.delimiter + regexp:replaceAll(re `\n`, data.toString(), "\\n") + state.delimiter;
+    } else {
+        value = (!parser:isValidPlanarScalar(value) || state.forceQuotes) ? state.delimiter + value + state.delimiter : value;
+    }
+    state.events.push({value, tag});
 }
 
 isolated function serializeSequence(SerializerState state, json[] data, string tag, int depthLevel) returns schema:SchemaError? {
diff --git a/ballerina/modules/serializer/tests/lib_test.bal b/ballerina/modules/serializer/tests/lib_test.bal
index 81d9388..de1ff8e 100644
--- a/ballerina/modules/serializer/tests/lib_test.bal
+++ b/ballerina/modules/serializer/tests/lib_test.bal
@@ -86,14 +86,44 @@ function testQuotesForInvalidPlanarChar(string line) returns error? {
 
 function invalidPlanarDataGen() returns map<[string]> {
     return {
-        "comment": [" #"],
+        "comment": [" # comment"],
         "explicit key": ["? "],
         "sequence entry": ["- "],
         "mapping value": [": "],
-        "flow indicator": ["}a"]
+        "flow indicator": ["}a"],
+        "alias": ["*/*"],
+        "collect-entry": [", "],
+        "anchor": ["&anchor"],
+        "tag": ["!tag"],
+        "directive": ["%YAML 1.2"]
     };
 }
 
+@test:Config {
+    dataProvider: scalarWithNewLinesDataGen,
+    groups: ["serializer"]
+}
+function testScalarWithNewLines(json line, string[] expectedOutputs) returns error? {
+    common:Event[] events = check getSerializedEvents(line);
+    int index = 0;
+    foreach common:Event event in events {
+        if event is common:ScalarEvent {
+            test:assertEquals(event.value, string `"${expectedOutputs[index]}"`);
+            index += 1;
+        }
+    }
+    test:assertEquals(index, expectedOutputs.length());
+}
+
+function scalarWithNewLinesDataGen()returns map<[json, string[]]> =>
+    {
+        "simple scalar": ["first\nsecond", ["first\\nsecond"]],
+        "sequence": [[["first\nsecond"], ["first\nsecond\n\nthird"]], ["first\\nsecond", "first\\nsecond\\n\\nthird"]],
+        "nested sequence": [[[["first\nsecond"]]], ["first\\nsecond"]],
+        "mapping": [{"key\nline": "first\nsecond"}, ["key\\nline", "first\\nsecond"]],
+        "nested mapping": [{"key\nline": {"nested\nline": "first\nsecond"}}, ["key\\nline", "nested\\nline", "first\\nsecond"]]
+    };
+
 @test:Config {
     groups: ["serializer"]
 }