diff --git a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-execution/src/test/java/org/finos/legend/engine/plan/execution/stores/relational/test/semiStructured/TestSnowflakeSemiStructuredMatching.java b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-execution/src/test/java/org/finos/legend/engine/plan/execution/stores/relational/test/semiStructured/TestSnowflakeSemiStructuredMatching.java
index 93645d33e31..35e5cf33790 100644
--- a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-execution/src/test/java/org/finos/legend/engine/plan/execution/stores/relational/test/semiStructured/TestSnowflakeSemiStructuredMatching.java
+++ b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-execution/src/test/java/org/finos/legend/engine/plan/execution/stores/relational/test/semiStructured/TestSnowflakeSemiStructuredMatching.java
@@ -115,7 +115,7 @@ public void testSemiStructuredMatchWithVariableAccess()
                 "        (\n" +
                 "          type = TDS[(Max Amount Flag, Boolean, \"\", \"\")]\n" +
                 "          resultColumns = [(\"Max Amount Flag\", \"\")]\n" +
-                "          sql = select case when \"root\".CUSTOMER['transactionDetails']['payment']['@type']::varchar in ('CashOnDeliveryPayment') then case when \"root\".CUSTOMER['transactionDetails']['payment']['amountToBePaid'] < ${maxAmount} then 'true' else 'false' end when \"root\".CUSTOMER['transactionDetails']['payment']['@type']::varchar in ('PrepaidPayment', 'WalletPrepaidPayment', 'CardPrepaidPayment') then case when \"root\".CUSTOMER['transactionDetails']['payment']['amountPaid'] < ${maxAmount} then 'true' else 'false' end else null end as \"Max Amount Flag\" from ORDER_SCHEMA.ORDER_TABLE as \"root\"\n" +
+                "          sql = select case when \"root\".CUSTOMER['transactionDetails']['payment']['@type']::varchar in ('CashOnDeliveryPayment') then case when \"root\".CUSTOMER['transactionDetails']['payment']['amountToBePaid'] < ${maxAmount} then true else false end when \"root\".CUSTOMER['transactionDetails']['payment']['@type']::varchar in ('PrepaidPayment', 'WalletPrepaidPayment', 'CardPrepaidPayment') then case when \"root\".CUSTOMER['transactionDetails']['payment']['amountPaid'] < ${maxAmount} then true else false end else null end as \"Max Amount Flag\" from ORDER_SCHEMA.ORDER_TABLE as \"root\"\n" +
                 "          connection = RelationalDatabaseConnection(type = \"Snowflake\")\n" +
                 "        )\n" +
                 "      ) \n" +
diff --git a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/executionPlan/tests/executionPlanTestSnowflake.pure b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/executionPlan/tests/executionPlanTestSnowflake.pure
index f9a79437922..f0487a9aef8 100644
--- a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/executionPlan/tests/executionPlanTestSnowflake.pure
+++ b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/executionPlan/tests/executionPlanTestSnowflake.pure
@@ -53,7 +53,7 @@ import meta::pure::functions::collection::*;
 function <<test.Test>> meta::pure::executionPlan::tests::snowflake::testFilterEqualsWithOptionalParameter_Snowflake():Boolean[1]
 {
    let generatedPlan = executionPlan({optionalID: String[0..1], optionalActive: Boolean[0..1]|Interaction.all()->filter(i|$i.id==$optionalID && $i.active==$optionalActive)->project(col(i|$i.time, 'Time'))}, simpleRelationalMapping, ^Runtime(connectionStores=^ConnectionStore(element = relationalDB,connection=meta::pure::executionPlan::tests::snowflake::relationalConnectionForSnowflake(true))), meta::relational::extension::relationalExtensions());
-   let expectedPlan = 'RelationalBlockExecutionNode(type=TDS[(Time,Integer,INT,"")](FunctionParametersValidationNode(functionParameters=[optionalID:String[0..1],optionalActive:Boolean[0..1]])SQL(type=VoidresultColumns=[]sql=ALTERSESSIONSETQUERY_TAG=\'{"executionTraceID":"${execID}","engineUser":"${userId}","referer":"${referer}"}\';connection=RelationalDatabaseConnection(type="Snowflake"))Relational(type=TDS[(Time,Integer,INT,"")]resultColumns=[("Time",INT)]sql=select"root".timeas"Time"frominteractionTableas"root"where((${optionalVarPlaceHolderOperationSelector(optionalID![],\'"root".ID=${varPlaceHolderToString(optionalID![]"\\\'""\\\'"{"\\\'":"\\\'\\\'"}"null")}\',\'"root".IDisnull\')})and(${optionalVarPlaceHolderOperationSelector(optionalActive![],\'casewhen"root".active=\\\'Y\\\'then\\\'true\\\'else\\\'false\\\'end=${varPlaceHolderToString(optionalActive![]"\\\'""\\\'"{}"null")}\',\'casewhen"root".active=\\\'Y\\\'then\\\'true\\\'else\\\'false\\\'endisnull\')}))connection=RelationalDatabaseConnection(type="Snowflake")))finallyExecutionNodes=(SQL(type=VoidresultColumns=[]sql=ALTERSESSIONUNSETQUERY_TAG;connection=RelationalDatabaseConnection(type="Snowflake"))))';
+   let expectedPlan = 'RelationalBlockExecutionNode(type=TDS[(Time,Integer,INT,"")](FunctionParametersValidationNode(functionParameters=[optionalID:String[0..1],optionalActive:Boolean[0..1]])SQL(type=VoidresultColumns=[]sql=ALTERSESSIONSETQUERY_TAG=\'{"executionTraceID":"${execID}","engineUser":"${userId}","referer":"${referer}"}\';connection=RelationalDatabaseConnection(type="Snowflake"))Relational(type=TDS[(Time,Integer,INT,"")]resultColumns=[("Time",INT)]sql=select"root".timeas"Time"frominteractionTableas"root"where((${optionalVarPlaceHolderOperationSelector(optionalID![],\'"root".ID=${varPlaceHolderToString(optionalID![]"\\\'""\\\'"{"\\\'":"\\\'\\\'"}"null")}\',\'"root".IDisnull\')})and(${optionalVarPlaceHolderOperationSelector(optionalActive![],\'casewhen"root".active=\\\'Y\\\'then\\\'true\\\'else\\\'false\\\'end=${varPlaceHolderToString(optionalActive![]""""{}"null")}\',\'casewhen"root".active=\\\'Y\\\'then\\\'true\\\'else\\\'false\\\'endisnull\')}))connection=RelationalDatabaseConnection(type="Snowflake")))finallyExecutionNodes=(SQL(type=VoidresultColumns=[]sql=ALTERSESSIONUNSETQUERY_TAG;connection=RelationalDatabaseConnection(type="Snowflake"))))';
    assertEquals($expectedPlan, $generatedPlan->planToStringWithoutFormatting(meta::relational::extension::relationalExtensions()));
    assertSameElements(templateFunctionsList(),$generatedPlan.processingTemplateFunctions);
 }
diff --git a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/sqlQueryToString/snowflakeExtension.pure b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/sqlQueryToString/snowflakeExtension.pure
index f8080beafdc..f2fb47dbcdf 100644
--- a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/sqlQueryToString/snowflakeExtension.pure
+++ b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/sqlQueryToString/snowflakeExtension.pure
@@ -51,7 +51,8 @@ function <<access.private>> meta::relational::functions::sqlQueryToString::snowf
    newMap([
       pair(StrictDate, ^LiteralProcessor(format = '\'%s\'::date', transform = {d:StrictDate[1], dbTimeZone:String[0..1] | $d->convertDateToSqlString($dbTimeZone)})),
       pair(DateTime,   ^LiteralProcessor(format = '\'%s\'::timestamp', transform = {d:DateTime[1], dbTimeZone:String[0..1] | $d->convertDateToSqlString($dbTimeZone)})),
-      pair(Date,       ^LiteralProcessor(format = '\'%s\'::timestamp', transform = {d:Date[1], dbTimeZone:String[0..1] | $d->convertDateToSqlString($dbTimeZone)}))
+      pair(Date,       ^LiteralProcessor(format = '\'%s\'::timestamp', transform = {d:Date[1], dbTimeZone:String[0..1] | $d->convertDateToSqlString($dbTimeZone)})),
+      pair(Boolean,    ^LiteralProcessor(format = '%s', transform = toString_Any_1__String_1_->literalTransform()))
    ])
 }
 
diff --git a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/tests/testSnowflakeWithFunction.pure b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/tests/testSnowflakeWithFunction.pure
index e4d20b8279f..79fe5a4d855 100644
--- a/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/tests/testSnowflakeWithFunction.pure
+++ b/legend-engine-xts-relationalStore/legend-engine-xt-relationalStore-dbExtension/legend-engine-xt-relationalStore-snowflake/legend-engine-xt-relationalStore-snowflake-pure/src/main/resources/core_relational_snowflake/relational/tests/testSnowflakeWithFunction.pure
@@ -38,3 +38,14 @@ function <<test.Test>> meta::relational::tests::query::snowflake::testFilterUsin
    let s = toSQLString($fn, simpleRelationalMapping, meta::relational::runtime::DatabaseType.Snowflake, meta::relational::extension::relationalExtensions());
    assertEquals('select "root".ID as "pk_0", "root".FIRSTNAME as "firstName", "root".AGE as "age", "root".LASTNAME as "lastName" from personTable as "root" left outer join firmTable as "firmTable_d#2_dy0_d#3_d_m1" on ("firmTable_d#2_dy0_d#3_d_m1".ID = "root".FIRMID) where "firmTable_d#2_dy0_d#3_d_m1".LEGALNAME regexp \'^[A-Za-z0-9]*$\'',$s);
 }
+
+function <<test.Test>> meta::relational::tests::query::snowflake::testFilterBoolean():Boolean[1]
+{
+   let sql =toSQLString(|Person.all()->project(p|$p.firstName,'firstName')->filter(p | if(
+      $p.getString('firstName')->startsWith('d'),
+      |true,
+      |false
+    )),
+      simpleRelationalMapping, meta::relational::runtime::DatabaseType.Snowflake, meta::relational::extension::relationalExtensions());
+   assertEquals('select "root".FIRSTNAME as "firstName" from personTable as "root" where case when "root".FIRSTNAME like \'d%\' then true else false end', $sql);
+}
\ No newline at end of file