diff --git a/x-pack/plugin/kql/src/test/java/org/elasticsearch/xpack/kql/parser/KqlParserTests.java b/x-pack/plugin/kql/src/test/java/org/elasticsearch/xpack/kql/parser/KqlParserTests.java
index 1c8b1d127e8ed..3b352da0cd88e 100644
--- a/x-pack/plugin/kql/src/test/java/org/elasticsearch/xpack/kql/parser/KqlParserTests.java
+++ b/x-pack/plugin/kql/src/test/java/org/elasticsearch/xpack/kql/parser/KqlParserTests.java
@@ -7,11 +7,21 @@
 
 package org.elasticsearch.xpack.kql.parser;
 
+import org.elasticsearch.core.SuppressForbidden;
 import org.elasticsearch.index.query.MatchAllQueryBuilder;
 import org.elasticsearch.index.query.SearchExecutionContext;
 import org.elasticsearch.test.AbstractBuilderTestCase;
 
+import java.io.BufferedReader;
 import java.io.IOException;
+import java.io.InputStream;
+import java.io.InputStreamReader;
+import java.net.URL;
+import java.net.URLConnection;
+import java.nio.charset.StandardCharsets;
+import java.util.ArrayList;
+import java.util.List;
+import java.util.Objects;
 
 import static org.hamcrest.Matchers.equalTo;
 import static org.hamcrest.Matchers.isA;
@@ -24,6 +34,32 @@ public void testEmptyQueryParsing() throws IOException {
         assertThat(parser.parseKqlQuery("", searchExecutionContext), isA(MatchAllQueryBuilder.class));
     }
 
+    public void testSupportedQueries() throws Exception {
+        KqlParser parser = new KqlParser();
+        SearchExecutionContext searchExecutionContext = createSearchExecutionContext();
+
+        for (String query : readQueries("/supported-queries")) {
+            try {
+                parser.parseKqlQuery(query, searchExecutionContext);
+            } catch (Throwable e) {
+                throw new AssertionError("Unexpected error during query parsing [ " + query + "]", e);
+            }
+        }
+    }
+
+    public void testUnsupportedQueries() throws Exception {
+        KqlParser parser = new KqlParser();
+        SearchExecutionContext searchExecutionContext = createSearchExecutionContext();
+
+        for (String query : readQueries("/unsupported-queries")) {
+            assertThrows(
+                "Was expecting a KqlParsingException exception to be thrown while parsing query [" + query + "]",
+                KqlParsingException.class,
+                () -> parser.parseKqlQuery(query, searchExecutionContext)
+            );
+        }
+    }
+
     public void testSyntaxErrorsHandling() throws IOException {
 
         KqlParser parser = new KqlParser();
@@ -49,4 +85,32 @@ public void testSyntaxErrorsHandling() throws IOException {
             assertThat(e.getMessage(), equalTo("line 1:15: missing ')' at 'AND'"));
         }
     }
+
+    private static List<String> readQueries(String source) throws Exception {
+        URL url = KqlParserTests.class.getResource(source);
+        Objects.requireNonNull(source, "Cannot find resource " + url);
+
+        List<String> queries = new ArrayList<>();
+
+        try (BufferedReader reader = new BufferedReader(new InputStreamReader(readFromJarUrl(url), StandardCharsets.UTF_8))) {
+            String line;
+
+            while ((line = reader.readLine()) != null) {
+                String query = line.trim();
+                // ignore comments
+                if (query.isEmpty() == false && query.startsWith("//") == false) {
+                    queries.add(line.trim());
+                }
+            }
+        }
+        return queries;
+    }
+
+    @SuppressForbidden(reason = "test reads from jar")
+    private static InputStream readFromJarUrl(URL source) throws IOException {
+        URLConnection con = source.openConnection();
+        // do not to cache files (to avoid keeping file handles around)
+        con.setUseCaches(false);
+        return con.getInputStream();
+    }
 }
diff --git a/x-pack/plugin/kql/src/test/resources/supported-queries b/x-pack/plugin/kql/src/test/resources/supported-queries
new file mode 100644
index 0000000000000..d750f16149112
--- /dev/null
+++ b/x-pack/plugin/kql/src/test/resources/supported-queries
@@ -0,0 +1,111 @@
+// Match all queries
+*
+*:*
+(*:*)
+
+// Queries with no field
+200
+foo
+foo bar
+(foo bar)
+foo*
+*foo
+f*oo
+"foo bar"
+
+// Queries with all fields
+ *:200
+ *:foo
+ *:foo bar
+ *:foo*
+ *:f*oo
+ *: *foo
+ *:"foo bar"
+
+// Querying a field
+foo_field:200
+foo_field:foo
+foo_field:foo bar
+foo_field:(foo bar)
+foo_field:foo*
+foo_field: f*oo
+foo_field: *foo
+foo_field:"foo bar"
+foo_field.subfield:foo
+foo_*_field:foo
+foo_field:*
+foo_*:*
+
+// Range queries
+foo_field<200
+foo_field<foo
+foo_field<"foo bar"
+foo_field>=200
+foo_field>=foo
+foo_field>"foo bar"
+foo_field<=foo
+foo_field>=foo
+
+// Boolean queries
+NOT foo
+NOT foo bar
+NOT foo_field:foo
+NOT foo_field<foo
+foo_field:foo AND foo_field:foo bar
+foo_field<foo AND foo_field>bar
+(foo_field:foo) AND (foo_field:foo bar)
+foo_field:foo OR foo_field:foo bar
+NOT(foo_field:foo OR foo_field:foo bar)
+NOT(foo_field:foo AND foo_field:foo bar)
+NOT foo_field:foo AND NOT foo_field:foo bar
+(NOT foo_field:foo) AND (NOT foo_field:foo bar)
+NOT(foo_field:foo) AND NOT(foo_field:foo bar)
+foo_field:foo AND foo_field:foo bar AND foo bar
+foo_field:foo AND foo_field:foo bar OR foo bar
+foo_field:foo OR foo_field:foo bar OR foo bar
+foo_field:foo OR foo_field:foo bar AND foo bar
+foo_field:foo AND (foo_field:foo bar OR foo bar)
+foo_field:foo AND (foo_field:foo bar OR foo bar)
+foo_field:foo OR (foo_field:foo bar OR foo bar)
+
+// Nested queries
+nested_field: { NOT foo }
+nested_field: { NOT foo bar }
+nested_field: { NOT foo_field:foo }
+nested_field: { foo_field:foo AND foo_field:foo bar }
+nested_field: { foo_field<foo AND foo_field>bar }
+nested_field: { (foo_field:foo) AND (foo_field:foo bar) }
+nested_field: { foo_field:foo OR foo_field:foo bar }
+nested_field: { NOT(foo_field:foo OR foo_field:foo bar) }
+nested_field: { NOT(foo_field:foo AND foo_field:foo bar) }
+nested_field: { NOT foo_field:foo AND NOT foo_field:foo bar }
+nested_field: { (NOT foo_field:foo) AND (NOT foo_field:foo bar) }
+nested_field: { NOT(foo_field:foo) AND NOT(foo_field:foo bar) }
+nested_field: { foo_field:foo AND foo_field:foo bar AND foo bar }
+nested_field: { foo_field:foo AND foo_field:foo bar OR foo bar }
+nested_field: { foo_field:foo OR foo_field:foo bar OR foo bar }
+nested_field: { foo_field:foo OR foo_field:foo bar AND foo bar }
+nested_field: { foo_field:foo AND (foo_field:foo bar OR foo bar) }
+nested_field: { foo_field:foo AND (foo_field:foo bar OR foo bar) }
+nested_field: { foo_field:foo OR (foo_field:foo bar OR foo bar) }
+nested_field: { sub_nested_field : { foo_field:foo } AND foo_field:foo bar }
+
+// Queries with escape sequences
+foo_field : (foo\(bar\))
+foo_field : foo\:bar
+foo_field : (foo \and bar)
+foo_field : (foo \or bar)
+foo_field : foo \not bar
+foo_field : foo \{bar\}
+foo_field : foo \(bar\)
+foo_field : foo \\ bar
+foo_field : foo \"bar\"
+
+foo_field : "foo and bar"
+foo_field : "foo not bar"
+foo_field : "foo or bar"
+foo_field : "foo : bar"
+foo_field : "foo { bar }"
+foo_field : "foo (bar)"
+foo_field : "foo \\ bar"
+foo_field : "foo \"bar\""
diff --git a/x-pack/plugin/kql/src/test/resources/unsupported-queries b/x-pack/plugin/kql/src/test/resources/unsupported-queries
new file mode 100644
index 0000000000000..31e1544863bfb
--- /dev/null
+++ b/x-pack/plugin/kql/src/test/resources/unsupported-queries
@@ -0,0 +1,42 @@
+
+// Incomplete expressions
+foo_field :
+foo_field <
+foo_field >
+foo_field >=
+foo_field <=
+
+// Parentheses mismatch
+foo_field: (foo bar
+foo_field: foo bar)
+NOT foo_field:foo OR foo_field:foo bar)
+NOT (foo_field:foo AND) foo_field:foo bar
+
+// Quotes mismatch
+foo_field: "foo bar
+foo_field: foo bar"
+
+
+// Invalid boolean queries
+foo AND
+AND foo
+foo OR
+OR foo
+NOT foo:
+
+// Can't nest grouping terms parentheses
+foo_field:(foo (bar))
+
+// Bad syntax for nested fields:
+nested_field { foo: bar }
+
+// Missing escape sequences:
+foo_field: foo:bar
+foo_field: (foo and bar)
+foo_field: (foo or bar)
+foo_field: foo not bar
+foo_field: foo { bar }
+foo_field: foo (bar)
+foo_field: foo "bar"
+foo_field: "foo\ bar"
+foo_field: "foo "bar""