diff --git a/docs/reference/modules/scripting/painless.asciidoc b/docs/reference/modules/scripting/painless.asciidoc
index cb28e735e5c..20b301bda31 100644
--- a/docs/reference/modules/scripting/painless.asciidoc
+++ b/docs/reference/modules/scripting/painless.asciidoc
@@ -202,12 +202,15 @@ POST hockey/player/1/_update
 // CONSOLE
 
 [float]
+[[modules-scripting-painless-regex]]
 === Regular expressions
 
 Painless's native support for regular expressions has syntax constructs:
 
 * `/pattern/`: Pattern literals create patterns. This is the only way to create
-a pattern in painless.
+a pattern in painless. The pattern inside the `/`s are just
+http://docs.oracle.com/javase/8/docs/api/java/util/regex/Pattern.html[Java regular expressions].
+See <<modules-scripting-painless-regex-flags>> for more.
 * `=~`: The find operator return a `boolean`, `true` if a subsequence of the
 text matches, `false` otherwise.
 * `==~`: The match operator returns a `boolean`, `true` if the text matches,
@@ -265,14 +268,35 @@ Note: all of the `_update_by_query` examples above could really do with a
 because script queries aren't able to use the inverted index to limit the
 documents that they have to check.
 
-The pattern syntax is just
-http://docs.oracle.com/javase/8/docs/api/java/util/regex/Pattern.html[Java regular expressions].
 We intentionally don't allow scripts to call `Pattern.compile` to get a new
 pattern on the fly because building a `Pattern` is (comparatively) slow.
 Pattern literals (`/apattern/`) have fancy constant extraction so no matter
 where they show up in the painless script they are built only when the script
 is first used. It is fairly similar to how `String` literals work in Java.
 
+[float]
+[[modules-scripting-painless-regex-flags]]
+==== Regular expression flags
+
+You can define flags on patterns in Painless by adding characters after the
+trailing `/` like `/foo/i` or `/foo \w #comment/iUx`. Painless exposes all the
+flags from
+https://docs.oracle.com/javase/7/docs/api/java/util/regex/Pattern.html[Java's Pattern class]
+using these characters:
+
+[cols="<,<,<",options="header",]
+|=======================================================================
+| Character | Java Constant | Example
+|`c` | CANON_EQ                  | `'å' ==~ /å/c` (open in hex editor to see)
+|`i` | CASE_INSENSITIVE          | `'A' ==~ /a/i`
+|`l` | LITERAL                   | `'[a]' ==~ /[a]/l`
+|`m` | MULTILINE                 | `'a\nb\nc' =~ /^b$/m`
+|`s` | DOTALL (aka single line)  | `'a\nb\nc' =~ /.b./s`
+|`U` | UNICODE_CHARACTER_CLASS   | `'Ɛ' ==~ /\\w/U`
+|`u` | UNICODE_CASE              | `'Ɛ' ==~ /ɛ/iu`
+|`x` | COMMENTS (aka extended)   | `'a' ==~ /a #comment/x`
+|=======================================================================
+
 
 [[painless-api]]
 [float]
diff --git a/modules/lang-painless/src/main/antlr/PainlessLexer.g4 b/modules/lang-painless/src/main/antlr/PainlessLexer.g4
index a31c50ee198..62a154db40c 100644
--- a/modules/lang-painless/src/main/antlr/PainlessLexer.g4
+++ b/modules/lang-painless/src/main/antlr/PainlessLexer.g4
@@ -104,7 +104,7 @@ INTEGER: ( '0' | [1-9] [0-9]* ) [lLfFdD]?;
 DECIMAL: ( '0' | [1-9] [0-9]* ) (DOT [0-9]+)? ( [eE] [+\-]? [0-9]+ )? [fF]?;
 
 STRING: ( '"' ( '\\"' | '\\\\' | ~[\\"] )*? '"' ) | ( '\'' ( '\\\'' | '\\\\' | ~[\\"] )*? '\'' );
-REGEX: '/' ( ~('/' | '\n') | '\\' ~'\n' )+ '/' { SlashStrategy.slashIsRegex(_factory) }?;
+REGEX: '/' ( ~('/' | '\n') | '\\' ~'\n' )+ '/' [cilmsUux]* { SlashStrategy.slashIsRegex(_factory) }?;
 
 TRUE:  'true';
 FALSE: 'false';
diff --git a/modules/lang-painless/src/main/java/org/elasticsearch/painless/WriterConstants.java b/modules/lang-painless/src/main/java/org/elasticsearch/painless/WriterConstants.java
index d798bb5ca68..6960e906339 100644
--- a/modules/lang-painless/src/main/java/org/elasticsearch/painless/WriterConstants.java
+++ b/modules/lang-painless/src/main/java/org/elasticsearch/painless/WriterConstants.java
@@ -79,7 +79,7 @@ public final class WriterConstants {
      * because it can do it statically. This is both faster and prevents the script from doing something super slow like building a regex
      * per time it is run.
      */
-    public final static Method PATTERN_COMPILE = getAsmMethod(Pattern.class, "compile", String.class);
+    public final static Method PATTERN_COMPILE = getAsmMethod(Pattern.class, "compile", String.class, int.class);
     public final static Method PATTERN_MATCHER = getAsmMethod(Matcher.class, "matcher", CharSequence.class);
     public final static Method MATCHER_MATCHES = getAsmMethod(boolean.class, "matches");
     public final static Method MATCHER_FIND = getAsmMethod(boolean.class, "find");
diff --git a/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/PainlessLexer.java b/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/PainlessLexer.java
index 040d17c521b..cf0ac8605f0 100644
--- a/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/PainlessLexer.java
+++ b/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/PainlessLexer.java
@@ -160,7 +160,7 @@ class PainlessLexer extends Lexer {
   }
 
   public static final String _serializedATN =
-    "\3\u0430\ud6d1\u8206\uad2d\u4417\uaef1\u8d80\uaadd\2R\u0233\b\1\b\1\4"+
+    "\3\u0430\ud6d1\u8206\uad2d\u4417\uaef1\u8d80\uaadd\2R\u0239\b\1\b\1\4"+
     "\2\t\2\4\3\t\3\4\4\t\4\4\5\t\5\4\6\t\6\4\7\t\7\4\b\t\b\4\t\t\t\4\n\t\n"+
     "\4\13\t\13\4\f\t\f\4\r\t\r\4\16\t\16\4\17\t\17\4\20\t\20\4\21\t\21\4\22"+
     "\t\22\4\23\t\23\4\24\t\24\4\25\t\25\4\26\t\26\4\27\t\27\4\30\t\30\4\31"+
@@ -191,171 +191,174 @@ class PainlessLexer extends Lexer {
     "\5H\u01c8\nH\3H\3H\5H\u01cc\nH\3H\6H\u01cf\nH\rH\16H\u01d0\5H\u01d3\n"+
     "H\3H\5H\u01d6\nH\3I\3I\3I\3I\3I\3I\7I\u01de\nI\fI\16I\u01e1\13I\3I\3I"+
     "\3I\3I\3I\3I\3I\7I\u01ea\nI\fI\16I\u01ed\13I\3I\5I\u01f0\nI\3J\3J\3J\3"+
-    "J\6J\u01f6\nJ\rJ\16J\u01f7\3J\3J\3J\3K\3K\3K\3K\3K\3L\3L\3L\3L\3L\3L\3"+
-    "M\3M\3M\3M\3M\3N\3N\3N\3N\7N\u0211\nN\fN\16N\u0214\13N\3N\3N\3O\3O\7O"+
-    "\u021a\nO\fO\16O\u021d\13O\3P\3P\3P\7P\u0222\nP\fP\16P\u0225\13P\5P\u0227"+
-    "\nP\3P\3P\3Q\3Q\7Q\u022d\nQ\fQ\16Q\u0230\13Q\3Q\3Q\6\u00b1\u00bb\u01df"+
-    "\u01eb\2R\4\3\6\4\b\5\n\6\f\7\16\b\20\t\22\n\24\13\26\f\30\r\32\16\34"+
-    "\17\36\20 \21\"\22$\23&\24(\25*\26,\27.\30\60\31\62\32\64\33\66\348\35"+
-    ":\36<\37> @!B\"D#F$H%J&L\'N(P)R*T+V,X-Z.\\/^\60`\61b\62d\63f\64h\65j\66"+
-    "l\67n8p9r:t;v<x=z>|?~@\u0080A\u0082B\u0084C\u0086D\u0088E\u008aF\u008c"+
-    "G\u008eH\u0090I\u0092J\u0094K\u0096L\u0098M\u009aN\u009cO\u009eP\u00a0"+
-    "Q\u00a2R\4\2\3\23\5\2\13\f\17\17\"\"\4\2\f\f\17\17\3\2\629\4\2NNnn\4\2"+
-    "ZZzz\5\2\62;CHch\3\2\63;\3\2\62;\b\2FFHHNNffhhnn\4\2GGgg\4\2--//\4\2H"+
-    "Hhh\4\2$$^^\4\2\f\f\61\61\3\2\f\f\5\2C\\aac|\6\2\62;C\\aac|\u0252\2\4"+
-    "\3\2\2\2\2\6\3\2\2\2\2\b\3\2\2\2\2\n\3\2\2\2\2\f\3\2\2\2\2\16\3\2\2\2"+
-    "\2\20\3\2\2\2\2\22\3\2\2\2\2\24\3\2\2\2\2\26\3\2\2\2\2\30\3\2\2\2\2\32"+
-    "\3\2\2\2\2\34\3\2\2\2\2\36\3\2\2\2\2 \3\2\2\2\2\"\3\2\2\2\2$\3\2\2\2\2"+
-    "&\3\2\2\2\2(\3\2\2\2\2*\3\2\2\2\2,\3\2\2\2\2.\3\2\2\2\2\60\3\2\2\2\2\62"+
-    "\3\2\2\2\2\64\3\2\2\2\2\66\3\2\2\2\28\3\2\2\2\2:\3\2\2\2\2<\3\2\2\2\2"+
-    ">\3\2\2\2\2@\3\2\2\2\2B\3\2\2\2\2D\3\2\2\2\2F\3\2\2\2\2H\3\2\2\2\2J\3"+
-    "\2\2\2\2L\3\2\2\2\2N\3\2\2\2\2P\3\2\2\2\2R\3\2\2\2\2T\3\2\2\2\2V\3\2\2"+
-    "\2\2X\3\2\2\2\2Z\3\2\2\2\2\\\3\2\2\2\2^\3\2\2\2\2`\3\2\2\2\2b\3\2\2\2"+
-    "\2d\3\2\2\2\2f\3\2\2\2\2h\3\2\2\2\2j\3\2\2\2\2l\3\2\2\2\2n\3\2\2\2\2p"+
-    "\3\2\2\2\2r\3\2\2\2\2t\3\2\2\2\2v\3\2\2\2\2x\3\2\2\2\2z\3\2\2\2\2|\3\2"+
-    "\2\2\2~\3\2\2\2\2\u0080\3\2\2\2\2\u0082\3\2\2\2\2\u0084\3\2\2\2\2\u0086"+
-    "\3\2\2\2\2\u0088\3\2\2\2\2\u008a\3\2\2\2\2\u008c\3\2\2\2\2\u008e\3\2\2"+
-    "\2\2\u0090\3\2\2\2\2\u0092\3\2\2\2\2\u0094\3\2\2\2\2\u0096\3\2\2\2\2\u0098"+
-    "\3\2\2\2\2\u009a\3\2\2\2\2\u009c\3\2\2\2\2\u009e\3\2\2\2\3\u00a0\3\2\2"+
-    "\2\3\u00a2\3\2\2\2\4\u00a5\3\2\2\2\6\u00c0\3\2\2\2\b\u00c4\3\2\2\2\n\u00c6"+
-    "\3\2\2\2\f\u00c8\3\2\2\2\16\u00ca\3\2\2\2\20\u00cc\3\2\2\2\22\u00ce\3"+
-    "\2\2\2\24\u00d0\3\2\2\2\26\u00d4\3\2\2\2\30\u00d6\3\2\2\2\32\u00d8\3\2"+
-    "\2\2\34\u00db\3\2\2\2\36\u00e0\3\2\2\2 \u00e6\3\2\2\2\"\u00e9\3\2\2\2"+
-    "$\u00ed\3\2\2\2&\u00f6\3\2\2\2(\u00fc\3\2\2\2*\u0103\3\2\2\2,\u0107\3"+
-    "\2\2\2.\u010b\3\2\2\2\60\u0111\3\2\2\2\62\u0117\3\2\2\2\64\u011c\3\2\2"+
-    "\2\66\u011e\3\2\2\28\u0120\3\2\2\2:\u0122\3\2\2\2<\u0125\3\2\2\2>\u0127"+
-    "\3\2\2\2@\u0129\3\2\2\2B\u012b\3\2\2\2D\u012e\3\2\2\2F\u0131\3\2\2\2H"+
-    "\u0135\3\2\2\2J\u0137\3\2\2\2L\u013a\3\2\2\2N\u013c\3\2\2\2P\u013f\3\2"+
-    "\2\2R\u0142\3\2\2\2T\u0146\3\2\2\2V\u0149\3\2\2\2X\u014d\3\2\2\2Z\u014f"+
-    "\3\2\2\2\\\u0151\3\2\2\2^\u0153\3\2\2\2`\u0156\3\2\2\2b\u0159\3\2\2\2"+
-    "d\u015b\3\2\2\2f\u015d\3\2\2\2h\u0160\3\2\2\2j\u0163\3\2\2\2l\u0166\3"+
-    "\2\2\2n\u016a\3\2\2\2p\u016d\3\2\2\2r\u0170\3\2\2\2t\u0172\3\2\2\2v\u0175"+
-    "\3\2\2\2x\u0178\3\2\2\2z\u017b\3\2\2\2|\u017e\3\2\2\2~\u0181\3\2\2\2\u0080"+
-    "\u0184\3\2\2\2\u0082\u0187\3\2\2\2\u0084\u018a\3\2\2\2\u0086\u018e\3\2"+
-    "\2\2\u0088\u0192\3\2\2\2\u008a\u0197\3\2\2\2\u008c\u01a0\3\2\2\2\u008e"+
-    "\u01b2\3\2\2\2\u0090\u01bf\3\2\2\2\u0092\u01ef\3\2\2\2\u0094\u01f1\3\2"+
-    "\2\2\u0096\u01fc\3\2\2\2\u0098\u0201\3\2\2\2\u009a\u0207\3\2\2\2\u009c"+
-    "\u020c\3\2\2\2\u009e\u0217\3\2\2\2\u00a0\u0226\3\2\2\2\u00a2\u022a\3\2"+
-    "\2\2\u00a4\u00a6\t\2\2\2\u00a5\u00a4\3\2\2\2\u00a6\u00a7\3\2\2\2\u00a7"+
-    "\u00a5\3\2\2\2\u00a7\u00a8\3\2\2\2\u00a8\u00a9\3\2\2\2\u00a9\u00aa\b\2"+
-    "\2\2\u00aa\5\3\2\2\2\u00ab\u00ac\7\61\2\2\u00ac\u00ad\7\61\2\2\u00ad\u00b1"+
-    "\3\2\2\2\u00ae\u00b0\13\2\2\2\u00af\u00ae\3\2\2\2\u00b0\u00b3\3\2\2\2"+
-    "\u00b1\u00b2\3\2\2\2\u00b1\u00af\3\2\2\2\u00b2\u00b4\3\2\2\2\u00b3\u00b1"+
-    "\3\2\2\2\u00b4\u00c1\t\3\2\2\u00b5\u00b6\7\61\2\2\u00b6\u00b7\7,\2\2\u00b7"+
-    "\u00bb\3\2\2\2\u00b8\u00ba\13\2\2\2\u00b9\u00b8\3\2\2\2\u00ba\u00bd\3"+
-    "\2\2\2\u00bb\u00bc\3\2\2\2\u00bb\u00b9\3\2\2\2\u00bc\u00be\3\2\2\2\u00bd"+
-    "\u00bb\3\2\2\2\u00be\u00bf\7,\2\2\u00bf\u00c1\7\61\2\2\u00c0\u00ab\3\2"+
-    "\2\2\u00c0\u00b5\3\2\2\2\u00c1\u00c2\3\2\2\2\u00c2\u00c3\b\3\2\2\u00c3"+
-    "\7\3\2\2\2\u00c4\u00c5\7}\2\2\u00c5\t\3\2\2\2\u00c6\u00c7\7\177\2\2\u00c7"+
-    "\13\3\2\2\2\u00c8\u00c9\7]\2\2\u00c9\r\3\2\2\2\u00ca\u00cb\7_\2\2\u00cb"+
-    "\17\3\2\2\2\u00cc\u00cd\7*\2\2\u00cd\21\3\2\2\2\u00ce\u00cf\7+\2\2\u00cf"+
-    "\23\3\2\2\2\u00d0\u00d1\7\60\2\2\u00d1\u00d2\3\2\2\2\u00d2\u00d3\b\n\3"+
-    "\2\u00d3\25\3\2\2\2\u00d4\u00d5\7.\2\2\u00d5\27\3\2\2\2\u00d6\u00d7\7"+
-    "=\2\2\u00d7\31\3\2\2\2\u00d8\u00d9\7k\2\2\u00d9\u00da\7h\2\2\u00da\33"+
-    "\3\2\2\2\u00db\u00dc\7g\2\2\u00dc\u00dd\7n\2\2\u00dd\u00de\7u\2\2\u00de"+
-    "\u00df\7g\2\2\u00df\35\3\2\2\2\u00e0\u00e1\7y\2\2\u00e1\u00e2\7j\2\2\u00e2"+
-    "\u00e3\7k\2\2\u00e3\u00e4\7n\2\2\u00e4\u00e5\7g\2\2\u00e5\37\3\2\2\2\u00e6"+
-    "\u00e7\7f\2\2\u00e7\u00e8\7q\2\2\u00e8!\3\2\2\2\u00e9\u00ea\7h\2\2\u00ea"+
-    "\u00eb\7q\2\2\u00eb\u00ec\7t\2\2\u00ec#\3\2\2\2\u00ed\u00ee\7e\2\2\u00ee"+
-    "\u00ef\7q\2\2\u00ef\u00f0\7p\2\2\u00f0\u00f1\7v\2\2\u00f1\u00f2\7k\2\2"+
-    "\u00f2\u00f3\7p\2\2\u00f3\u00f4\7w\2\2\u00f4\u00f5\7g\2\2\u00f5%\3\2\2"+
-    "\2\u00f6\u00f7\7d\2\2\u00f7\u00f8\7t\2\2\u00f8\u00f9\7g\2\2\u00f9\u00fa"+
-    "\7c\2\2\u00fa\u00fb\7m\2\2\u00fb\'\3\2\2\2\u00fc\u00fd\7t\2\2\u00fd\u00fe"+
-    "\7g\2\2\u00fe\u00ff\7v\2\2\u00ff\u0100\7w\2\2\u0100\u0101\7t\2\2\u0101"+
-    "\u0102\7p\2\2\u0102)\3\2\2\2\u0103\u0104\7p\2\2\u0104\u0105\7g\2\2\u0105"+
-    "\u0106\7y\2\2\u0106+\3\2\2\2\u0107\u0108\7v\2\2\u0108\u0109\7t\2\2\u0109"+
-    "\u010a\7{\2\2\u010a-\3\2\2\2\u010b\u010c\7e\2\2\u010c\u010d\7c\2\2\u010d"+
-    "\u010e\7v\2\2\u010e\u010f\7e\2\2\u010f\u0110\7j\2\2\u0110/\3\2\2\2\u0111"+
-    "\u0112\7v\2\2\u0112\u0113\7j\2\2\u0113\u0114\7t\2\2\u0114\u0115\7q\2\2"+
-    "\u0115\u0116\7y\2\2\u0116\61\3\2\2\2\u0117\u0118\7v\2\2\u0118\u0119\7"+
-    "j\2\2\u0119\u011a\7k\2\2\u011a\u011b\7u\2\2\u011b\63\3\2\2\2\u011c\u011d"+
-    "\7#\2\2\u011d\65\3\2\2\2\u011e\u011f\7\u0080\2\2\u011f\67\3\2\2\2\u0120"+
-    "\u0121\7,\2\2\u01219\3\2\2\2\u0122\u0123\7\61\2\2\u0123\u0124\6\35\2\2"+
-    "\u0124;\3\2\2\2\u0125\u0126\7\'\2\2\u0126=\3\2\2\2\u0127\u0128\7-\2\2"+
-    "\u0128?\3\2\2\2\u0129\u012a\7/\2\2\u012aA\3\2\2\2\u012b\u012c\7>\2\2\u012c"+
-    "\u012d\7>\2\2\u012dC\3\2\2\2\u012e\u012f\7@\2\2\u012f\u0130\7@\2\2\u0130"+
-    "E\3\2\2\2\u0131\u0132\7@\2\2\u0132\u0133\7@\2\2\u0133\u0134\7@\2\2\u0134"+
-    "G\3\2\2\2\u0135\u0136\7>\2\2\u0136I\3\2\2\2\u0137\u0138\7>\2\2\u0138\u0139"+
-    "\7?\2\2\u0139K\3\2\2\2\u013a\u013b\7@\2\2\u013bM\3\2\2\2\u013c\u013d\7"+
-    "@\2\2\u013d\u013e\7?\2\2\u013eO\3\2\2\2\u013f\u0140\7?\2\2\u0140\u0141"+
-    "\7?\2\2\u0141Q\3\2\2\2\u0142\u0143\7?\2\2\u0143\u0144\7?\2\2\u0144\u0145"+
-    "\7?\2\2\u0145S\3\2\2\2\u0146\u0147\7#\2\2\u0147\u0148\7?\2\2\u0148U\3"+
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+    "\2\2\2\u00bb\u00b9\3\2\2\2\u00bc\u00be\3\2\2\2\u00bd\u00bb\3\2\2\2\u00be"+
+    "\u00bf\7,\2\2\u00bf\u00c1\7\61\2\2\u00c0\u00ab\3\2\2\2\u00c0\u00b5\3\2"+
+    "\2\2\u00c1\u00c2\3\2\2\2\u00c2\u00c3\b\3\2\2\u00c3\7\3\2\2\2\u00c4\u00c5"+
+    "\7}\2\2\u00c5\t\3\2\2\2\u00c6\u00c7\7\177\2\2\u00c7\13\3\2\2\2\u00c8\u00c9"+
+    "\7]\2\2\u00c9\r\3\2\2\2\u00ca\u00cb\7_\2\2\u00cb\17\3\2\2\2\u00cc\u00cd"+
+    "\7*\2\2\u00cd\21\3\2\2\2\u00ce\u00cf\7+\2\2\u00cf\23\3\2\2\2\u00d0\u00d1"+
+    "\7\60\2\2\u00d1\u00d2\3\2\2\2\u00d2\u00d3\b\n\3\2\u00d3\25\3\2\2\2\u00d4"+
+    "\u00d5\7.\2\2\u00d5\27\3\2\2\2\u00d6\u00d7\7=\2\2\u00d7\31\3\2\2\2\u00d8"+
+    "\u00d9\7k\2\2\u00d9\u00da\7h\2\2\u00da\33\3\2\2\2\u00db\u00dc\7g\2\2\u00dc"+
+    "\u00dd\7n\2\2\u00dd\u00de\7u\2\2\u00de\u00df\7g\2\2\u00df\35\3\2\2\2\u00e0"+
+    "\u00e1\7y\2\2\u00e1\u00e2\7j\2\2\u00e2\u00e3\7k\2\2\u00e3\u00e4\7n\2\2"+
+    "\u00e4\u00e5\7g\2\2\u00e5\37\3\2\2\2\u00e6\u00e7\7f\2\2\u00e7\u00e8\7"+
+    "q\2\2\u00e8!\3\2\2\2\u00e9\u00ea\7h\2\2\u00ea\u00eb\7q\2\2\u00eb\u00ec"+
+    "\7t\2\2\u00ec#\3\2\2\2\u00ed\u00ee\7e\2\2\u00ee\u00ef\7q\2\2\u00ef\u00f0"+
+    "\7p\2\2\u00f0\u00f1\7v\2\2\u00f1\u00f2\7k\2\2\u00f2\u00f3\7p\2\2\u00f3"+
+    "\u00f4\7w\2\2\u00f4\u00f5\7g\2\2\u00f5%\3\2\2\2\u00f6\u00f7\7d\2\2\u00f7"+
+    "\u00f8\7t\2\2\u00f8\u00f9\7g\2\2\u00f9\u00fa\7c\2\2\u00fa\u00fb\7m\2\2"+
+    "\u00fb\'\3\2\2\2\u00fc\u00fd\7t\2\2\u00fd\u00fe\7g\2\2\u00fe\u00ff\7v"+
+    "\2\2\u00ff\u0100\7w\2\2\u0100\u0101\7t\2\2\u0101\u0102\7p\2\2\u0102)\3"+
+    "\2\2\2\u0103\u0104\7p\2\2\u0104\u0105\7g\2\2\u0105\u0106\7y\2\2\u0106"+
+    "+\3\2\2\2\u0107\u0108\7v\2\2\u0108\u0109\7t\2\2\u0109\u010a\7{\2\2\u010a"+
+    "-\3\2\2\2\u010b\u010c\7e\2\2\u010c\u010d\7c\2\2\u010d\u010e\7v\2\2\u010e"+
+    "\u010f\7e\2\2\u010f\u0110\7j\2\2\u0110/\3\2\2\2\u0111\u0112\7v\2\2\u0112"+
+    "\u0113\7j\2\2\u0113\u0114\7t\2\2\u0114\u0115\7q\2\2\u0115\u0116\7y\2\2"+
+    "\u0116\61\3\2\2\2\u0117\u0118\7v\2\2\u0118\u0119\7j\2\2\u0119\u011a\7"+
+    "k\2\2\u011a\u011b\7u\2\2\u011b\63\3\2\2\2\u011c\u011d\7#\2\2\u011d\65"+
+    "\3\2\2\2\u011e\u011f\7\u0080\2\2\u011f\67\3\2\2\2\u0120\u0121\7,\2\2\u0121"+
+    "9\3\2\2\2\u0122\u0123\7\61\2\2\u0123\u0124\6\35\2\2\u0124;\3\2\2\2\u0125"+
+    "\u0126\7\'\2\2\u0126=\3\2\2\2\u0127\u0128\7-\2\2\u0128?\3\2\2\2\u0129"+
+    "\u012a\7/\2\2\u012aA\3\2\2\2\u012b\u012c\7>\2\2\u012c\u012d\7>\2\2\u012d"+
+    "C\3\2\2\2\u012e\u012f\7@\2\2\u012f\u0130\7@\2\2\u0130E\3\2\2\2\u0131\u0132"+
+    "\7@\2\2\u0132\u0133\7@\2\2\u0133\u0134\7@\2\2\u0134G\3\2\2\2\u0135\u0136"+
+    "\7>\2\2\u0136I\3\2\2\2\u0137\u0138\7>\2\2\u0138\u0139\7?\2\2\u0139K\3"+
+    "\2\2\2\u013a\u013b\7@\2\2\u013bM\3\2\2\2\u013c\u013d\7@\2\2\u013d\u013e"+
+    "\7?\2\2\u013eO\3\2\2\2\u013f\u0140\7?\2\2\u0140\u0141\7?\2\2\u0141Q\3"+
+    "\2\2\2\u0142\u0143\7?\2\2\u0143\u0144\7?\2\2\u0144\u0145\7?\2\2\u0145"+
+    "S\3\2\2\2\u0146\u0147\7#\2\2\u0147\u0148\7?\2\2\u0148U\3\2\2\2\u0149\u014a"+
+    "\7#\2\2\u014a\u014b\7?\2\2\u014b\u014c\7?\2\2\u014cW\3\2\2\2\u014d\u014e"+
+    "\7(\2\2\u014eY\3\2\2\2\u014f\u0150\7`\2\2\u0150[\3\2\2\2\u0151\u0152\7"+
+    "~\2\2\u0152]\3\2\2\2\u0153\u0154\7(\2\2\u0154\u0155\7(\2\2\u0155_\3\2"+
+    "\2\2\u0156\u0157\7~\2\2\u0157\u0158\7~\2\2\u0158a\3\2\2\2\u0159\u015a"+
+    "\7A\2\2\u015ac\3\2\2\2\u015b\u015c\7<\2\2\u015ce\3\2\2\2\u015d\u015e\7"+
+    "<\2\2\u015e\u015f\7<\2\2\u015fg\3\2\2\2\u0160\u0161\7/\2\2\u0161\u0162"+
+    "\7@\2\2\u0162i\3\2\2\2\u0163\u0164\7?\2\2\u0164\u0165\7\u0080\2\2\u0165"+
+    "k\3\2\2\2\u0166\u0167\7?\2\2\u0167\u0168\7?\2\2\u0168\u0169\7\u0080\2"+
+    "\2\u0169m\3\2\2\2\u016a\u016b\7-\2\2\u016b\u016c\7-\2\2\u016co\3\2\2\2"+
+    "\u016d\u016e\7/\2\2\u016e\u016f\7/\2\2\u016fq\3\2\2\2\u0170\u0171\7?\2"+
+    "\2\u0171s\3\2\2\2\u0172\u0173\7-\2\2\u0173\u0174\7?\2\2\u0174u\3\2\2\2"+
+    "\u0175\u0176\7/\2\2\u0176\u0177\7?\2\2\u0177w\3\2\2\2\u0178\u0179\7,\2"+
+    "\2\u0179\u017a\7?\2\2\u017ay\3\2\2\2\u017b\u017c\7\61\2\2\u017c\u017d"+
+    "\7?\2\2\u017d{\3\2\2\2\u017e\u017f\7\'\2\2\u017f\u0180\7?\2\2\u0180}\3"+
+    "\2\2\2\u0181\u0182\7(\2\2\u0182\u0183\7?\2\2\u0183\177\3\2\2\2\u0184\u0185"+
+    "\7`\2\2\u0185\u0186\7?\2\2\u0186\u0081\3\2\2\2\u0187\u0188\7~\2\2\u0188"+
+    "\u0189\7?\2\2\u0189\u0083\3\2\2\2\u018a\u018b\7>\2\2\u018b\u018c\7>\2"+
+    "\2\u018c\u018d\7?\2\2\u018d\u0085\3\2\2\2\u018e\u018f\7@\2\2\u018f\u0190"+
+    "\7@\2\2\u0190\u0191\7?\2\2\u0191\u0087\3\2\2\2\u0192\u0193\7@\2\2\u0193"+
+    "\u0194\7@\2\2\u0194\u0195\7@\2\2\u0195\u0196\7?\2\2\u0196\u0089\3\2\2"+
+    "\2\u0197\u0199\7\62\2\2\u0198\u019a\t\4\2\2\u0199\u0198\3\2\2\2\u019a"+
+    "\u019b\3\2\2\2\u019b\u0199\3\2\2\2\u019b\u019c\3\2\2\2\u019c\u019e\3\2"+
+    "\2\2\u019d\u019f\t\5\2\2\u019e\u019d\3\2\2\2\u019e\u019f\3\2\2\2\u019f"+
+    "\u008b\3\2\2\2\u01a0\u01a1\7\62\2\2\u01a1\u01a3\t\6\2\2\u01a2\u01a4\t"+
+    "\7\2\2\u01a3\u01a2\3\2\2\2\u01a4\u01a5\3\2\2\2\u01a5\u01a3\3\2\2\2\u01a5"+
+    "\u01a6\3\2\2\2\u01a6\u01a8\3\2\2\2\u01a7\u01a9\t\5\2\2\u01a8\u01a7\3\2"+
+    "\2\2\u01a8\u01a9\3\2\2\2\u01a9\u008d\3\2\2\2\u01aa\u01b3\7\62\2\2\u01ab"+
+    "\u01af\t\b\2\2\u01ac\u01ae\t\t\2\2\u01ad\u01ac\3\2\2\2\u01ae\u01b1\3\2"+
+    "\2\2\u01af\u01ad\3\2\2\2\u01af\u01b0\3\2\2\2\u01b0\u01b3\3\2\2\2\u01b1"+
+    "\u01af\3\2\2\2\u01b2\u01aa\3\2\2\2\u01b2\u01ab\3\2\2\2\u01b3\u01b5\3\2"+
+    "\2\2\u01b4\u01b6\t\n\2\2\u01b5\u01b4\3\2\2\2\u01b5\u01b6\3\2\2\2\u01b6"+
+    "\u008f\3\2\2\2\u01b7\u01c0\7\62\2\2\u01b8\u01bc\t\b\2\2\u01b9\u01bb\t"+
+    "\t\2\2\u01ba\u01b9\3\2\2\2\u01bb\u01be\3\2\2\2\u01bc\u01ba\3\2\2\2\u01bc"+
+    "\u01bd\3\2\2\2\u01bd\u01c0\3\2\2\2\u01be\u01bc\3\2\2\2\u01bf\u01b7\3\2"+
+    "\2\2\u01bf\u01b8\3\2\2\2\u01c0\u01c7\3\2\2\2\u01c1\u01c3\5\24\n\2\u01c2"+
+    "\u01c4\t\t\2\2\u01c3\u01c2\3\2\2\2\u01c4\u01c5\3\2\2\2\u01c5\u01c3\3\2"+
+    "\2\2\u01c5\u01c6\3\2\2\2\u01c6\u01c8\3\2\2\2\u01c7\u01c1\3\2\2\2\u01c7"+
+    "\u01c8\3\2\2\2\u01c8\u01d2\3\2\2\2\u01c9\u01cb\t\13\2\2\u01ca\u01cc\t"+
+    "\f\2\2\u01cb\u01ca\3\2\2\2\u01cb\u01cc\3\2\2\2\u01cc\u01ce\3\2\2\2\u01cd"+
+    "\u01cf\t\t\2\2\u01ce\u01cd\3\2\2\2\u01cf\u01d0\3\2\2\2\u01d0\u01ce\3\2"+
+    "\2\2\u01d0\u01d1\3\2\2\2\u01d1\u01d3\3\2\2\2\u01d2\u01c9\3\2\2\2\u01d2"+
+    "\u01d3\3\2\2\2\u01d3\u01d5\3\2\2\2\u01d4\u01d6\t\r\2\2\u01d5\u01d4\3\2"+
+    "\2\2\u01d5\u01d6\3\2\2\2\u01d6\u0091\3\2\2\2\u01d7\u01df\7$\2\2\u01d8"+
+    "\u01d9\7^\2\2\u01d9\u01de\7$\2\2\u01da\u01db\7^\2\2\u01db\u01de\7^\2\2"+
+    "\u01dc\u01de\n\16\2\2\u01dd\u01d8\3\2\2\2\u01dd\u01da\3\2\2\2\u01dd\u01dc"+
+    "\3\2\2\2\u01de\u01e1\3\2\2\2\u01df\u01e0\3\2\2\2\u01df\u01dd\3\2\2\2\u01e0"+
+    "\u01e2\3\2\2\2\u01e1\u01df\3\2\2\2\u01e2\u01f0\7$\2\2\u01e3\u01eb\7)\2"+
+    "\2\u01e4\u01e5\7^\2\2\u01e5\u01ea\7)\2\2\u01e6\u01e7\7^\2\2\u01e7\u01ea"+
+    "\7^\2\2\u01e8\u01ea\n\16\2\2\u01e9\u01e4\3\2\2\2\u01e9\u01e6\3\2\2\2\u01e9"+
+    "\u01e8\3\2\2\2\u01ea\u01ed\3\2\2\2\u01eb\u01ec\3\2\2\2\u01eb\u01e9\3\2"+
+    "\2\2\u01ec\u01ee\3\2\2\2\u01ed\u01eb\3\2\2\2\u01ee\u01f0\7)\2\2\u01ef"+
+    "\u01d7\3\2\2\2\u01ef\u01e3\3\2\2\2\u01f0\u0093\3\2\2\2\u01f1\u01f5\7\61"+
+    "\2\2\u01f2\u01f6\n\17\2\2\u01f3\u01f4\7^\2\2\u01f4\u01f6\n\20\2\2\u01f5"+
+    "\u01f2\3\2\2\2\u01f5\u01f3\3\2\2\2\u01f6\u01f7\3\2\2\2\u01f7\u01f5\3\2"+
+    "\2\2\u01f7\u01f8\3\2\2\2\u01f8\u01f9\3\2\2\2\u01f9\u01fd\7\61\2\2\u01fa"+
+    "\u01fc\t\21\2\2\u01fb\u01fa\3\2\2\2\u01fc\u01ff\3\2\2\2\u01fd\u01fb\3"+
+    "\2\2\2\u01fd\u01fe\3\2\2\2\u01fe\u0200\3\2\2\2\u01ff\u01fd\3\2\2\2\u0200"+
+    "\u0201\6J\3\2\u0201\u0095\3\2\2\2\u0202\u0203\7v\2\2\u0203\u0204\7t\2"+
+    "\2\u0204\u0205\7w\2\2\u0205\u0206\7g\2\2\u0206\u0097\3\2\2\2\u0207\u0208"+
+    "\7h\2\2\u0208\u0209\7c\2\2\u0209\u020a\7n\2\2\u020a\u020b\7u\2\2\u020b"+
+    "\u020c\7g\2\2\u020c\u0099\3\2\2\2\u020d\u020e\7p\2\2\u020e\u020f\7w\2"+
+    "\2\u020f\u0210\7n\2\2\u0210\u0211\7n\2\2\u0211\u009b\3\2\2\2\u0212\u0218"+
+    "\5\u009eO\2\u0213\u0214\5\24\n\2\u0214\u0215\5\u009eO\2\u0215\u0217\3"+
+    "\2\2\2\u0216\u0213\3\2\2\2\u0217\u021a\3\2\2\2\u0218\u0216\3\2\2\2\u0218"+
+    "\u0219\3\2\2\2\u0219\u021b\3\2\2\2\u021a\u0218\3\2\2\2\u021b\u021c\6N"+
+    "\4\2\u021c\u009d\3\2\2\2\u021d\u0221\t\22\2\2\u021e\u0220\t\23\2\2\u021f"+
+    "\u021e\3\2\2\2\u0220\u0223\3\2\2\2\u0221\u021f\3\2\2\2\u0221\u0222\3\2"+
+    "\2\2\u0222\u009f\3\2\2\2\u0223\u0221\3\2\2\2\u0224\u022d\7\62\2\2\u0225"+
+    "\u0229\t\b\2\2\u0226\u0228\t\t\2\2\u0227\u0226\3\2\2\2\u0228\u022b\3\2"+
+    "\2\2\u0229\u0227\3\2\2\2\u0229\u022a\3\2\2\2\u022a\u022d\3\2\2\2\u022b"+
+    "\u0229\3\2\2\2\u022c\u0224\3\2\2\2\u022c\u0225\3\2\2\2\u022d\u022e\3\2"+
+    "\2\2\u022e\u022f\bP\4\2\u022f\u00a1\3\2\2\2\u0230\u0234\t\22\2\2\u0231"+
+    "\u0233\t\23\2\2\u0232\u0231\3\2\2\2\u0233\u0236\3\2\2\2\u0234\u0232\3"+
+    "\2\2\2\u0234\u0235\3\2\2\2\u0235\u0237\3\2\2\2\u0236\u0234\3\2\2\2\u0237"+
+    "\u0238\bQ\4\2\u0238\u00a3\3\2\2\2$\2\3\u00a7\u00b1\u00bb\u00c0\u019b\u019e"+
     "\u01a5\u01a8\u01af\u01b2\u01b5\u01bc\u01bf\u01c5\u01c7\u01cb\u01d0\u01d2"+
-    "\u01d5\u01dd\u01df\u01e9\u01eb\u01ef\u01f5\u01f7\u0212\u021b\u0223\u0226"+
-    "\u022e\5\b\2\2\4\3\2\4\2\2";
+    "\u01d5\u01dd\u01df\u01e9\u01eb\u01ef\u01f5\u01f7\u01fd\u0218\u0221\u0229"+
+    "\u022c\u0234\5\b\2\2\4\3\2\4\2\2";
   public static final ATN _ATN =
     new ATNDeserializer().deserialize(_serializedATN.toCharArray());
   static {
diff --git a/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/Walker.java b/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/Walker.java
index b1a5ed3a260..474e47599a8 100644
--- a/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/Walker.java
+++ b/modules/lang-painless/src/main/java/org/elasticsearch/painless/antlr/Walker.java
@@ -834,9 +834,12 @@ public final class Walker extends PainlessParserBaseVisitor<Object> {
 
     @Override
     public Object visitRegex(RegexContext ctx) {
-        String pattern = ctx.REGEX().getText().substring(1, ctx.REGEX().getText().length() - 1);
+        String text = ctx.REGEX().getText();
+        int lastSlash = text.lastIndexOf('/');
+        String pattern = text.substring(1, lastSlash);
+        String flags = text.substring(lastSlash + 1);
         List<ALink> links = new ArrayList<>();
-        links.add(new LRegex(location(ctx), pattern));
+        links.add(new LRegex(location(ctx), pattern, flags));
 
         return links;
     }
diff --git a/modules/lang-painless/src/main/java/org/elasticsearch/painless/node/LRegex.java b/modules/lang-painless/src/main/java/org/elasticsearch/painless/node/LRegex.java
index 720e9d45969..324b6d72cf1 100644
--- a/modules/lang-painless/src/main/java/org/elasticsearch/painless/node/LRegex.java
+++ b/modules/lang-painless/src/main/java/org/elasticsearch/painless/node/LRegex.java
@@ -35,14 +35,20 @@ import org.elasticsearch.painless.WriterConstants;
  */
 public final class LRegex extends ALink {
     private final String pattern;
+    private final int flags;
     private Constant constant;
 
-    public LRegex(Location location, String pattern) {
+    public LRegex(Location location, String pattern, String flagsString) {
         super(location, 1);
         this.pattern = pattern;
+        int flags = 0;
+        for (int c = 0; c < flagsString.length(); c++) {
+            flags |= flagForChar(flagsString.charAt(c));
+        }
+        this.flags = flags;
         try {
             // Compile the pattern early after parsing so we can throw an error to the user with the location
-            Pattern.compile(pattern);
+            Pattern.compile(pattern, flags);
         } catch (PatternSyntaxException e) {
             throw createError(e);
         }
@@ -82,6 +88,21 @@ public final class LRegex extends ALink {
 
     private void initializeConstant(MethodWriter writer) {
         writer.push(pattern);
+        writer.push(flags);
         writer.invokeStatic(Definition.PATTERN_TYPE.type, WriterConstants.PATTERN_COMPILE);
     }
+
+    private int flagForChar(char c) {
+        switch (c) {
+        case 'c': return Pattern.CANON_EQ;
+        case 'i': return Pattern.CASE_INSENSITIVE;
+        case 'l': return Pattern.LITERAL;
+        case 'm': return Pattern.MULTILINE;
+        case 's': return Pattern.DOTALL;
+        case 'U': return Pattern.UNICODE_CHARACTER_CLASS;
+        case 'u': return Pattern.UNICODE_CASE;
+        case 'x': return Pattern.COMMENTS;
+        default: throw new IllegalArgumentException("Unknown flag [" + c + "]");
+        }
+    }
 }
diff --git a/modules/lang-painless/src/main/resources/org/elasticsearch/painless/java.util.regex.txt b/modules/lang-painless/src/main/resources/org/elasticsearch/painless/java.util.regex.txt
index a8982871a33..6befc865731 100644
--- a/modules/lang-painless/src/main/resources/org/elasticsearch/painless/java.util.regex.txt
+++ b/modules/lang-painless/src/main/resources/org/elasticsearch/painless/java.util.regex.txt
@@ -25,7 +25,14 @@
 class Pattern -> java.util.regex.Pattern extends Object {
 # Pattern compile(String)   Intentionally not included. We don't want dynamic patterns because they allow regexes to be generated per time
 #                           the script is run which is super slow. LRegex generates code that calls this method but it skips these checks.
+  Predicate asPredicate()
+  int flags()
   Matcher matcher(CharSequence)
+  String pattern()
+  String quote(String)
+  String[] split(CharSequence)
+  String[] split(CharSequence,int)
+  Stream splitAsStream(CharSequence)
 }
 
 class Matcher -> java.util.regex.Matcher extends Object {
diff --git a/modules/lang-painless/src/test/java/org/elasticsearch/painless/RegexTests.java b/modules/lang-painless/src/test/java/org/elasticsearch/painless/RegexTests.java
index ee281e4656b..a36eedd7058 100644
--- a/modules/lang-painless/src/test/java/org/elasticsearch/painless/RegexTests.java
+++ b/modules/lang-painless/src/test/java/org/elasticsearch/painless/RegexTests.java
@@ -19,8 +19,12 @@
 
 package org.elasticsearch.painless;
 
+import java.util.Arrays;
+import java.util.HashSet;
+import java.util.regex.Pattern;
 import java.util.regex.PatternSyntaxException;
 
+import static java.util.Collections.emptyMap;
 import static java.util.Collections.singletonMap;
 import static org.hamcrest.Matchers.containsString;
 
@@ -125,6 +129,52 @@ public class RegexTests extends ScriptTestCase {
         assertEquals("o", exec("Matcher m = /(?<first>f)(?<second>o)o/.matcher('foo'); m.find(); return m.namedGroup('second')"));
     }
 
+    // Make sure some methods on Pattern are whitelisted
+    public void testSplit() {
+        assertArrayEquals(new String[] {"cat", "dog"}, (String[]) exec("/,/.split('cat,dog')"));
+    }
+
+    public void testSplitAsStream() {
+        assertEquals(new HashSet<>(Arrays.asList("cat", "dog")), exec("/,/.splitAsStream('cat,dog').collect(Collectors.toSet())"));
+    }
+
+    // Make sure the flags are set
+    public void testMultilineFlag() {
+        assertEquals(Pattern.MULTILINE, exec("/./m.flags()"));
+    }
+
+    public void testSinglelineFlag() {
+        assertEquals(Pattern.DOTALL, exec("/./s.flags()"));
+    }
+
+    public void testInsensitiveFlag() {
+        assertEquals(Pattern.CASE_INSENSITIVE, exec("/./i.flags()"));
+    }
+
+    public void testExtendedFlag() {
+        assertEquals(Pattern.COMMENTS, exec("/./x.flags()"));
+    }
+
+    public void testUnicodeCaseFlag() {
+        assertEquals(Pattern.UNICODE_CASE, exec("/./u.flags()"));
+    }
+
+    public void testUnicodeCharacterClassFlag() {
+        assertEquals(Pattern.UNICODE_CASE | Pattern.UNICODE_CHARACTER_CLASS, exec("/./U.flags()"));
+    }
+
+    public void testLiteralFlag() {
+        assertEquals(Pattern.LITERAL, exec("/./l.flags()"));
+    }
+
+    public void testCanonicalEquivalenceFlag() {
+        assertEquals(Pattern.CANON_EQ, exec("/./c.flags()"));
+    }
+
+    public void testManyFlags() {
+        assertEquals(Pattern.CANON_EQ | Pattern.CASE_INSENSITIVE | Pattern.UNICODE_CASE | Pattern.COMMENTS, exec("/./ciux.flags()"));
+    }
+
     public void testCantUsePatternCompile() {
         IllegalArgumentException e = expectScriptThrows(IllegalArgumentException.class, () -> {
             exec("Pattern.compile('aa')");
@@ -146,4 +196,11 @@ public class RegexTests extends ScriptTestCase {
         });
         assertEquals("Cannot cast from [int] to [String].", e.getMessage());
     }
+
+    public void testBogusRegexFlag() {
+        IllegalArgumentException e = expectScriptThrows(IllegalArgumentException.class, () -> {
+            exec("/asdf/b", emptyMap(), emptyMap(), null); // Not picky so we get a non-assertion error
+        });
+        assertEquals("invalid sequence of tokens near ['b'].", e.getMessage());
+    }
 }