diff --git a/Lib/sre_parse.py b/Lib/sre_parse.py
index ab37fd3fe2f..d8d1bd552fb 100644
--- a/Lib/sre_parse.py
+++ b/Lib/sre_parse.py
@@ -412,7 +412,7 @@ def _parse_sub(source, state, verbose, nested=True):
     sourcematch = source.match
     start = source.tell()
     while True:
-        itemsappend(_parse(source, state, verbose))
+        itemsappend(_parse(source, state, verbose, not nested and not items))
         if not sourcematch("|"):
             break
 
@@ -466,7 +466,7 @@ def _parse_sub_cond(source, state, condgroup, verbose):
     subpattern.append((GROUPREF_EXISTS, (condgroup, item_yes, item_no)))
     return subpattern
 
-def _parse(source, state, verbose):
+def _parse(source, state, verbose, first=False):
     # parse a simple pattern
     subpattern = SubPattern(state)
 
@@ -730,10 +730,9 @@ def _parse(source, state, verbose):
                     state.checklookbehindgroup(condgroup, source)
                 elif char in FLAGS or char == "-":
                     # flags
-                    pos = source.pos
                     flags = _parse_flags(source, state, char)
                     if flags is None:  # global flags
-                        if pos != 3:  # "(?x"
+                        if not first or subpattern:
                             import warnings
                             warnings.warn(
                                 'Flags not at the start of the expression %s%s' % (
@@ -742,6 +741,8 @@ def _parse(source, state, verbose):
                                 ),
                                 DeprecationWarning, stacklevel=7
                             )
+                        if (state.flags & SRE_FLAG_VERBOSE) and not verbose:
+                            raise Verbose
                         continue
                     add_flags, del_flags = flags
                     group = None
@@ -795,9 +796,6 @@ def _parse_flags(source, state, char):
                 msg = "unknown flag" if char.isalpha() else "missing -, : or )"
                 raise source.error(msg, len(char))
     if char == ")":
-        if ((add_flags & SRE_FLAG_VERBOSE) and
-            not (state.flags & SRE_FLAG_VERBOSE)):
-            raise Verbose
         state.flags |= add_flags
         return None
     if add_flags & GLOBAL_FLAGS:
diff --git a/Lib/test/test_re.py b/Lib/test/test_re.py
index 3129f7e9888..4d71eea517e 100644
--- a/Lib/test/test_re.py
+++ b/Lib/test/test_re.py
@@ -1325,32 +1325,43 @@ class ReTests(unittest.TestCase):
         upper_char = '\u1ea0' # Latin Capital Letter A with Dot Below
         lower_char = '\u1ea1' # Latin Small Letter A with Dot Below
 
-        p = re.compile(upper_char, re.I | re.U)
-        q = p.match(lower_char)
+        p = re.compile('.' + upper_char, re.I | re.S)
+        q = p.match('\n' + lower_char)
         self.assertTrue(q)
 
-        p = re.compile(lower_char, re.I | re.U)
-        q = p.match(upper_char)
+        p = re.compile('.' + lower_char, re.I | re.S)
+        q = p.match('\n' + upper_char)
         self.assertTrue(q)
 
-        p = re.compile('(?i)' + upper_char, re.U)
-        q = p.match(lower_char)
+        p = re.compile('(?i).' + upper_char, re.S)
+        q = p.match('\n' + lower_char)
         self.assertTrue(q)
 
-        p = re.compile('(?i)' + lower_char, re.U)
-        q = p.match(upper_char)
+        p = re.compile('(?i).' + lower_char, re.S)
+        q = p.match('\n' + upper_char)
         self.assertTrue(q)
 
-        p = re.compile('(?iu)' + upper_char)
-        q = p.match(lower_char)
+        p = re.compile('(?is).' + upper_char)
+        q = p.match('\n' + lower_char)
         self.assertTrue(q)
 
-        p = re.compile('(?iu)' + lower_char)
-        q = p.match(upper_char)
+        p = re.compile('(?is).' + lower_char)
+        q = p.match('\n' + upper_char)
         self.assertTrue(q)
 
-        self.assertTrue(re.match('(?ixu) ' + upper_char, lower_char))
-        self.assertTrue(re.match('(?ixu) ' + lower_char, upper_char))
+        p = re.compile('(?s)(?i).' + upper_char)
+        q = p.match('\n' + lower_char)
+        self.assertTrue(q)
+
+        p = re.compile('(?s)(?i).' + lower_char)
+        q = p.match('\n' + upper_char)
+        self.assertTrue(q)
+
+        self.assertTrue(re.match('(?ix) ' + upper_char, lower_char))
+        self.assertTrue(re.match('(?ix) ' + lower_char, upper_char))
+        self.assertTrue(re.match(' (?i) ' + upper_char, lower_char, re.X))
+        self.assertTrue(re.match('(?x) (?i) ' + upper_char, lower_char))
+        self.assertTrue(re.match(' (?x) (?i) ' + upper_char, lower_char, re.X))
 
         p = upper_char + '(?i)'
         with self.assertWarns(DeprecationWarning) as warns:
@@ -1368,6 +1379,26 @@ class ReTests(unittest.TestCase):
             'Flags not at the start of the expression %s (truncated)' % p[:20]
         )
 
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.match('(?s).(?i)' + upper_char, '\n' + lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.match('(?i) ' + upper_char + ' (?x)', lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.match(' (?x) (?i) ' + upper_char, lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.match('^(?i)' + upper_char, lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.match('$|(?i)' + upper_char, lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.match('(?:(?i)' + upper_char + ')', lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.fullmatch('(^)?(?(1)(?i)' + upper_char + ')',
+                                         lower_char))
+        with self.assertWarns(DeprecationWarning):
+            self.assertTrue(re.fullmatch('($)?(?(1)|(?i)' + upper_char + ')',
+                                         lower_char))
+
+
     def test_dollar_matches_twice(self):
         "$ matches the end of string, and just before the terminating \n"
         pattern = re.compile('$')
diff --git a/Misc/NEWS b/Misc/NEWS
index 7a79521efd7..997a03411de 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -320,6 +320,12 @@ Extension Modules
 Library
 -------
 
+- bpo-30298: Weaken the condition of deprecation warnings for inline modifiers.
+  Now allowed several subsequential inline modifiers at the start of the
+  pattern (e.g. ``'(?i)(?s)...'``).  In verbose mode whitespaces and comments
+  now are allowed before and between inline modifiers (e.g.
+  ``'(?x) (?i) (?s)...'``).
+
 - bpo-30285: Optimized case-insensitive matching and searching of regular
   expressions.