diff --git a/api/integrations/launch_darkly/services.py b/api/integrations/launch_darkly/services.py
index 68d6ee0988f6..031f43deae4d 100644
--- a/api/integrations/launch_darkly/services.py
+++ b/api/integrations/launch_darkly/services.py
@@ -174,6 +174,14 @@ def _ld_operator_to_flagsmith_operator(ld_operator: str) -> Optional[ConditionOp
     }.get(ld_operator, None)
 
 
+def _to_unanchored_regex(pattern: str) -> str:
+    # Launch Darkly searches for `matches` patterns anywhere in the value, while Flagsmith matches from the
+    # start only. Leading inline flags such as `(?i)` must stay at the start of the expression.
+    flags = re.match(r"(?:\(\?[a-zA-Z]+\))+", pattern)
+    prefix = flags.group() if flags else ""
+    return f"{prefix}[\\s\\S]*(?:{pattern[len(prefix) :]})"
+
+
 def _convert_ld_values(values: list[str], ld_operator: str) -> list[str]:
     """
     Convert "values" of a Launch Darkly clause to Flagsmith compatible values. Some matching is converted to
@@ -201,6 +209,8 @@ def _convert_ld_values(values: list[str], ld_operator: str) -> list[str]:
             return [".*" + re.escape(value) + "$" for value in values]
         case "startsWith":
             return ["^" + re.escape(value) for value in values]
+        case "matches":
+            return [_to_unanchored_regex(value) for value in values]
         case "semVerEqual" | "semVerLessThan" | "semVerGreaterThan":
             return [value + ":semver" for value in values]
         case _:
diff --git a/api/tests/unit/integrations/launch_darkly/test_services.py b/api/tests/unit/integrations/launch_darkly/test_services.py
index dd76a48a0d81..df22a5ff93e8 100644
--- a/api/tests/unit/integrations/launch_darkly/test_services.py
+++ b/api/tests/unit/integrations/launch_darkly/test_services.py
@@ -395,7 +395,7 @@ def test_process_import_request__valid_segments__creates_segment_per_environment
                                 {
                                     "property": "p3",
                                     "operator": segment_constants.REGEX,
-                                    "value": "foo[0-9]{0,1}",
+                                    "value": "[\\s\\S]*(?:foo[0-9]{0,1})",
                                     "description": None,
                                 }
                             ],
@@ -511,6 +511,53 @@ def test_process_import_request__ends_with_clause__matches_suffix_only(
     assert ("Dynamic List (Override for test)" in segment_names) is expected_in_segment
 
 
+@pytest.mark.parametrize(
+    "pattern, email, expected_in_segment",
+    [
+        (r"gmail\.com", "gmail.com", True),
+        (r"gmail\.com", "user@gmail.com", True),
+        (r"gmail\.com", "user@example.org", False),
+        (r"^gmail|corp", "user@corp.com", True),
+        (r"^gmail|corp", "user@gmail.com", False),
+        (r"(?i)GMAIL\.com", "user@gmail.com", True),
+        (r"corp", "first\nuser@corp.com", True),
+        (r"^corp", "first\ncorp", False),
+    ],
+)
+@pytest.mark.django_db(transaction=True)
+def test_process_import_request__matches_clause__matches_anywhere_in_value(
+    project: Project,
+    import_request: LaunchDarklyImportRequest,
+    ld_client_mock: MagicMock,
+    pattern: str,
+    email: str,
+    expected_in_segment: bool,
+) -> None:
+    # Given
+    segments = [
+        segment
+        for segment in ld_client_mock.get_segments.return_value
+        if segment["key"] == "dynamic-list"
+    ]
+    segments[0]["rules"][0]["clauses"][0].update(op="matches", values=[pattern])
+    ld_client_mock.get_segments.return_value = segments
+    process_import_request(import_request)
+    environment = Environment.objects.get(project=project, name="Test")
+    identity = Identity.objects.create(identifier="user", environment=environment)
+    Trait.objects.create(
+        identity=identity,
+        trait_key="email",
+        value_type="unicode",
+        string_value=email,
+    )
+
+    # When
+    segment_names = {segment.name for segment in identity.get_segments()}
+
+    # Then
+    assert ("Dynamic List (Override for test)" in segment_names) is expected_in_segment
+
+
 @pytest.mark.django_db(transaction=True)
 def test_process_import_request__valid_segments__creates_identities_with_key_traits(
     project: Project,
@@ -648,7 +695,7 @@ def test_process_import_request__valid_segments__imports_correctly_x_replaced_ab
             "property", "operator", "value"
         )
     ) == {
-        ("p3", segment_constants.REGEX, "foo[0-9]{0,1}"),
+        ("p3", segment_constants.REGEX, "[\\s\\S]*(?:foo[0-9]{0,1})"),
     }
 
     # Include individual users