diff --git a/changelog.d/1855.fix.md b/changelog.d/1855.fix.md
new file mode 100644
index 0000000000..78507a8a04
--- /dev/null
+++ b/changelog.d/1855.fix.md
@@ -0,0 +1,3 @@
+Fixed `datadog_filter` wildcard matching failing on values containing newlines. Wildcard patterns (e.g. `field:*`, `field:*some*`) compiled to regexes where `.` could not match `\n`, so values with a trailing newline (common in Lambda, container stdout, and other line-delimited sources) or embedded newlines never matched. Wildcards now match across newlines.
+
+authors: Stunned1
diff --git a/src/datadog/filter/regex.rs b/src/datadog/filter/regex.rs
index dce76807d9..3f77b267f8 100644
--- a/src/datadog/filter/regex.rs
+++ b/src/datadog/filter/regex.rs
@@ -2,13 +2,16 @@ use regex::Regex;
 
 /// Returns compiled word boundary regex.
 ///
+/// The `(?s)` flag makes `.` match any character including `\n`, so that
+/// wildcards (`*`) match across newlines in multi-line values.
+///
 /// # Panics
 /// Panics if an invalid wildcard regex is provided.
 #[allow(clippy::module_name_repetitions)] // Renaming is a breaking change.
 #[must_use]
 pub fn word_regex(to_match: &str) -> Regex {
     Regex::new(&format!(
-        r"\b{}\b",
+        r"(?s)\b{}\b",
         regex::escape(to_match).replace("\\*", ".*")
     ))
     .expect("invalid wildcard regex")
@@ -16,14 +19,52 @@ pub fn word_regex(to_match: &str) -> Regex {
 
 /// Returns compiled wildcard regex.
 ///
+/// The `(?s)` flag makes `.` match any character including `\n`, so that
+/// wildcards (`*`) match values with trailing or embedded newlines.
+///
 /// # Panics
 /// Panics if an invalid wildcard regex is provided.
 #[allow(clippy::module_name_repetitions)] // Renaming is a breaking change.
 #[must_use]
 pub fn wildcard_regex(to_match: &str) -> Regex {
     Regex::new(&format!(
-        "^{}$",
+        "(?s)^{}$",
         regex::escape(to_match).replace("\\*", ".*")
     ))
     .expect("invalid wildcard regex")
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn wildcard_matches_trailing_newline() {
+        assert!(wildcard_regex("*").is_match("hello world\n"));
+        assert!(wildcard_regex("*some*").is_match("here is some content\n"));
+        assert!(wildcard_regex("hello*").is_match("hello world\n"));
+    }
+
+    #[test]
+    fn wildcard_matches_embedded_newline() {
+        assert!(wildcard_regex("*").is_match("line1\nline2"));
+        assert!(wildcard_regex("*line2").is_match("line1\nline2"));
+        assert!(wildcard_regex("a*b").is_match("a\nb"));
+    }
+
+    #[test]
+    fn wildcard_does_not_over_match() {
+        // No wildcard at the end: the value must end with the literal.
+        assert!(!wildcard_regex("*some").is_match("here is some\n"));
+        // Exact patterns still require exact matches.
+        assert!(wildcard_regex("abc").is_match("abc"));
+        assert!(!wildcard_regex("abc").is_match("abc\n"));
+    }
+
+    #[test]
+    fn word_matches_across_newline() {
+        assert!(word_regex("foo*bar").is_match("foo\nbar"));
+        assert!(word_regex("*some*").is_match("has some stuff\n"));
+        assert!(!word_regex("foo*bar").is_match("foo\nbaz"));
+    }
+}
diff --git a/src/stdlib/match_datadog_query.rs b/src/stdlib/match_datadog_query.rs
index e527a40440..6713028758 100644
--- a/src/stdlib/match_datadog_query.rs
+++ b/src/stdlib/match_datadog_query.rs
@@ -1060,6 +1060,42 @@ mod test {
             tdef: type_def(),
         }
 
+        wildcard_facet_trailing_newline {
+            args: func_args![value: value!({"a": "hello world\n"}), query: "@a:*"],
+            want: Ok(true),
+            tdef: type_def(),
+        }
+
+        wildcard_contains_facet_trailing_newline {
+            args: func_args![value: value!({"a": "here is some content\n"}), query: "@a:*some*"],
+            want: Ok(true),
+            tdef: type_def(),
+        }
+
+        wildcard_suffix_facet_trailing_newline {
+            args: func_args![value: value!({"a": "hello world\n"}), query: "@a:hello*"],
+            want: Ok(true),
+            tdef: type_def(),
+        }
+
+        wildcard_prefix_facet_trailing_newline_no_match {
+            args: func_args![value: value!({"a": "here is some\n"}), query: "@a:*some"],
+            want: Ok(false),
+            tdef: type_def(),
+        }
+
+        wildcard_facet_multiline {
+            args: func_args![value: value!({"a": "line1\nline2"}), query: "@a:*line2"],
+            want: Ok(true),
+            tdef: type_def(),
+        }
+
+        wildcard_message_multiline {
+            args: func_args![value: value!({"message": "foo\nbar"}), query: "foo*bar"],
+            want: Ok(true),
+            tdef: type_def(),
+        }
+
         range_message_unbounded {
             args: func_args![value: value!({"message": "1"}), query: "[* TO *]"],
             want: Ok(true),