diff --git a/Cargo.lock b/Cargo.lock
index c026864907d..beb86b22404 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -7563,6 +7563,7 @@ dependencies = [
  "libsqlite3-sys",
  "log",
  "percent-encoding",
+ "regex",
  "serde",
  "serde_urlencoded",
  "sqlx-core",
diff --git a/chromadb/test/property/test_filtering.py b/chromadb/test/property/test_filtering.py
index 8fc80969c6b..fb8336ee4f1 100644
--- a/chromadb/test/property/test_filtering.py
+++ b/chromadb/test/property/test_filtering.py
@@ -6,6 +6,7 @@
 from chromadb.test.property import invariants
 from chromadb.api.types import (
     Document,
+    Documents,
     Embedding,
     Embeddings,
     GetResult,
@@ -566,3 +567,33 @@ def test_query_ids_filter_property(
     # Also check that the number of results is reasonable
     assert len(result_ids) <= n_results
     assert len(result_ids) <= len(filter_ids_set)
+
+
+def test_regex(client: ClientAPI) -> None:
+    """Tests that regex works"""
+
+    reset(client)
+    coll = client.create_collection(name="test")
+
+    test_ids: IDs = ["1", "2", "3"]
+    test_documents: Documents = ["cat", "Cat", "CAT"]
+    test_embeddings: Embeddings = [np.array([1, 1]), np.array([2, 2]), np.array([3, 3])]
+    test_metadatas: Metadatas = [{"test": 10}, {"test": 20}, {"test": 30}]
+
+    coll.add(
+        ids=test_ids,
+        documents=test_documents,
+        embeddings=test_embeddings,
+        metadatas=test_metadatas,
+    )
+
+    res = coll.get(where_document={"$regex": "cat"})
+    assert res["ids"] == ["1"]
+
+    res = coll.get(where_document={"$regex": "(?i)cat"})
+    assert sorted(res["ids"]) == ["1", "2", "3"]
+
+    res = coll.get(
+        where={"test": {"$ne": 10}}, where_document={"$regex": "(?i)c(?-i)at"}  # type: ignore[dict-item]
+    )
+    assert res["ids"] == ["2"]
diff --git a/rust/segment/src/sqlite_metadata.rs b/rust/segment/src/sqlite_metadata.rs
index 527e8884e22..c5f630a0d9e 100644
--- a/rust/segment/src/sqlite_metadata.rs
+++ b/rust/segment/src/sqlite_metadata.rs
@@ -523,16 +523,27 @@ impl IntoSqliteExpr for DocumentExpression {
         let subq = Query::select()
             .column(EmbeddingFulltextSearch::Rowid)
             .from(EmbeddingFulltextSearch::Table)
-            .and_where(
-                Expr::col(EmbeddingFulltextSearch::StringValue)
-                    .like(format!("%{}%", self.pattern.replace("%", ""))),
-            )
+            .and_where(match self.operator {
+                DocumentOperator::Contains | DocumentOperator::NotContains => {
+                    Expr::col(EmbeddingFulltextSearch::StringValue)
+                        .like(format!("%{}%", self.pattern.replace("%", "")))
+                }
+                DocumentOperator::Regex | DocumentOperator::NotRegex => Expr::cust_with_exprs(
+                    "? REGEXP ?",
+                    [
+                        Expr::col(EmbeddingFulltextSearch::StringValue).into(),
+                        Expr::value(&self.pattern),
+                    ],
+                ),
+            })
             .to_owned();
         match self.operator {
-            DocumentOperator::Contains => Expr::col((Embeddings::Table, Embeddings::Id)).in_subquery(subq),
-            DocumentOperator::NotContains => Expr::col((Embeddings::Table, Embeddings::Id)).not_in_subquery(subq),
-            DocumentOperator::Regex => todo!("Implement Regex matching. The result must be a not-nullable boolean (use `<expr>.is(true)`)"),
-            DocumentOperator::NotRegex => todo!("Implement negated Regex matching. This must be exact opposite of Regex matching (use `<expr>.not()`)"),
+            DocumentOperator::Contains | DocumentOperator::Regex => {
+                Expr::col((Embeddings::Table, Embeddings::Id)).in_subquery(subq)
+            }
+            DocumentOperator::NotContains | DocumentOperator::NotRegex => {
+                Expr::col((Embeddings::Table, Embeddings::Id)).not_in_subquery(subq)
+            }
         }
     }
 }
diff --git a/rust/sqlite/Cargo.toml b/rust/sqlite/Cargo.toml
index 6ca50a4fb6c..319d5f4a2ef 100644
--- a/rust/sqlite/Cargo.toml
+++ b/rust/sqlite/Cargo.toml
@@ -9,7 +9,7 @@ regex = { workspace = true }
 sea-query = { workspace = true, features = ["derive"] }
 sea-query-binder = { workspace = true, features = ["sqlx-sqlite"] }
 sha2 = { workspace = true }
-sqlx = { workspace = true }
+sqlx = { workspace = true, features = ["regexp"] }
 tempfile = { workspace = true }
 pyo3 = { workspace = true, optional = true }
 thiserror = { workspace = true }
@@ -22,4 +22,3 @@ rust-embed = { workspace = true }
 chroma-error = { workspace = true, features = ["sqlx"] }
 chroma-types = { workspace = true }
 chroma-config = { workspace = true }
-
diff --git a/rust/sqlite/src/config.rs b/rust/sqlite/src/config.rs
index abb8b142919..baaf753c236 100644
--- a/rust/sqlite/src/config.rs
+++ b/rust/sqlite/src/config.rs
@@ -104,7 +104,8 @@ impl Configurable<SqliteDBConfig, SqliteCreationError> for SqliteDb {
             // we turn it off
             .pragma("foreign_keys", "OFF")
             .pragma("case_sensitive_like", "ON")
-            .busy_timeout(Duration::from_secs(1000));
+            .busy_timeout(Duration::from_secs(1000))
+            .with_regexp();
         let conn = if let Some(url) = &config.url {
             let path = Path::new(url);
             if let Some(parent) = path.parent() {