diff --git a/COMPAT.md b/COMPAT.md
index 213841cb1..a7baaca83 100644
--- a/COMPAT.md
+++ b/COMPAT.md
@@ -160,6 +160,10 @@ Feature support of [sqlite expr syntax](https://www.sqlite.org/lang_expr.html).
 | upper(X)                     | Yes    |         |
 | zeroblob(N)                  | Yes    |         |
 
+
+
+
+
 ### Mathematical functions
 
 | Function   | Status | Comment |
@@ -449,3 +453,16 @@ Feature support of [sqlite expr syntax](https://www.sqlite.org/lang_expr.html).
 | Variable        | No     |
 | VerifyCookie    | No     |
 | Yield           | Yes    |
+
+
+
+
+| LibSql Compatibility / Extensions|    |         |
+| ---------------------------- | ------ | ------- |
+|  **UUID**                    |        | UUID's in limbo are `blobs` by default|
+| uuid4()                      | Yes    | uuid version 4 |
+| uuid4_str()                  | Yes    | uuid v4 string alias `gen_random_uuid()` for PG compatibility|
+| uuid7(X?)                    | Yes    | uuid version 7, Optional arg for seconds since epoch|
+| uuid7_timestamp_ms(X)        | Yes    | Convert a uuid v7 to milliseconds since epoch|
+| uuid_str(X)                  | Yes    | Convert a valid uuid to string|
+| uuid_blob(X)                 | Yes    | Convert a valid uuid to blob|
diff --git a/Cargo.lock b/Cargo.lock
index 53b97bfc1..0c84456f9 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1157,6 +1157,7 @@ dependencies = [
  "sqlite3-parser",
  "tempfile",
  "thiserror 1.0.69",
+ "uuid",
 ]
 
 [[package]]
@@ -2277,6 +2278,9 @@ name = "uuid"
 version = "1.11.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f8c5f0a0af699448548ad1a2fbf920fb4bee257eae39953ba95cb84891a0446a"
+dependencies = [
+ "getrandom",
+]
 
 [[package]]
 name = "vcpkg"
diff --git a/core/Cargo.toml b/core/Cargo.toml
index 58783855a..4ef87b469 100644
--- a/core/Cargo.toml
+++ b/core/Cargo.toml
@@ -14,13 +14,14 @@ name = "limbo_core"
 path = "lib.rs"
 
 [features]
-default = ["fs", "json"]
+default = ["fs", "json", "uuid"]
 fs = []
 json = [
     "dep:jsonb",
     "dep:pest",
     "dep:pest_derive",
 ]
+uuid = ["dep:uuid"]
 
 [target.'cfg(target_os = "linux")'.dependencies]
 io-uring = "0.6.1"
@@ -54,6 +55,7 @@ pest_derive = { version = "2.0", optional = true }
 rand = "0.8.5"
 bumpalo = { version = "3.16.0", features = ["collections", "boxed"] }
 macros = { path = "../macros" }
+uuid = { version = "1.11.0", features = ["v4", "v7"], optional = true }
 
 [target.'cfg(not(target_family = "windows"))'.dev-dependencies]
 pprof = { version = "0.14.0", features = ["criterion", "flamegraph"] }
diff --git a/core/ext/mod.rs b/core/ext/mod.rs
new file mode 100644
index 000000000..312ebfcea
--- /dev/null
+++ b/core/ext/mod.rs
@@ -0,0 +1,30 @@
+#[cfg(feature = "uuid")]
+mod uuid;
+#[cfg(feature = "uuid")]
+pub use uuid::{exec_ts_from_uuid7, exec_uuid, exec_uuidblob, exec_uuidstr, UuidFunc};
+
+#[derive(Debug, Clone, PartialEq)]
+pub enum ExtFunc {
+    #[cfg(feature = "uuid")]
+    Uuid(UuidFunc),
+}
+
+impl std::fmt::Display for ExtFunc {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            #[cfg(feature = "uuid")]
+            ExtFunc::Uuid(uuidfn) => write!(f, "{}", uuidfn),
+            _ => write!(f, "unknown"),
+        }
+    }
+}
+
+impl ExtFunc {
+    pub fn resolve_function(name: &str, num_args: usize) -> Option<ExtFunc> {
+        match name {
+            #[cfg(feature = "uuid")]
+            name => UuidFunc::resolve_function(name, num_args),
+            _ => None,
+        }
+    }
+}
diff --git a/core/ext/uuid.rs b/core/ext/uuid.rs
new file mode 100644
index 000000000..00ce23d9b
--- /dev/null
+++ b/core/ext/uuid.rs
@@ -0,0 +1,341 @@
+use super::ExtFunc;
+use crate::{
+    types::{LimboText, OwnedValue},
+    LimboError,
+};
+use std::rc::Rc;
+use uuid::{ContextV7, Timestamp, Uuid};
+
+#[derive(Debug, Clone, Copy, PartialEq)]
+pub enum UuidFunc {
+    Uuid4Str,
+    Uuid4,
+    Uuid7,
+    Uuid7TS,
+    UuidStr,
+    UuidBlob,
+}
+
+impl UuidFunc {
+    pub fn resolve_function(name: &str, num_args: usize) -> Option<ExtFunc> {
+        match name {
+            "uuid4_str" => Some(ExtFunc::Uuid(UuidFunc::Uuid4Str)),
+            "uuid4" => Some(ExtFunc::Uuid(UuidFunc::Uuid4)),
+            "uuid7" if num_args < 2 => Some(ExtFunc::Uuid(UuidFunc::Uuid7)),
+            "uuid_str" if num_args == 1 => Some(ExtFunc::Uuid(UuidFunc::UuidStr)),
+            "uuid_blob" if num_args == 1 => Some(ExtFunc::Uuid(UuidFunc::UuidBlob)),
+            "uuid7_timestamp_ms" if num_args == 1 => Some(ExtFunc::Uuid(UuidFunc::Uuid7TS)),
+            // postgres_compatability
+            "gen_random_uuid" => Some(ExtFunc::Uuid(UuidFunc::Uuid4Str)),
+            _ => None,
+        }
+    }
+}
+
+impl std::fmt::Display for UuidFunc {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            UuidFunc::Uuid4Str => write!(f, "uuid4_str"),
+            UuidFunc::Uuid4 => write!(f, "uuid4"),
+            UuidFunc::Uuid7 => write!(f, "uuid7"),
+            UuidFunc::Uuid7TS => write!(f, "uuid7_timestamp_ms"),
+            UuidFunc::UuidStr => write!(f, "uuid_str"),
+            UuidFunc::UuidBlob => write!(f, "uuid_blob"),
+        }
+    }
+}
+
+pub fn exec_uuid(var: &UuidFunc, sec: Option<&OwnedValue>) -> crate::Result<OwnedValue> {
+    match var {
+        UuidFunc::Uuid4 => Ok(OwnedValue::Blob(Rc::new(
+            Uuid::new_v4().into_bytes().to_vec(),
+        ))),
+        UuidFunc::Uuid4Str => Ok(OwnedValue::Text(LimboText::new(Rc::new(
+            Uuid::new_v4().to_string(),
+        )))),
+        UuidFunc::Uuid7 => {
+            let uuid = match sec {
+                Some(OwnedValue::Integer(ref seconds)) => {
+                    let ctx = ContextV7::new();
+                    if *seconds < 0 {
+                        // not valid unix timestamp, error or null?
+                        return Ok(OwnedValue::Null);
+                    }
+                    Uuid::new_v7(Timestamp::from_unix(ctx, *seconds as u64, 0))
+                }
+                _ => Uuid::now_v7(),
+            };
+            Ok(OwnedValue::Blob(Rc::new(uuid.into_bytes().to_vec())))
+        }
+        _ => unreachable!(),
+    }
+}
+
+pub fn exec_uuidstr(reg: &OwnedValue) -> crate::Result<OwnedValue> {
+    match reg {
+        OwnedValue::Blob(blob) => {
+            let uuid = Uuid::from_slice(blob).map_err(|e| LimboError::ParseError(e.to_string()))?;
+            Ok(OwnedValue::Text(LimboText::new(Rc::new(uuid.to_string()))))
+        }
+        OwnedValue::Text(ref val) => {
+            let uuid =
+                Uuid::parse_str(&val.value).map_err(|e| LimboError::ParseError(e.to_string()))?;
+            Ok(OwnedValue::Text(LimboText::new(Rc::new(uuid.to_string()))))
+        }
+        OwnedValue::Null => Ok(OwnedValue::Null),
+        _ => Err(LimboError::ParseError(
+            "Invalid argument type for UUID function".to_string(),
+        )),
+    }
+}
+
+pub fn exec_uuidblob(reg: &OwnedValue) -> crate::Result<OwnedValue> {
+    match reg {
+        OwnedValue::Text(val) => {
+            let uuid =
+                Uuid::parse_str(&val.value).map_err(|e| LimboError::ParseError(e.to_string()))?;
+            Ok(OwnedValue::Blob(Rc::new(uuid.as_bytes().to_vec())))
+        }
+        OwnedValue::Blob(blob) => {
+            let uuid = Uuid::from_slice(blob).map_err(|e| LimboError::ParseError(e.to_string()))?;
+            Ok(OwnedValue::Blob(Rc::new(uuid.as_bytes().to_vec())))
+        }
+        OwnedValue::Null => Ok(OwnedValue::Null),
+        _ => Err(LimboError::ParseError(
+            "Invalid argument type for UUID function".to_string(),
+        )),
+    }
+}
+
+pub fn exec_ts_from_uuid7(reg: &OwnedValue) -> OwnedValue {
+    let uuid = match reg {
+        OwnedValue::Blob(blob) => {
+            Uuid::from_slice(blob).map_err(|e| LimboError::ParseError(e.to_string()))
+        }
+        OwnedValue::Text(val) => {
+            Uuid::parse_str(&val.value).map_err(|e| LimboError::ParseError(e.to_string()))
+        }
+        _ => Err(LimboError::ParseError(
+            "Invalid argument type for UUID function".to_string(),
+        )),
+    };
+    match uuid {
+        Ok(uuid) => OwnedValue::Integer(uuid_to_unix(uuid.as_bytes()) as i64),
+        // display error? sqlean seems to set value to null
+        Err(_) => OwnedValue::Null,
+    }
+}
+
+#[inline(always)]
+fn uuid_to_unix(uuid: &[u8; 16]) -> u64 {
+    ((uuid[0] as u64) << 40)
+        | ((uuid[1] as u64) << 32)
+        | ((uuid[2] as u64) << 24)
+        | ((uuid[3] as u64) << 16)
+        | ((uuid[4] as u64) << 8)
+        | (uuid[5] as u64)
+}
+
+#[cfg(test)]
+#[cfg(feature = "uuid")]
+pub mod test {
+    use super::UuidFunc;
+    use crate::types::OwnedValue;
+    #[test]
+    fn test_exec_uuid_v4blob() {
+        use super::exec_uuid;
+        use uuid::Uuid;
+        let func = UuidFunc::Uuid4;
+        let owned_val = exec_uuid(&func, None);
+        match owned_val {
+            Ok(OwnedValue::Blob(blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(&blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 4);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v4str() {
+        use super::{exec_uuid, UuidFunc};
+        use uuid::Uuid;
+        let func = UuidFunc::Uuid4Str;
+        let owned_val = exec_uuid(&func, None);
+        match owned_val {
+            Ok(OwnedValue::Text(v4str)) => {
+                assert_eq!(v4str.value.len(), 36);
+                let uuid = Uuid::parse_str(&v4str.value);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 4);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v7_now() {
+        use super::{exec_uuid, UuidFunc};
+        use uuid::Uuid;
+        let func = UuidFunc::Uuid7;
+        let owned_val = exec_uuid(&func, None);
+        match owned_val {
+            Ok(OwnedValue::Blob(blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(&blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 7);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v7_with_input() {
+        use super::{exec_uuid, UuidFunc};
+        use uuid::Uuid;
+        let func = UuidFunc::Uuid7;
+        let owned_val = exec_uuid(&func, Some(&OwnedValue::Integer(946702800)));
+        match owned_val {
+            Ok(OwnedValue::Blob(blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(&blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 7);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v7_now_to_timestamp() {
+        use super::{exec_ts_from_uuid7, exec_uuid, UuidFunc};
+        use uuid::Uuid;
+        let func = UuidFunc::Uuid7;
+        let owned_val = exec_uuid(&func, None);
+        match owned_val {
+            Ok(OwnedValue::Blob(ref blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 7);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+        let result = exec_ts_from_uuid7(&owned_val.expect("uuid7"));
+        if let OwnedValue::Integer(ref ts) = result {
+            let unixnow = (std::time::SystemTime::now()
+                .duration_since(std::time::UNIX_EPOCH)
+                .unwrap()
+                .as_secs()
+                * 1000) as i64;
+            assert!(*ts >= unixnow - 1000);
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v7_to_timestamp() {
+        use super::{exec_ts_from_uuid7, exec_uuid, UuidFunc};
+        use uuid::Uuid;
+        let func = UuidFunc::Uuid7;
+        let owned_val = exec_uuid(&func, Some(&OwnedValue::Integer(946702800)));
+        match owned_val {
+            Ok(OwnedValue::Blob(ref blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 7);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+        let result = exec_ts_from_uuid7(&owned_val.expect("uuid7"));
+        assert_eq!(result, OwnedValue::Integer(946702800 * 1000));
+        if let OwnedValue::Integer(ts) = result {
+            let time = chrono::DateTime::from_timestamp(ts / 1000, 0);
+            assert_eq!(
+                time.unwrap(),
+                "2000-01-01T05:00:00Z"
+                    .parse::<chrono::DateTime<chrono::Utc>>()
+                    .unwrap()
+            );
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v4_str_to_blob() {
+        use super::{exec_uuid, exec_uuidblob, UuidFunc};
+        use uuid::Uuid;
+        let owned_val = exec_uuidblob(
+            &exec_uuid(&UuidFunc::Uuid4Str, None).expect("uuid v4 string to generate"),
+        );
+        match owned_val {
+            Ok(OwnedValue::Blob(blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(&blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 4);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v7_str_to_blob() {
+        use super::{exec_uuid, exec_uuidblob, exec_uuidstr, UuidFunc};
+        use uuid::Uuid;
+        // convert a v7 blob to a string then back to a blob
+        let owned_val = exec_uuidblob(
+            &exec_uuidstr(&exec_uuid(&UuidFunc::Uuid7, None).expect("uuid v7 blob to generate"))
+                .expect("uuid v7 string to generate"),
+        );
+        match owned_val {
+            Ok(OwnedValue::Blob(blob)) => {
+                assert_eq!(blob.len(), 16);
+                let uuid = Uuid::from_slice(&blob);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 7);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v4_blob_to_str() {
+        use super::{exec_uuid, exec_uuidstr, UuidFunc};
+        use uuid::Uuid;
+        // convert a v4 blob to a string
+        let owned_val =
+            exec_uuidstr(&exec_uuid(&UuidFunc::Uuid4, None).expect("uuid v7 blob to generate"));
+        match owned_val {
+            Ok(OwnedValue::Text(v4str)) => {
+                assert_eq!(v4str.value.len(), 36);
+                let uuid = Uuid::parse_str(&v4str.value);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 4);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+
+    #[test]
+    fn test_exec_uuid_v7_blob_to_str() {
+        use super::{exec_uuid, exec_uuidstr};
+        use uuid::Uuid;
+        // convert a v7 blob to a string
+        let owned_val = exec_uuidstr(
+            &exec_uuid(&UuidFunc::Uuid7, Some(&OwnedValue::Integer(123456789)))
+                .expect("uuid v7 blob to generate"),
+        );
+        match owned_val {
+            Ok(OwnedValue::Text(v7str)) => {
+                assert_eq!(v7str.value.len(), 36);
+                let uuid = Uuid::parse_str(&v7str.value);
+                assert!(uuid.is_ok());
+                assert_eq!(uuid.unwrap().get_version_num(), 7);
+            }
+            _ => panic!("exec_uuid did not return a Blob variant"),
+        }
+    }
+}
diff --git a/core/function.rs b/core/function.rs
index 86c88a1e4..8681a4fdf 100644
--- a/core/function.rs
+++ b/core/function.rs
@@ -1,6 +1,6 @@
+use crate::ext::ExtFunc;
 use std::fmt;
 use std::fmt::Display;
-
 #[cfg(feature = "json")]
 #[derive(Debug, Clone, PartialEq)]
 pub enum JsonFunc {
@@ -256,13 +256,14 @@ impl Display for MathFunc {
     }
 }
 
-#[derive(Debug)]
+#[derive(Debug, Clone, PartialEq)]
 pub enum Func {
     Agg(AggFunc),
     Scalar(ScalarFunc),
     Math(MathFunc),
     #[cfg(feature = "json")]
     Json(JsonFunc),
+    Extension(ExtFunc),
 }
 
 impl Display for Func {
@@ -273,6 +274,7 @@ impl Display for Func {
             Func::Math(math_func) => write!(f, "{}", math_func),
             #[cfg(feature = "json")]
             Func::Json(json_func) => write!(f, "{}", json_func),
+            Func::Extension(ext_func) => write!(f, "{}", ext_func),
         }
     }
 }
@@ -366,7 +368,10 @@ impl Func {
             "tan" => Ok(Func::Math(MathFunc::Tan)),
             "tanh" => Ok(Func::Math(MathFunc::Tanh)),
             "trunc" => Ok(Func::Math(MathFunc::Trunc)),
-            _ => Err(()),
+            _ => match ExtFunc::resolve_function(name, arg_count) {
+                Some(ext_func) => Ok(Func::Extension(ext_func)),
+                None => Err(()),
+            },
         }
     }
 }
diff --git a/core/io/generic.rs b/core/io/generic.rs
index 0c35eaf52..17f51d792 100644
--- a/core/io/generic.rs
+++ b/core/io/generic.rs
@@ -15,7 +15,11 @@ impl GenericIO {
 impl IO for GenericIO {
     fn open_file(&self, path: &str, flags: OpenFlags, _direct: bool) -> Result<Rc<dyn File>> {
         trace!("open_file(path = {})", path);
-        let file = std::fs::File::open(path)?;
+        let file = std::fs::OpenOptions::new()
+            .read(true)
+            .write(true)
+            .create(matches!(flags, OpenFlags::Create))
+            .open(path)?;
         Ok(Rc::new(GenericFile {
             file: RefCell::new(file),
         }))
diff --git a/core/lib.rs b/core/lib.rs
index f49d8bd3b..a5044fc9a 100644
--- a/core/lib.rs
+++ b/core/lib.rs
@@ -1,4 +1,5 @@
 mod error;
+mod ext;
 mod function;
 mod io;
 #[cfg(feature = "json")]
diff --git a/core/translate/expr.rs b/core/translate/expr.rs
index 363d96a99..734dbb98e 100644
--- a/core/translate/expr.rs
+++ b/core/translate/expr.rs
@@ -1,10 +1,12 @@
 use sqlite3_parser::ast::{self, UnaryOperator};
 
+#[cfg(feature = "uuid")]
+use crate::ext::{ExtFunc, UuidFunc};
 #[cfg(feature = "json")]
 use crate::function::JsonFunc;
 use crate::function::{AggFunc, Func, FuncCtx, MathFuncArity, ScalarFunc};
 use crate::schema::Type;
-use crate::util::normalize_ident;
+use crate::util::{exprs_are_equivalent, normalize_ident};
 use crate::vdbe::{builder::ProgramBuilder, BranchOffset, Insn};
 use crate::Result;
 
@@ -554,10 +556,7 @@ pub fn translate_expr(
 ) -> Result<usize> {
     if let Some(precomputed_exprs_to_registers) = precomputed_exprs_to_registers {
         for (precomputed_expr, reg) in precomputed_exprs_to_registers.iter() {
-            // TODO: implement a custom equality check for expressions
-            // there are lots of examples where this breaks, even simple ones like
-            // sum(x) != SUM(x)
-            if expr == *precomputed_expr {
+            if exprs_are_equivalent(expr, precomputed_expr) {
                 program.emit_insn(Insn::Copy {
                     src_reg: *reg,
                     dst_reg: target_register,
@@ -1613,6 +1612,92 @@ pub fn translate_expr(
                         }
                     }
                 }
+                Func::Extension(ext_func) => match ext_func {
+                    #[cfg(feature = "uuid")]
+                    ExtFunc::Uuid(ref uuid_fn) => match uuid_fn {
+                        UuidFunc::UuidStr | UuidFunc::UuidBlob | UuidFunc::Uuid7TS => {
+                            let args = if let Some(args) = args {
+                                if args.len() != 1 {
+                                    crate::bail_parse_error!(
+                                        "{} function with not exactly 1 argument",
+                                        ext_func.to_string()
+                                    );
+                                }
+                                args
+                            } else {
+                                crate::bail_parse_error!(
+                                    "{} function with no arguments",
+                                    ext_func.to_string()
+                                );
+                            };
+
+                            let regs = program.alloc_register();
+                            translate_expr(
+                                program,
+                                referenced_tables,
+                                &args[0],
+                                regs,
+                                precomputed_exprs_to_registers,
+                            )?;
+                            program.emit_insn(Insn::Function {
+                                constant_mask: 0,
+                                start_reg: regs,
+                                dest: target_register,
+                                func: func_ctx,
+                            });
+                            Ok(target_register)
+                        }
+                        UuidFunc::Uuid4 | UuidFunc::Uuid4Str => {
+                            if args.is_some() {
+                                crate::bail_parse_error!(
+                                    "{} function with arguments",
+                                    ext_func.to_string()
+                                );
+                            }
+                            let regs = program.alloc_register();
+                            program.emit_insn(Insn::Function {
+                                constant_mask: 0,
+                                start_reg: regs,
+                                dest: target_register,
+                                func: func_ctx,
+                            });
+                            Ok(target_register)
+                        }
+                        UuidFunc::Uuid7 => {
+                            let args = match args {
+                                Some(args) if args.len() > 1 => crate::bail_parse_error!(
+                                    "{} function with more than 1 argument",
+                                    ext_func.to_string()
+                                ),
+                                Some(args) => args,
+                                None => &vec![],
+                            };
+                            let mut start_reg = None;
+                            if let Some(arg) = args.first() {
+                                let reg = program.alloc_register();
+                                start_reg = Some(reg);
+                                translate_expr(
+                                    program,
+                                    referenced_tables,
+                                    arg,
+                                    reg,
+                                    precomputed_exprs_to_registers,
+                                )?;
+                                if let ast::Expr::Literal(_) = arg {
+                                    program.mark_last_insn_constant()
+                                }
+                            }
+                            program.emit_insn(Insn::Function {
+                                constant_mask: 0,
+                                start_reg: start_reg.unwrap_or(target_register),
+                                dest: target_register,
+                                func: func_ctx,
+                            });
+                            Ok(target_register)
+                        }
+                    },
+                    _ => unreachable!("{ext_func} not implemented yet"),
+                },
                 Func::Math(math_func) => match math_func.arity() {
                     MathFuncArity::Nullary => {
                         if args.is_some() {
diff --git a/core/translate/planner.rs b/core/translate/planner.rs
index 8a20a4029..8ca09efe6 100644
--- a/core/translate/planner.rs
+++ b/core/translate/planner.rs
@@ -2,10 +2,13 @@ use super::plan::{
     Aggregate, BTreeTableReference, DeletePlan, Direction, GroupBy, Plan, ResultSetColumn,
     SelectPlan, SourceOperator,
 };
-use crate::{bail_parse_error, function::Func, schema::Schema, util::normalize_ident, Result};
-use sqlite3_parser::ast::{
-    self, Expr, FromClause, JoinType, Limit, QualifiedName, ResultColumn, SortedColumn,
+use crate::{
+    function::Func,
+    schema::Schema,
+    util::{exprs_are_equivalent, normalize_ident},
+    Result,
 };
+use sqlite3_parser::ast::{self, Expr, FromClause, JoinType, Limit, QualifiedName, ResultColumn};
 
 pub struct OperatorIdCounter {
     id: usize,
@@ -23,7 +26,10 @@ impl OperatorIdCounter {
 }
 
 fn resolve_aggregates(expr: &ast::Expr, aggs: &mut Vec<Aggregate>) -> bool {
-    if aggs.iter().any(|a| a.original_expr == *expr) {
+    if aggs
+        .iter()
+        .any(|a| exprs_are_equivalent(&a.original_expr, expr))
+    {
         return true;
     }
     match expr {
diff --git a/core/vdbe/mod.rs b/core/vdbe/mod.rs
index 26f125675..0ab196afc 100644
--- a/core/vdbe/mod.rs
+++ b/core/vdbe/mod.rs
@@ -24,6 +24,8 @@ pub mod sorter;
 mod datetime;
 
 use crate::error::{LimboError, SQLITE_CONSTRAINT_PRIMARYKEY};
+#[cfg(feature = "uuid")]
+use crate::ext::{exec_ts_from_uuid7, exec_uuid, exec_uuidblob, exec_uuidstr, ExtFunc, UuidFunc};
 use crate::function::{AggFunc, FuncCtx, MathFunc, MathFuncArity, ScalarFunc};
 use crate::pseudo::PseudoCursor;
 use crate::schema::Table;
@@ -37,42 +39,23 @@ use crate::util::parse_schema_rows;
 use crate::{function::JsonFunc, json::get_json, json::json_array};
 use crate::{Connection, Result, TransactionState};
 use crate::{Rows, DATABASE_VERSION};
+use macros::Description;
 
 use datetime::{exec_date, exec_time, exec_unixepoch};
 
 use rand::distributions::{Distribution, Uniform};
 use rand::{thread_rng, Rng};
 use regex::Regex;
-use std::borrow::BorrowMut;
+use std::borrow::{Borrow, BorrowMut};
 use std::cell::RefCell;
 use std::collections::{BTreeMap, HashMap};
-use std::fmt::Display;
 use std::rc::{Rc, Weak};
+
 pub type BranchOffset = i64;
-use macros::Description;
 pub type CursorID = usize;
 
 pub type PageIdx = usize;
 
-#[allow(dead_code)]
-#[derive(Debug)]
-pub enum Func {
-    Scalar(ScalarFunc),
-    #[cfg(feature = "json")]
-    Json(JsonFunc),
-}
-
-impl Display for Func {
-    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        let str = match self {
-            Func::Scalar(scalar_func) => scalar_func.to_string(),
-            #[cfg(feature = "json")]
-            Func::Json(json_func) => json_func.to_string(),
-        };
-        write!(f, "{}", str)
-    }
-}
-
 #[derive(Description, Debug)]
 pub enum Insn {
     // Initialize the program state and jump to the given PC.
@@ -2539,6 +2522,38 @@ impl Program {
                                 state.registers[*dest] = exec_replace(source, pattern, replacement);
                             }
                         },
+                        crate::function::Func::Extension(extfn) => match extfn {
+                            #[cfg(feature = "uuid")]
+                            ExtFunc::Uuid(uuidfn) => match uuidfn {
+                                UuidFunc::Uuid4 | UuidFunc::Uuid4Str => {
+                                    state.registers[*dest] = exec_uuid(uuidfn, None)?
+                                }
+                                UuidFunc::Uuid7 => match arg_count {
+                                    0 => {
+                                        state.registers[*dest] =
+                                            exec_uuid(uuidfn, None).unwrap_or(OwnedValue::Null);
+                                    }
+                                    1 => {
+                                        let reg_value = state.registers[*start_reg].borrow();
+                                        state.registers[*dest] = exec_uuid(uuidfn, Some(reg_value))
+                                            .unwrap_or(OwnedValue::Null);
+                                    }
+                                    _ => unreachable!(),
+                                },
+                                _ => {
+                                    // remaining accept 1 arg
+                                    let reg_value = state.registers[*start_reg].borrow();
+                                    state.registers[*dest] = match uuidfn {
+                                        UuidFunc::Uuid7TS => Some(exec_ts_from_uuid7(reg_value)),
+                                        UuidFunc::UuidStr => exec_uuidstr(reg_value).ok(),
+                                        UuidFunc::UuidBlob => exec_uuidblob(reg_value).ok(),
+                                        _ => unreachable!(),
+                                    }
+                                    .unwrap_or(OwnedValue::Null);
+                                }
+                            },
+                            _ => unreachable!(), // when more extension types are added
+                        },
                         crate::function::Func::Math(math_func) => match math_func.arity() {
                             MathFuncArity::Nullary => match math_func {
                                 MathFunc::Pi => {