diff --git a/Cargo.lock b/Cargo.lock
index 3ecf6d76f..121173949 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -101,7 +101,7 @@ checksum = "061a7acccaa286c011ddc30970520b98fa40e00c9d644633fb26b5fc63a265e3"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -135,7 +135,7 @@ dependencies = [
  "proc-macro-error",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -147,7 +147,7 @@ dependencies = [
  "proc-macro-error",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -560,7 +560,7 @@ dependencies = [
  "proc-macro-error",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -898,7 +898,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ccc0a48a9b826acdf4028595adc9db92caea352f7af011a3034acd172a52a0aa"
 dependencies = [
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -961,7 +961,7 @@ checksum = "4fb810d30a7c1953f91334de7244731fc3f3c10d7fe163338a35b9f640960321"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -1297,7 +1297,7 @@ dependencies = [
  "reqwest",
  "serde",
  "serde_json",
- "syn",
+ "syn 1.0.103",
  "tempfile",
  "toml",
  "url",
@@ -1314,7 +1314,7 @@ dependencies = [
  "proc-macro2",
  "quote",
  "serde_json",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -1342,7 +1342,7 @@ dependencies = [
  "serde",
  "serde_json",
  "strum",
- "syn",
+ "syn 1.0.103",
  "thiserror",
  "tiny-keccak",
  "unicode-xid",
@@ -1357,7 +1357,7 @@ dependencies = [
  "hex",
  "quote",
  "serde_json",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -1406,6 +1406,7 @@ dependencies = [
  "tokio",
  "tracing",
  "tracing-futures",
+ "tracing-test",
  "url",
 ]
 
@@ -1717,7 +1718,7 @@ checksum = "bdfb8ce053d86b91919aad980c220b1fb8401a9394410e1c289ed7e66b61835d"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -2076,7 +2077,7 @@ checksum = "d5dacb10c5b3bb92d46ba347505a9041e676bb20ad220101326bffb0c93031ee"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -2515,7 +2516,7 @@ dependencies = [
  "bytes",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -2620,7 +2621,7 @@ dependencies = [
  "proc-macro-crate",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -2781,7 +2782,7 @@ dependencies = [
  "proc-macro-hack",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -2825,7 +2826,7 @@ checksum = "710faf75e1b33345361201d36d04e98ac1ed8909151a017ed384700836104c74"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -2941,7 +2942,7 @@ dependencies = [
  "proc-macro-error-attr",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
  "version_check",
 ]
 
@@ -2964,9 +2965,9 @@ checksum = "dbf0c48bc1d91375ae5c3cd81e3722dff1abcf81a30960240640d223f59fe0e5"
 
 [[package]]
 name = "proc-macro2"
-version = "1.0.47"
+version = "1.0.92"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5ea3d908b0e36316caf9e9e2c4625cdde190a7e6f440d794667ed17a1855e725"
+checksum = "37d3544b3f2748c54e147655edb5025752e2303145b5aefb3c3ea2c78b973bb0"
 dependencies = [
  "unicode-ident",
 ]
@@ -2979,9 +2980,9 @@ checksum = "47c327e191621a2158159df97cdbc2e7074bb4e940275e35abf38eb3d2595754"
 
 [[package]]
 name = "quote"
-version = "1.0.16"
+version = "1.0.38"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b4af2ec4714533fcdf07e886f17025ace8b997b9ce51204ee69b6da831c3da57"
+checksum = "0e4dccaaaf89514f546c693ddc140f729f958c247918a13380cccc6078391acc"
 dependencies = [
  "proc-macro2",
 ]
@@ -3241,7 +3242,7 @@ checksum = "e33d7b2abe0c340d8797fe2907d3f20d3b5ea5908683618bfe80df7f621f672a"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -3438,7 +3439,7 @@ dependencies = [
  "proc-macro-crate",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -3585,7 +3586,7 @@ checksum = "94ed3a816fb1d101812f83e789f888322c34e291f894f19590dc310963e87a00"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -3634,7 +3635,7 @@ dependencies = [
  "proc-macro-error",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -3759,7 +3760,7 @@ checksum = "96e6310f022b5c02b3bba689166e833f6b96994a6ce1f138b653d2fd0519920f"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -3863,7 +3864,7 @@ dependencies = [
  "proc-macro2",
  "quote",
  "rustversion",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -3927,6 +3928,17 @@ dependencies = [
  "unicode-ident",
 ]
 
+[[package]]
+name = "syn"
+version = "2.0.93"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9c786062daee0d6db1132800e623df74274a0a87322d8e183338e01b3d98d058"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "unicode-ident",
+]
+
 [[package]]
 name = "synstructure"
 version = "0.12.6"
@@ -3935,7 +3947,7 @@ checksum = "f36bdaa60a83aca3921b5259d5400cbf5e90fc51931376a9bd4a0eb79aa7210f"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
  "unicode-xid",
 ]
 
@@ -4021,7 +4033,7 @@ checksum = "982d17546b47146b28f7c22e3d08465f6b8903d0ea13c1660d9d84a6e7adcdbb"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -4114,7 +4126,7 @@ checksum = "b557f72f448c511a979e2564e55d74e6c4432fc96ff4f6241bc6bded342643b7"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -4205,7 +4217,7 @@ checksum = "4017f8f45139870ca7e672686113917c71c7a6e02d4924eda67186083c03081a"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
 ]
 
 [[package]]
@@ -4257,6 +4269,27 @@ dependencies = [
  "tracing-log",
 ]
 
+[[package]]
+name = "tracing-test"
+version = "0.2.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "557b891436fe0d5e0e363427fc7f217abf9ccd510d5136549847bdcbcd011d68"
+dependencies = [
+ "tracing-core",
+ "tracing-subscriber",
+ "tracing-test-macro",
+]
+
+[[package]]
+name = "tracing-test-macro"
+version = "0.2.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "04659ddb06c87d233c566112c1c9c5b9e98256d9af50ec3bc9c8327f873a7568"
+dependencies = [
+ "quote",
+ "syn 2.0.93",
+]
+
 [[package]]
 name = "trezor-client"
 version = "0.0.7"
@@ -4479,7 +4512,7 @@ dependencies = [
  "once_cell",
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
  "wasm-bindgen-shared",
 ]
 
@@ -4513,7 +4546,7 @@ checksum = "07bc0c051dc5f23e307b13285f9d75df86bfdf816c5721e573dec1f9b8aa193c"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
  "wasm-bindgen-backend",
  "wasm-bindgen-shared",
 ]
@@ -4834,7 +4867,7 @@ checksum = "81e8f13fef10b63c06356d65d416b070798ddabcadc10d3ece0c5be9b3c7eddb"
 dependencies = [
  "proc-macro2",
  "quote",
- "syn",
+ "syn 1.0.103",
  "synstructure",
 ]
 
diff --git a/ethers-middleware/Cargo.toml b/ethers-middleware/Cargo.toml
index b53788bf8..41b57dd58 100644
--- a/ethers-middleware/Cargo.toml
+++ b/ethers-middleware/Cargo.toml
@@ -29,6 +29,7 @@ futures-util = { version = "^0.3" }
 futures-locks = { version = "0.7", default-features = false }
 tracing = { version = "0.1.37", default-features = false }
 tracing-futures = { version = "0.2.5", default-features = false }
+tracing-test = "0.2.2"
 
 # for gas oracles
 reqwest = { version = "0.11.13", default-features = false, features = ["json", "rustls-tls"] }
diff --git a/ethers-middleware/src/gas_escalator/mod.rs b/ethers-middleware/src/gas_escalator/mod.rs
index 7d3be4552..9ca6d3531 100644
--- a/ethers-middleware/src/gas_escalator/mod.rs
+++ b/ethers-middleware/src/gas_escalator/mod.rs
@@ -184,6 +184,7 @@ where
         &self.inner.inner
     }
 
+    #[instrument(skip(self, tx, block), name = "GasOracle::send_transaction")]
     async fn send_transaction<T: Into<TypedTransaction> + Send + Sync>(
         &self,
         tx: T,
@@ -206,7 +207,7 @@ where
 
         match self.inner.send_transaction(tx.clone(), block).await {
             Ok(pending_tx) => {
-                // insert the tx in the pending txs
+                tracing::debug!(tx = ?tx, tx_hash = ?pending_tx.tx_hash(), "Sent tx, adding to gas escalator watcher");
                 let mut lock = self.txs.lock().await;
                 lock.push(MonitoredTransaction {
                     hash: Some(*pending_tx),
@@ -217,7 +218,7 @@ where
                 Ok(pending_tx)
             }
             Err(err) => {
-                // insert the tx in the pending txs
+                tracing::warn!(tx = ?tx, "Failed to send tx, adding to gas escalator watcher regardless");
                 let mut lock = self.txs.lock().await;
                 lock.push(MonitoredTransaction {
                     hash: None,
@@ -269,6 +270,9 @@ pub struct EscalationTask<M, E> {
     txs: ToEscalate,
 }
 
+const RETRYABLE_ERRORS: [&str; 3] =
+    ["replacement transaction underpriced", "already known", "Fair pubdata price too high"];
+
 #[cfg(not(target_arch = "wasm32"))]
 impl<M, E: Clone> EscalationTask<M, E> {
     pub fn new(inner: M, escalator: E, frequency: Frequency, txs: ToEscalate) -> Self {
@@ -288,23 +292,13 @@ impl<M, E: Clone> EscalationTask<M, E> {
             // already landed onchain, meaning we no longer need to escalate it
             tracing::warn!(err = err_message, ?old_monitored_tx, ?new_tx, "Nonce error when escalating gas price. Tx may have already been included onchain. Dropping it from escalator");
             None
-        } else if err_message.contains("replacement transaction underpriced") {
-            // the gas escalation wasn't sufficient
-            tracing::warn!(
-                err = err_message,
-                old_tx = ?old_monitored_tx,
-                new_tx = ?new_tx,
-                "Escalated gas price was underpriced, re-adding to escalator"
-            );
-            // return the old tx_hash and creation time so the transaction is re-escalated
-            // as soon as `monitored_txs` are evaluated again
-            Some((old_monitored_tx.hash, old_monitored_tx.creation_time))
-        } else if err_message.contains("already known") {
+        } else if RETRYABLE_ERRORS.iter().any(|err_msg| err_message.contains(err_msg)) {
+            // if the error is one of the known retryable errors, we can keep trying to escalate
             tracing::warn!(
                 err = err_message,
-                old_tx = ?old_monitored_tx,
+                old_tx = ?old_monitored_tx.hash,
                 new_tx = ?new_tx,
-                "The escalator broadcasted the same transaction twice. Re-adding to attempt re-escalating"
+                "Encountered retryable error, re-adding to escalator"
             );
             // return the old tx_hash and creation time so the transaction is re-escalated
             // as soon as `monitored_txs` are evaluated again
@@ -312,7 +306,7 @@ impl<M, E: Clone> EscalationTask<M, E> {
         } else {
             tracing::error!(
                 err = err_message,
-                old_tx = ?old_monitored_tx,
+                old_tx = ?old_monitored_tx.hash,
                 new_tx = ?new_tx,
                 "Unexpected error when broadcasting gas-escalated transaction. Dropping it from escalator."
             );
@@ -378,9 +372,9 @@ impl<M, E: Clone> EscalationTask<M, E> {
                 None
             };
 
-            if receipt.is_some() {
+            if let Some(receipt) = receipt {
                 // tx was already included, can drop from escalator
-                tracing::debug!(tx = ?old_monitored_tx, "Transaction was included onchain, dropping from escalator");
+                tracing::debug!(tx = ?receipt.transaction_hash, "Transaction was included onchain, dropping from escalator");
                 continue;
             }
             let Some(new_tx) = old_monitored_tx.escalate_gas_price(self.escalator.clone()) else {
diff --git a/ethers-middleware/src/gas_oracle/middleware.rs b/ethers-middleware/src/gas_oracle/middleware.rs
index 272b01509..df5c42b0e 100644
--- a/ethers-middleware/src/gas_oracle/middleware.rs
+++ b/ethers-middleware/src/gas_oracle/middleware.rs
@@ -3,6 +3,7 @@ use async_trait::async_trait;
 use ethers_core::types::{transaction::eip2718::TypedTransaction, *};
 use ethers_providers::{FromErr, Middleware, PendingTransaction};
 use thiserror::Error;
+use tracing::instrument;
 
 #[derive(Debug)]
 /// Middleware used for fetching gas prices over an API instead of `eth_gasPrice`
@@ -56,6 +57,7 @@ where
         &self.inner
     }
 
+    #[instrument(skip(self), name = "GasOracle::fill_transaction")]
     async fn fill_transaction(
         &self,
         tx: &mut TypedTransaction,
@@ -85,6 +87,7 @@ where
                 }
             }
         };
+        tracing::debug!(?tx, "Filled transaction");
 
         self.inner().fill_transaction(tx, block).await.map_err(FromErr::from)
     }
@@ -100,12 +103,14 @@ where
         Ok(self.gas_oracle.estimate_eip1559_fees().await?)
     }
 
+    #[instrument(skip(self, tx, block), name = "GasOracle::send_transaction")]
     async fn send_transaction<T: Into<TypedTransaction> + Send + Sync>(
         &self,
         tx: T,
         block: Option<BlockId>,
     ) -> Result<PendingTransaction<'_, Self::Provider>, Self::Error> {
         let mut tx = tx.into();
+        tracing::debug!(?tx, "Sending transaction");
         self.fill_transaction(&mut tx, block).await?;
         self.inner.send_transaction(tx, block).await.map_err(MiddlewareError::MiddlewareError)
     }
diff --git a/ethers-middleware/src/nonce_manager.rs b/ethers-middleware/src/nonce_manager.rs
index b4a92c3dd..7905c7b78 100644
--- a/ethers-middleware/src/nonce_manager.rs
+++ b/ethers-middleware/src/nonce_manager.rs
@@ -3,6 +3,7 @@ use ethers_core::types::{transaction::eip2718::TypedTransaction, *};
 use ethers_providers::{FromErr, Middleware, PendingTransaction};
 use std::sync::atomic::{AtomicBool, AtomicU64, Ordering};
 use thiserror::Error;
+use tracing::instrument;
 
 #[derive(Debug)]
 /// Middleware used for calculating nonces locally, useful for signing multiple
@@ -106,6 +107,7 @@ where
         &self.inner
     }
 
+    #[instrument(skip(self), name = "NonceManager::fill_transaction")]
     async fn fill_transaction(
         &self,
         tx: &mut TypedTransaction,
@@ -125,6 +127,7 @@ where
     /// Signs and broadcasts the transaction. The optional parameter `block` can be passed so that
     /// gas cost and nonce calculations take it into account. For simple transactions this can be
     /// left to `None`.
+    #[instrument(skip(self, tx, block), name = "NonceManager::send_transaction")]
     async fn send_transaction<T: Into<TypedTransaction> + Send + Sync>(
         &self,
         tx: T,
@@ -135,21 +138,43 @@ where
         if tx.nonce().is_none() {
             tx.set_nonce(self.get_transaction_count_with_manager(block).await?);
         }
-
+        let nonce = tx.nonce();
+        tracing::debug!(?nonce, "Sending transaction");
         match self.inner.send_transaction(tx.clone(), block).await {
-            Ok(tx_hash) => Ok(tx_hash),
+            Ok(pending_tx) => {
+                tracing::debug!(?nonce, "Sent transaction");
+                Ok(pending_tx)
+            }
             Err(err) => {
-                let nonce = self.get_transaction_count(self.address, block).await?;
-                if nonce != self.nonce.load(Ordering::SeqCst).into() {
+                tracing::error!(
+                    ?nonce,
+                    error=?err,
+                    "Error sending transaction. Checking onchain nonce."
+                );
+                let onchain_nonce = self.get_transaction_count(self.address, block).await?;
+                let internal_nonce = self.nonce.load(Ordering::SeqCst);
+                if onchain_nonce != internal_nonce.into() {
                     // try re-submitting the transaction with the correct nonce if there
                     // was a nonce mismatch
-                    self.nonce.store(nonce.as_u64(), Ordering::SeqCst);
-                    tx.set_nonce(nonce);
+                    self.nonce.store(onchain_nonce.as_u64(), Ordering::SeqCst);
+                    tx.set_nonce(onchain_nonce);
+                    tracing::warn!(
+                        onchain_nonce=?onchain_nonce.as_u64(),
+                        ?internal_nonce,
+                        error=?err,
+                        "Onchain nonce didn't match internal nonce. Resending transaction with updated nonce."
+                    );
                     self.inner
                         .send_transaction(tx, block)
                         .await
                         .map_err(NonceManagerError::MiddlewareError)
                 } else {
+                    tracing::warn!(
+                        onchain_nonce=?onchain_nonce.as_u64(),
+                        ?internal_nonce,
+                        error=?err,
+                        "Onchain nonce matches internal nonce. Propagating error."
+                    );
                     // propagate the error otherwise
                     Err(NonceManagerError::MiddlewareError(err))
                 }
diff --git a/ethers-middleware/src/signer.rs b/ethers-middleware/src/signer.rs
index 36af4f031..924643ae2 100644
--- a/ethers-middleware/src/signer.rs
+++ b/ethers-middleware/src/signer.rs
@@ -5,6 +5,7 @@ use ethers_core::types::{
 use ethers_providers::{maybe, FromErr, Middleware, PendingTransaction};
 use ethers_signers::Signer;
 use std::convert::TryFrom;
+use tracing::instrument;
 
 use async_trait::async_trait;
 use thiserror::Error;
@@ -233,6 +234,7 @@ where
     }
 
     /// Helper for filling a transaction's nonce using the wallet
+    #[instrument(skip(self), name = "SignerMiddleware::fill_transaction")]
     async fn fill_transaction(
         &self,
         tx: &mut TypedTransaction,
@@ -276,12 +278,14 @@ where
     /// Signs and broadcasts the transaction. The optional parameter `block` can be passed so that
     /// gas cost and nonce calculations take it into account. For simple transactions this can be
     /// left to `None`.
+    #[instrument(skip(self, tx, block), name = "SignerMiddleware::send_transaction")]
     async fn send_transaction<T: Into<TypedTransaction> + Send + Sync>(
         &self,
         tx: T,
         block: Option<BlockId>,
     ) -> Result<PendingTransaction<'_, Self::Provider>, Self::Error> {
         let mut tx = tx.into();
+        tracing::debug!(nonce=?tx.nonce(), "Sending transaction");
 
         // fill any missing fields
         self.fill_transaction(&mut tx, block).await?;
@@ -292,7 +296,7 @@ where
                 .inner
                 .send_transaction(tx, block)
                 .await
-                .map_err(SignerMiddlewareError::MiddlewareError)
+                .map_err(SignerMiddlewareError::MiddlewareError);
         }
 
         // if we have a nonce manager set, we should try handling the result in
diff --git a/ethers-middleware/tests/gas_escalator.rs b/ethers-middleware/tests/gas_escalator.rs
index 3cbea38ee..0e5981c08 100644
--- a/ethers-middleware/tests/gas_escalator.rs
+++ b/ethers-middleware/tests/gas_escalator.rs
@@ -15,6 +15,7 @@ use instant::Duration;
 use tokio::time::sleep;
 
 #[tokio::test]
+#[tracing_test::traced_test]
 async fn gas_escalator_legacy_works() {
     // TODO: show tracing logs in the test
 
@@ -63,6 +64,7 @@ async fn gas_escalator_legacy_works() {
 }
 
 #[tokio::test]
+#[tracing_test::traced_test]
 async fn gas_escalator_1559_works() {
     // TODO: show tracing logs in the test