diff --git a/crates/repl/src/kernels/ssh_kernel.rs b/crates/repl/src/kernels/ssh_kernel.rs
index 53be6622379cfcbf3ceeb6db425eeede9b226860..797b111a14345267e01c60c6803787c8f1d0f6a2 100644
--- a/crates/repl/src/kernels/ssh_kernel.rs
+++ b/crates/repl/src/kernels/ssh_kernel.rs
@@ -215,7 +215,7 @@ impl SshRunningKernel {
                 &session_id,
             )
             .await
-            .context("failed to create iopub connection")?;
+            .context("Failed to create iopub connection. Is `ipykernel` installed in the remote environment? Try running `pip install ipykernel` on the remote host.")?;
 
             let peer_identity = runtimelib::peer_identity_for_session(&session_id)?;
             let shell_socket = runtimelib::create_client_shell_connection_with_identity(
diff --git a/crates/repl/src/kernels/wsl_kernel.rs b/crates/repl/src/kernels/wsl_kernel.rs
index d9ac05c5fc8c2cb756898ff449d6714b78cb7997..be76d7ddccb7f199a368b76a1f21bf65fe6f2902 100644
--- a/crates/repl/src/kernels/wsl_kernel.rs
+++ b/crates/repl/src/kernels/wsl_kernel.rs
@@ -354,7 +354,8 @@ impl WslRunningKernel {
                 "",
                 &session_id,
             )
-            .await?;
+            .await
+            .context("Failed to create iopub connection. Is `ipykernel` installed in the WSL environment? Try running `pip install ipykernel` inside your WSL distribution.")?;
 
             let peer_identity = runtimelib::peer_identity_for_session(&session_id)?;
             let shell_socket = runtimelib::create_client_shell_connection_with_identity(