diff --git a/src/server/client.rs b/src/server/client.rs
index ff6fa7f675c..5e68d3cbf97 100644
--- a/src/server/client.rs
+++ b/src/server/client.rs
@@ -128,8 +128,12 @@ fn client_thread(
                         next_serial += 1;
                         promises.insert(serial, promise);
 
-                        pdu.encode(reconnectable.stream(), serial)?;
-                        reconnectable.stream().flush()?;
+                        pdu.encode(reconnectable.stream(), serial)
+                            .context("encoding a PDU to send to the server")?;
+                        reconnectable
+                            .stream()
+                            .flush()
+                            .context("flushing PDU to server")?;
                     }
                 },
                 Err(TryRecvError::Empty) => break,
@@ -166,7 +170,8 @@ fn client_thread(
                     Ok(Some(decoded)) => {
                         log::trace!("decoded serial {}", decoded.serial);
                         if decoded.serial == 0 {
-                            process_unilateral(local_domain_id, decoded)?;
+                            process_unilateral(local_domain_id, decoded)
+                                .context("processing unilateral PDU from server")?;
                         } else if let Some(mut promise) = promises.remove(&decoded.serial) {
                             promise.result(Ok(decoded.pdu));
                         } else {
@@ -582,7 +587,7 @@ impl Reconnectable {
             .configure()?
             .verify_hostname(!tls_client.accept_invalid_hostnames);
 
-        ui.output_str(&format!("Connecting to {}\n", remote_address));
+        ui.output_str(&format!("Connecting to {} using TLS\n", remote_address));
         let stream = TcpStream::connect(remote_address)
             .with_context(|| format!("connecting to {}", remote_address))?;
         stream.set_nodelay(true)?;
@@ -606,7 +611,7 @@ impl Reconnectable {
                     )
                 })?,
         );
-        ui.output_str("Connected!\n");
+        ui.output_str("TLS Connected!\n");
         self.stream.replace(stream);
         Ok(())
     }
diff --git a/src/server/domain.rs b/src/server/domain.rs
index 0df953bd15f..db1d326c1cf 100644
--- a/src/server/domain.rs
+++ b/src/server/domain.rs
@@ -302,9 +302,14 @@ impl Domain for ClientDomain {
             }
         };
 
+        ui.output_str("Version check OK!  Requesting tab list...\n");
         let tabs = client.list_tabs().await?;
-
+        ui.output_str(&format!(
+            "Server has {} tabs.  Attaching to local UI...\n",
+            tabs.tabs.len()
+        ));
         ClientDomain::finish_attach(domain_id, client, tabs)?;
+        ui.output_str("Attached!\n");
         drop(activity);
         ui.close();
         Ok(())
diff --git a/src/ssh.rs b/src/ssh.rs
index c60e22a2708..29c55bcfbd2 100644
--- a/src/ssh.rs
+++ b/src/ssh.rs
@@ -63,11 +63,11 @@ pub fn ssh_connect_with_ui(
         }
     };
 
-    ui.output_str(&format!("Connecting to {}\n", remote_address));
+    ui.output_str(&format!("Connecting to {} using SSH\n", remote_address));
 
     let tcp = TcpStream::connect(&remote_address)
         .with_context(|| format!("ssh connecting to {}", remote_address))?;
-    ui.output_str("Connected OK!\n");
+    ui.output_str("SSH: Connected OK!\n");
     tcp.set_nodelay(true)?;
     sess.set_tcp_stream(tcp);
     sess.handshake()
@@ -185,7 +185,7 @@ pub fn ssh_connect_with_ui(
                 "Password authentication for {}@{}\n",
                 username, remote_address
             ));
-            let pass = ui.password("Password: ")?;
+            let pass = ui.password("🔐 Password: ")?;
             if let Err(err) = sess.userauth_password(username, &pass) {
                 log::error!("while attempting password auth: {}", err);
             }