diff --git a/src/imap.rs b/src/imap.rs
index 1533299932..29acf6e8c5 100644
--- a/src/imap.rs
+++ b/src/imap.rs
@@ -350,7 +350,7 @@ impl Imap {
 
         let login_params = prioritize_server_login_params(&context.sql, &self.lp, "imap").await?;
         let mut first_error = None;
-        for lp in login_params {
+        'candidate: for lp in login_params {
             info!(context, "IMAP trying to connect to {}.", lp.connection);
             let connection_candidate = lp.connection.clone();
             let client = match Client::connect(
@@ -366,7 +366,7 @@ impl Imap {
                 Err(err) => {
                     warn!(context, "{err:#}.");
                     first_error.get_or_insert(err);
-                    continue;
+                    continue 'candidate;
                 }
             };
 
@@ -395,18 +395,30 @@ impl Imap {
 
             match login_res {
                 Ok(mut session) => {
-                    let capabilities = determine_capabilities(&mut session).await?;
+                    let capabilities = match determine_capabilities(&mut session).await {
+                        Ok(capabilities) => capabilities,
+                        Err(err) => {
+                            warn!(context, "Failed to determine capabilities: {err:#}.");
+                            continue 'candidate;
+                        }
+                    };
                     let resync_request_sender = self.resync_request_sender.clone();
 
                     let session = if capabilities.can_compress {
                         info!(context, "Enabling IMAP compression.");
-                        let compressed_session = session
+                        let compressed_session = match session
                             .compress(|s| {
                                 let session_stream: Box<dyn SessionStream> = Box::new(s);
                                 session_stream
                             })
                             .await
-                            .context("Failed to enable IMAP compression")?;
+                        {
+                            Ok(compressed_session) => compressed_session,
+                            Err(err) => {
+                                warn!(context, "Failed to enable IMAP compression: {err:#}.");
+                                continue 'candidate;
+                            }
+                        };
                         Session::new(
                             compressed_session,
                             capabilities,