diff --git a/CHANGELOG.md b/CHANGELOG.md
index 77a2aa9..da45d05 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Added
 
 - "Encrypting with Sops" documentation example.
+- `--ssh-verbose` / `--sv` argument which increases verbosity of SSH commands.
 
 ### Changed
 
diff --git a/crates/cli/src/cli.rs b/crates/cli/src/cli.rs
index 5e558ee..235a838 100644
--- a/crates/cli/src/cli.rs
+++ b/crates/cli/src/cli.rs
@@ -2,7 +2,7 @@
 // Copyright 2024-2025 wire Contributors
 
 use clap::builder::PossibleValue;
-use clap::{Args, Parser, Subcommand, ValueEnum};
+use clap::{ArgAction, Args, Parser, Subcommand, ValueEnum};
 use clap::{ValueHint, crate_version};
 use clap_complete::CompletionCandidate;
 use clap_complete::engine::ArgValueCompleter;
@@ -213,6 +213,10 @@ pub struct ApplyArgs {
     /// Vulnerable to man-in-the-middle attacks, use with caution.
     #[arg(long, default_value_t = false)]
     pub ssh_accept_host: bool,
+
+    /// Increase debug verbosity of SSH commands.
+    #[arg(long, visible_alias = "sv", action = ArgAction::Count, default_value_t = 0, value_parser=less_than_3)]
+    pub ssh_verbose: u8,
 }
 
 #[derive(Clone, Debug)]
@@ -332,6 +336,10 @@ impl ToSubCommandModifiers for Cli {
                 }
                 _ => wire_core::StrictHostKeyChecking::default(),
             },
+            ssh_verbosity: match &self.command {
+                Commands::Apply(args) => args.ssh_verbose.into(),
+                _ => 0,
+            },
         }
     }
 }
@@ -381,6 +389,10 @@ fn node_names_completer(current: &std::ffi::OsStr) -> Vec<CompletionCandidate> {
     })
 }
 
+fn less_than_3(s: &str) -> Result<u8, String> {
+    number_range(s, 0, 3)
+}
+
 #[cfg(test)]
 mod tests {
     use std::assert_matches::assert_matches;
diff --git a/crates/core/src/commands/pty/output.rs b/crates/core/src/commands/pty/output.rs
index 74407da..3aa0d27 100644
--- a/crates/core/src/commands/pty/output.rs
+++ b/crates/core/src/commands/pty/output.rs
@@ -221,43 +221,59 @@ fn search_string(
     status_sender: &watch::Sender<Status>,
     began_tx: &mut Option<oneshot::Sender<()>>,
 ) -> SearchFindings {
-    let searched = aho_corasick
-        .find_iter(haystack)
-        .map(|x| x.pattern())
-        .collect::<Vec<_>>();
-
-    let started = if searched.contains(&STARTED_PATTERN) {
-        debug!("start needle was found, switching mode...");
-        if let Some(began_tx) = began_tx.take() {
-            let _ = began_tx.send(());
+    for haystack in haystack.split(|&b| b == b'\n') {
+        if haystack.starts_with(b"debug") || haystack.starts_with(b"ssh") {
+            tracing::log::log!(
+                if haystack.starts_with(b"ssh") {
+                    tracing::log::Level::Error
+                } else {
+                    tracing::log::Level::Debug
+                },
+                "{}",
+                String::from_utf8_lossy(haystack)
+            );
+
+            continue;
         }
-        true
-    } else {
-        false
-    };
-
-    let succeeded = if searched.contains(&SUCCEEDED_PATTERN) {
-        debug!("succeed needle was found, marking child as succeeding.");
-        status_sender.send_replace(Status::Done { success: true });
-        true
-    } else {
-        false
-    };
-
-    let failed = if searched.contains(&FAILED_PATTERN) {
-        debug!("failed needle was found, elevated child did not succeed.");
-        status_sender.send_replace(Status::Done { success: false });
-        true
-    } else {
-        false
-    };
 
-    if succeeded || failed {
-        return SearchFindings::Terminate;
-    }
+        let searched = aho_corasick
+            .find_iter(haystack)
+            .map(|x| x.pattern())
+            .collect::<Vec<_>>();
+
+        let started = if searched.contains(&STARTED_PATTERN) {
+            debug!("start needle was found, switching mode...");
+            if let Some(began_tx) = began_tx.take() {
+                let _ = began_tx.send(());
+            }
+            true
+        } else {
+            false
+        };
+
+        let succeeded = if searched.contains(&SUCCEEDED_PATTERN) {
+            debug!("succeed needle was found, marking child as succeeding.");
+            status_sender.send_replace(Status::Done { success: true });
+            true
+        } else {
+            false
+        };
+
+        let failed = if searched.contains(&FAILED_PATTERN) {
+            debug!("failed needle was found, elevated child did not succeed.");
+            status_sender.send_replace(Status::Done { success: false });
+            true
+        } else {
+            false
+        };
+
+        if succeeded || failed {
+            return SearchFindings::Terminate;
+        }
 
-    if started {
-        return SearchFindings::Started;
+        if started {
+            return SearchFindings::Started;
+        }
     }
 
     SearchFindings::None
diff --git a/crates/core/src/hive/node.rs b/crates/core/src/hive/node.rs
index c4d90fc..65e21fe 100644
--- a/crates/core/src/hive/node.rs
+++ b/crates/core/src/hive/node.rs
@@ -94,6 +94,10 @@ impl Target {
         vector.push("-o".to_string());
         vector.extend(options.into_iter().intersperse("-o".to_string()));
 
+        if modifiers.ssh_verbosity > 0 {
+            vector.push(format!("-{}", "v".repeat(modifiers.ssh_verbosity)));
+        }
+
         Ok(vector)
     }
 
diff --git a/crates/core/src/lib.rs b/crates/core/src/lib.rs
index a1b43a4..9aaf23c 100644
--- a/crates/core/src/lib.rs
+++ b/crates/core/src/lib.rs
@@ -44,6 +44,7 @@ pub struct SubCommandModifiers {
     pub show_trace: bool,
     pub non_interactive: bool,
     pub ssh_accept_host: StrictHostKeyChecking,
+    pub ssh_verbosity: usize,
 }
 
 impl Default for SubCommandModifiers {
@@ -52,6 +53,7 @@ impl Default for SubCommandModifiers {
             show_trace: false,
             non_interactive: !std::io::stdin().is_terminal(),
             ssh_accept_host: StrictHostKeyChecking::default(),
+            ssh_verbosity: 0,
         }
     }
 }