diff --git a/src/executor.rs b/src/executor.rs
index 3b9558b5..4280037c 100644
--- a/src/executor.rs
+++ b/src/executor.rs
@@ -37,7 +37,6 @@ impl RunType {
         }
     }
 
-    #[cfg(feature = "self-update")]
     /// Tells whether we're performing a dry run.
     pub fn dry(self) -> bool {
         match self {
diff --git a/src/main.rs b/src/main.rs
index fd5a2f53..42a2df80 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -136,7 +136,7 @@ fn run() -> Result<(), Error> {
             execute(
                 &mut report,
                 remote_topgrade,
-                || generic::run_remote_topgrade(run_type, remote_topgrade),
+                || generic::run_remote_topgrade(run_type, remote_topgrade, config.run_in_tmux()),
                 config.no_retry(),
             )?;
         }
diff --git a/src/steps/generic.rs b/src/steps/generic.rs
index ff0b0dfc..4d9a2bc2 100644
--- a/src/steps/generic.rs
+++ b/src/steps/generic.rs
@@ -137,17 +137,27 @@ pub fn run_composer_update(base_dirs: &BaseDirs, run_type: RunType) -> Result<()
     Ok(())
 }
 
-pub fn run_remote_topgrade(run_type: RunType, hostname: &str) -> Result<(), Error> {
+pub fn run_remote_topgrade(run_type: RunType, hostname: &str, run_in_tmux: bool) -> Result<(), Error> {
     let ssh = utils::require("ssh")?;
 
-    run_type
-        .execute(&ssh)
-        .args(&[
-            "-t",
-            hostname,
-            "env",
-            &format!("TOPGRADE_PREFIX={}", hostname),
-            "topgrade",
-        ])
-        .check_run()
+    if run_in_tmux && !run_type.dry() {
+        #[cfg(unix)]
+        {
+            crate::tmux::run_remote_topgrade(hostname, &ssh)?;
+            Err(ErrorKind::SkipStep)?
+        }
+
+        unreachable!("Tmux execution is only implemented in Unix");
+    } else {
+        run_type
+            .execute(&ssh)
+            .args(&[
+                "-t",
+                hostname,
+                "env",
+                &format!("TOPGRADE_PREFIX={}", hostname),
+                "topgrade",
+            ])
+            .check_run()
+    }
 }
diff --git a/src/steps/tmux.rs b/src/steps/tmux.rs
index cc7a0414..32e7056f 100644
--- a/src/steps/tmux.rs
+++ b/src/steps/tmux.rs
@@ -82,3 +82,19 @@ pub fn run_in_tmux() -> ! {
         exit(0);
     }
 }
+
+pub fn run_remote_topgrade(hostname: &str, ssh: &Path) -> Result<(), Error> {
+    let command = format!(
+        "{ssh} -t {hostname} env TOPGRADE_PREFIX={hostname} topgrade",
+        ssh = ssh.display(),
+        hostname = hostname
+    );
+    Command::new(which("tmux").unwrap())
+        .args(&["new-window", "-a", "-t", "topgrade:1", "-n", hostname, &command])
+        .env_remove("TMUX")
+        .spawn()
+        .context(ErrorKind::ProcessExecution)?
+        .wait()
+        .context(ErrorKind::ProcessExecution)?
+        .check()
+}