diff --git a/lib/kamal/commands/app/execution.rb b/lib/kamal/commands/app/execution.rb
index 4434c26aa..1e4b42e5a 100644
--- a/lib/kamal/commands/app/execution.rb
+++ b/lib/kamal/commands/app/execution.rb
@@ -20,8 +20,8 @@ def execute_in_new_container(*command, interactive: false, env:)
       *command
   end
 
-  def execute_in_existing_container_over_ssh(*command,  env:)
-    run_over_ssh execute_in_existing_container(*command, interactive: true, env: env), host: host
+  def execute_in_existing_container_over_ssh(*command, env:)
+    run_over_ssh execute_in_existing_container(*command, interactive: true, env: env), host: host, interactive: true
   end
 
   def execute_in_new_container_over_ssh(*command, env:)
diff --git a/lib/kamal/commands/base.rb b/lib/kamal/commands/base.rb
index 7521780ad..c18efb22c 100644
--- a/lib/kamal/commands/base.rb
+++ b/lib/kamal/commands/base.rb
@@ -10,14 +10,16 @@ def initialize(config)
       @config = config
     end
 
-    def run_over_ssh(*command, host:)
+    def run_over_ssh(*command, host:, interactive: false)
       "ssh".tap do |cmd|
         if config.ssh.proxy && config.ssh.proxy.is_a?(Net::SSH::Proxy::Jump)
           cmd << " -J #{config.ssh.proxy.jump_proxies}"
         elsif config.ssh.proxy && config.ssh.proxy.is_a?(Net::SSH::Proxy::Command)
           cmd << " -o ProxyCommand='#{config.ssh.proxy.command_line_template}'"
         end
-        cmd << " -t #{config.ssh.user}@#{host} -p #{config.ssh.port} '#{command.join(" ").gsub("'", "'\\\\''")}'"
+        cmd << " -tt" if interactive # Add -tt for interactive sessions
+        cmd << " #{config.ssh.user}@#{host} -p #{config.ssh.port}"
+        cmd << " '#{command.join(" ").gsub("'", "'\\\\''")}'" unless interactive
       end
     end