diff --git a/pwncat/commands/escalate.py b/pwncat/commands/escalate.py
new file mode 100644
index 0000000..1d342fc
--- /dev/null
+++ b/pwncat/commands/escalate.py
@@ -0,0 +1,121 @@
+#!/usr/bin/env python3
+
+from pwncat.util import console
+from pwncat.modules import ModuleFailed
+from pwncat.commands.base import Complete, Parameter, CommandDefinition
+
+
+def get_user_choices(command: CommandDefinition):
+    if command.manager.target is None:
+        return
+
+    yield from (
+        user.name
+        for user in command.manager.target.run(
+            "enumerate", progress=False, types=["user"]
+        )
+    )
+
+
+class Command(CommandDefinition):
+    """
+    Attempt privilege escalation in the current session. This command
+    may initiate new sessions along the way to attain the privileges of
+    the requested user.
+
+    The list command is simply a wrapper around enumerating "escalation.*".
+    This makes the escalation workflow more straightforward, but is not
+    required."""
+
+    PROG = "escalate"
+    ARGS = {
+        "command": Parameter(
+            Complete.CHOICES, metavar="COMMAND", choices=["list", "run"]
+        ),
+        "--user,-u": Parameter(
+            Complete.CHOICES, metavar="USERNAME", choices=get_user_choices
+        ),
+    }
+
+    def run(self, manager: "pwncat.manager.Manager", args):
+
+        if args.command == "help":
+            self.parser.print_usage()
+            return
+
+        if args.user:
+            args.user = manager.target.find_user(name=args.user)
+        else:
+            # NOTE: this should find admin regardless of platform
+            args.user = manager.target.find_user(name="root")
+
+        if args.command == "list":
+            self.list_abilities(manager, args)
+        elif args.command == "run":
+            with manager.target.task(
+                f"escalating to [cyan]{args.user.name}[/cyan]"
+            ) as task:
+                self.do_escalate(manager, task, args.user)
+
+    def list_abilities(self, manager, args):
+        """This is just a wrapper for `run enumerate types=escalate.*`, but
+        it makes the workflow for escalation more apparent."""
+
+        found = False
+
+        for escalation in manager.target.run("enumerate", types=["escalate.*"]):
+            if args.user and args.user.id != escalation.uid:
+                continue
+            console.print(f"- {escalation.title(manager.target)}")
+            found = True
+
+        if not found and args.user:
+            console.log(
+                f"[yellow]warning[/yellow]: no escalations for {args.user.name}"
+            )
+        elif not found:
+            console.log("[yellow]warning[/yellow]: no escalations found")
+
+    def do_escalate(self, manager: "pwncat.manager.Manager", task, user, attempted=[]):
+        """ Execute escalations until we find one that works """
+
+        # Find escalations for users that weren't attempted already
+        escalations = [
+            e
+            for e in list(manager.target.run("enumerate", types=["escalate.*"]))
+            if e.uid not in attempted
+        ]
+
+        # Attempt escalation directly to the target user if possible
+        for escalation in (e for e in escalations if e.uid == user.id):
+            try:
+                manager.target.update_task(
+                    task, status=f"attempting {escalation.title(manager.target)}"
+                )
+                result = escalation.escalate(manager.target)
+                manager.target.layers.append(result)
+
+                manager.target.log(
+                    f"escalation to {user.name} [green]successful[/green]!"
+                )
+                return result
+            except ModuleFailed:
+                pass
+
+        # Attempt escalation to a different user and recurse
+        for escalation in (e for e in escalation if e.uid != user.id):
+            try:
+                manager.target.update_task(
+                    task, status=f"attempting {escalation.title(manager.target)}"
+                )
+                result = escalation.escalate(manager.target)
+                manager.target.layers.append(result)
+
+                try:
+                    self.do_escalate(manager, task, user, attempted + [escalation.uid])
+                except ModuleFailed:
+                    manager.target.layers.pop()(manager.target)
+            except ModuleFailed:
+                pass
+
+        manager.target.log("[yellow]warning[/yellow]: no working escalations found")
diff --git a/pwncat/commands/leave.py b/pwncat/commands/leave.py
new file mode 100644
index 0000000..f675b29
--- /dev/null
+++ b/pwncat/commands/leave.py
@@ -0,0 +1,37 @@
+#!/usr/bin/env python3
+
+from pwncat.commands.base import Complete, Parameter, CommandDefinition
+
+
+class Command(CommandDefinition):
+    """
+    Leave a layer of execution from this session. Layers are normally added
+    as sub-shells from escalation modules.
+    """
+
+    PROG = "leave"
+    ARGS = {
+        "count": Parameter(
+            Complete.NONE,
+            type=int,
+            default=1,
+            nargs="?",
+            help="number of layers to remove (default: 1)",
+        ),
+        "--all,-a": Parameter(
+            Complete.NONE,
+            action="store_true",
+            help="leave all active layers",
+        ),
+    }
+
+    def run(self, manager: "pwncat.manager.Manager", args):
+
+        try:
+            if args.all:
+                args.count = len(manager.target.layers)
+
+            for i in range(args.count):
+                manager.target.layers.pop()(manager.target)
+        except IndexError:
+            manager.target.log("[yellow]warning[/yellow]: no more layers to leave")
diff --git a/pwncat/facts/ability.py b/pwncat/facts/ability.py
index af2827a..d8ba094 100644
--- a/pwncat/facts/ability.py
+++ b/pwncat/facts/ability.py
@@ -7,11 +7,9 @@ from io import TextIOWrapper
 import pwncat.subprocess
 from pwncat.gtfobins import Stream, Capability
 from pwncat.platform.linux import LinuxReader, LinuxWriter
-from pwncat.modules.agnostic.enumerate.ability import (
-    ExecuteAbility,
-    FileReadAbility,
-    FileWriteAbility,
-)
+from pwncat.modules.agnostic.enumerate.ability import (ExecuteAbility,
+                                                       FileReadAbility,
+                                                       FileWriteAbility)
 
 
 class GTFOFileRead(FileReadAbility):
@@ -74,8 +72,9 @@ class GTFOFileRead(FileReadAbility):
 
         return raw_reader
 
-    def __str__(self):
-        return f"file read as UID:{self.uid} via {self.method.binary_path}"
+    def title(self, session):
+        user = session.find_user(uid=self.uid)
+        return f"file read as [blue]{user.name}[/blue] via [cyan]{self.method.binary_path}[/cyan]"
 
 
 class GTFOFileWrite(FileWriteAbility):
@@ -138,8 +137,9 @@ class GTFOFileWrite(FileWriteAbility):
 
         return raw_writer
 
-    def __str__(self):
-        return f"file write as UID:{self.uid} via {self.method.binary_path}"
+    def title(self, session):
+        user = session.find_user(uid=self.uid)
+        return f"file write as [blue]{user.name}[/blue] via [cyan]{self.method.binary_path}[/cyan]"
 
 
 class GTFOExecute(ExecuteAbility):
@@ -201,5 +201,6 @@ class GTFOExecute(ExecuteAbility):
 
         self.send_command(session, shell.encode("utf-8") + b"\n")
 
-    def __str__(self):
-        return f"execution as UID:{self.uid} via {self.method.binary_path}"
+    def title(self, session):
+        user = session.find_user(uid=self.uid)
+        return f"shell as [blue]{user.name}[/blue] via [cyan]{self.method.binary_path}[/cyan]"
diff --git a/pwncat/manager.py b/pwncat/manager.py
index 08664b9..6c77988 100644
--- a/pwncat/manager.py
+++ b/pwncat/manager.py
@@ -49,16 +49,9 @@ class Session:
         self.db = manager.db.open()
         self.module_depth = 0
         self.showing_progress = True
+        self.layers = []
 
-        self._progress = rich.progress.Progress(
-            "{task.fields[platform]}",
-            "•",
-            "{task.description}",
-            "•",
-            "{task.fields[status]}",
-            transient=True,
-            console=console,
-        )
+        self._progress = None
 
         # If necessary, build a new platform object
         if isinstance(platform, Platform):
@@ -207,7 +200,7 @@ class Session:
         # Ensure the variable exists even if an exception happens
         # prior to task creation
         task = None
-        started = self._progress._started
+        started = self._progress is not None  # ._started
 
         if "status" not in kwargs:
             kwargs["status"] = "..."
@@ -217,7 +210,16 @@ class Session:
         try:
             # Ensure this bar is started if we are the selected
             # target.
-            if self.manager.target == self:
+            if self.manager.target == self and not started:
+                self._progress = rich.progress.Progress(
+                    "{task.fields[platform]}",
+                    "•",
+                    "{task.description}",
+                    "•",
+                    "{task.fields[status]}",
+                    transient=True,
+                    console=console,
+                )
                 self._progress.start()
 
             # Create the new task
@@ -232,6 +234,7 @@ class Session:
             # nested tasks.
             if not started:
                 self._progress.stop()
+                self._progress = None
 
     def update_task(self, task, *args, **kwargs):
         """Update an active task"""
@@ -251,6 +254,10 @@ class Session:
     def close(self):
         """Close the session and remove from manager tracking"""
 
+        # Unwrap all layers in the session
+        while self.layers:
+            self.layers.pop()(self)
+
         self.platform.channel.close()
 
         self.died()
@@ -276,8 +283,6 @@ class Manager:
         self.config = Config()
         self.sessions: List[Session] = []
         self.modules: Dict[str, pwncat.modules.BaseModule] = {}
-        # self.engine = None
-        # self.SessionBuilder = None
         self._target = None
         self.parser = CommandParser(self)
         self.interactive_running = False
@@ -414,7 +419,7 @@ class Manager:
     def log(self, *args, **kwargs):
         """Output a log entry"""
 
-        if self.target is not None:
+        if self.target is not None and self.target._progress is not None:
             self.target._progress.log(*args, **kwargs)
         else:
             console.log(*args, **kwargs)
diff --git a/pwncat/modules/linux/enumerate/escalate/append_passwd.py b/pwncat/modules/linux/enumerate/escalate/append_passwd.py
index 4e64065..ef111eb 100644
--- a/pwncat/modules/linux/enumerate/escalate/append_passwd.py
+++ b/pwncat/modules/linux/enumerate/escalate/append_passwd.py
@@ -53,11 +53,12 @@ class AppendPasswd(EscalationReplace):
 
         try:
             session.platform.su(backdoor_user, password=backdoor_pass)
+            return lambda session: session.platform.channel.send(b"exit\n")
         except PermissionError:
             raise ModuleFailed("added user, but switch user failed")
 
-    def __str__(self):
-        return f"""add user via [blue]file write[/blue] as [red]root[/red] (w/ {self.ability})"""
+    def title(self, session: "pwncat.manager.Session"):
+        return f"""add user via [blue]file write[/blue] as [red]root[/red] (w/ {self.ability.title(session)})"""
 
 
 class Module(EnumerateModule):