diff --git a/gef.py b/gef.py
index 41cb61da6..4799c5e69 100644
--- a/gef.py
+++ b/gef.py
@@ -3530,7 +3530,7 @@ def is_target_remote_or_extended(conn: gdb.TargetConnection | None = None) -> bo
     return is_target_remote(conn) or is_target_extended_remote(conn)
 
 
-def is_running_under_qemu() -> bool:
+def is_running_in_qemu() -> bool:
     "See https://www.qemu.org/docs/master/system/gdb.html "
     if not is_target_remote():
         return False
@@ -3538,15 +3538,15 @@ def is_running_under_qemu() -> bool:
     return "ENABLE=" in response
 
 
-def is_running_under_qemu_user() -> bool:
-    if not is_running_under_qemu():
+def is_running_in_qemu_user() -> bool:
+    if not is_running_in_qemu():
         return False
     response = gdb.execute("maintenance packet qOffsets", to_string=True, from_tty=False) or "" # Use `qAttached`?
     return "Text=" in response
 
 
-def is_running_under_qemu_system() -> bool:
-    if not is_running_under_qemu():
+def is_running_in_qemu_system() -> bool:
+    if not is_running_in_qemu():
         return False
     # Use "maintenance packet qqemu.PhyMemMode"?
     response = gdb.execute("maintenance packet qOffsets", to_string=True, from_tty=False) or ""
@@ -3554,9 +3554,7 @@ def is_running_under_qemu_system() -> bool:
 
 
 def is_running_in_gdbserver() -> bool:
-    if is_running_under_qemu():
-        return False
-    return not is_running_under_qemu()
+    return not is_running_in_qemu()
 
 
 def is_running_in_rr() -> bool:
@@ -7447,7 +7445,7 @@ def __init__(self) -> None:
     def do_invoke(self, _: list[str], **kwargs: Any) -> None:
         args : argparse.Namespace = kwargs["arguments"]
 
-        if is_running_under_qemu_system():
+        if is_running_in_qemu_system():
             err("Unsupported")
             return
 
@@ -11345,7 +11343,7 @@ def __repr__(self) -> str:
     def auxiliary_vector(self) -> dict[str, int] | None:
         if not is_alive():
             return None
-        if is_running_under_qemu_system():
+        if is_running_in_qemu_system():
             return None
         if not self._auxiliary_vector:
             auxiliary_vector = {}
@@ -11493,9 +11491,9 @@ def prompt_string(self) -> str:
 
         @staticmethod
         def init() -> "GefRemoteSessionManager.RemoteMode":
-            if is_running_under_qemu_system():
+            if is_running_in_qemu_system():
                 return GefRemoteSessionManager.RemoteMode.QEMU_SYSTEM
-            if is_running_under_qemu_user():
+            if is_running_in_qemu_user():
                 return GefRemoteSessionManager.RemoteMode.QEMU_USER
             if is_running_in_rr():
                 return GefRemoteSessionManager.RemoteMode.RR
@@ -11619,7 +11617,7 @@ def connect(self, pid: int) -> bool:
 
     def setup(self) -> bool:
         # setup remote adequately depending on remote or qemu mode
-        dbg(f"Setting up the {self._mode} session")
+        info(f"Setting up remote session as '{self._mode}'")
         match self.mode:
             case GefRemoteSessionManager.RemoteMode.QEMU_USER:
                 self.__setup_qemu_user()
@@ -11826,21 +11824,24 @@ def reset_caches(self) -> None:
         return
 
 
+def target_remote_hook():
+    # disable the context until the session has been fully established
+    gef.config["context.enable"] = False
+
+
 def target_remote_posthook():
-    print(f"{is_target_remote()=}")
-    print(f"{is_target_remote_or_extended()=}")
-    print(f"{is_target_extended_remote()=}")
-    print(f"{is_running_under_qemu()=}")
-    print(f"{is_running_under_qemu_system()=}")
-    print(f"{is_running_under_qemu_user()=}")
-    print(f"{is_running_in_gdbserver()=}")
-    print(f"{is_running_in_rr()=}")
     conn = gdb.selected_inferior().connection
     if not isinstance(conn, gdb.RemoteTargetConnection):
         raise TypeError("Expected type gdb.RemoteTargetConnection")
     assert is_target_remote_or_extended(conn), "Target is not remote"
     gef.session.remote = GefRemoteSessionManager(conn)
 
+    # re-enable context
+    gef.config["context.enable"] = True
+
+    # if here, no exception was thrown, print context
+    gdb.execute("context")
+
 
 if __name__ == "__main__":
     if sys.version_info[0] == 2:
@@ -11903,14 +11904,18 @@ def target_remote_posthook():
 
     GefTmuxSetup()
 
-    # Initialize `target *remote` post hooks
+    # Initialize `target *remote` pre/post hooks
     hook = """
-    define target hookpost-{0}
-        pi target_remote_posthook()
+    define target hook{1}-{0}
+        pi target_remote_{1}hook()
     end
     """
-    gdb.execute(hook.format("remote"))
-    gdb.execute(hook.format("extended-remote"))
+    # pre-hooks
+    gdb.execute(hook.format("remote", ""))
+    gdb.execute(hook.format("extended-remote", ""))
+    # post-hooks
+    gdb.execute(hook.format("remote", "post"))
+    gdb.execute(hook.format("extended-remote", "post"))
 
     # restore saved breakpoints (if any)
     bkp_fpath = pathlib.Path(gef.config["gef.autosave_breakpoints_file"]).expanduser().absolute()
diff --git a/tests/api/gef_remote.py b/tests/api/gef_remote.py
new file mode 100644
index 000000000..fceb96546
--- /dev/null
+++ b/tests/api/gef_remote.py
@@ -0,0 +1,87 @@
+"""
+`target remote/extended-remote` test module.
+"""
+
+
+from tests.base import RemoteGefUnitTestGeneric
+from tests.utils import debug_target, gdbserver_session, gdbserver_multi_session, get_random_port, qemuuser_session
+
+
+class GefRemoteApi(RemoteGefUnitTestGeneric):
+
+    def setUp(self) -> None:
+        self._target = debug_target("default")
+        return super().setUp()
+
+    def test_gef_remote_test_gdbserver(self):
+        """Test `gdbserver file`"""
+        _gdb = self._gdb
+        _root = self._conn.root
+        port = get_random_port()
+
+        with gdbserver_session(port=port):
+            assert not _root.eval("is_target_remote()")
+            assert not _root.eval("is_target_remote_or_extended()")
+            assert not _root.eval("is_running_in_gdbserver()")
+
+            _gdb.execute(f"target remote :{port}")
+
+            assert _root.eval("is_target_remote()")
+            assert _root.eval("is_target_remote_or_extended()")
+            assert _root.eval("is_running_in_gdbserver()")
+
+            assert not _root.eval("is_target_extended_remote()")
+            assert not _root.eval("is_running_under_qemu()")
+            assert not _root.eval("is_running_under_qemu_system()")
+            assert not _root.eval("is_running_under_qemu_user()")
+            assert not _root.eval("is_running_in_rr()")
+
+    def test_gef_remote_test_gdbserver_multi(self):
+        """Test `gdbserver --multi file`"""
+        _gdb = self._gdb
+        _root = self._conn.root
+        port = get_random_port()
+
+        with gdbserver_multi_session(port=port):
+            assert not _root.eval("is_target_remote()")
+            assert not _root.eval("is_target_remote_or_extended()")
+            assert not _root.eval("is_running_in_gdbserver()")
+
+            _gdb.execute(f"target extended-remote :{port}")
+
+            assert _root.eval("is_target_remote()")
+            assert _root.eval("is_target_remote_or_extended()")
+            assert _root.eval("is_target_extended_remote()")
+            assert _root.eval("is_running_in_gdbserver()")
+
+            assert not _root.eval("is_running_under_qemu()")
+            assert not _root.eval("is_running_under_qemu_system()")
+            assert not _root.eval("is_running_under_qemu_user()")
+            assert not _root.eval("is_running_in_rr()")
+
+    def test_gef_remote_test_qemuuser(self):
+        """Test `qemu-user -g`"""
+        _gdb = self._gdb
+        _root = self._conn.root
+        port = get_random_port()
+
+        with qemuuser_session(port=port):
+            assert not _root.eval("is_target_remote()")
+            assert not _root.eval("is_target_remote_or_extended()")
+            assert not _root.eval("is_running_in_gdbserver()")
+
+            _gdb.execute(f"target remote :{port}")
+
+            assert _root.eval("is_target_remote()")
+            assert _root.eval("is_target_remote_or_extended()")
+            assert _root.eval("is_running_under_qemu()")
+            assert _root.eval("is_running_under_qemu_user()")
+
+            assert not _root.eval("is_target_extended_remote()")
+            assert not _root.eval("is_running_under_qemu_system()")
+            assert not _root.eval("is_running_in_gdbserver()")
+            assert not _root.eval("is_running_in_rr()")
+
+    # TODO add tests for
+    #  - [ ] qemu-system
+    #  - [ ] rr
diff --git a/tests/base.py b/tests/base.py
index 868923d3a..e1584eaf7 100644
--- a/tests/base.py
+++ b/tests/base.py
@@ -10,7 +10,7 @@
 
 import rpyc
 
-from .utils import debug_target
+from .utils import debug_target, get_random_port
 
 COVERAGE_DIR = os.getenv("COVERAGE_DIR", "")
 GEF_PATH = pathlib.Path(os.getenv("GEF_PATH", "gef.py")).absolute()
@@ -58,7 +58,7 @@ def __setup(self):
         #
         # Select a random tcp port for rpyc
         #
-        self._port = random.randint(1025, 65535)
+        self._port = get_random_port()
         self._commands = ""
 
         if COVERAGE_DIR:
diff --git a/tests/utils.py b/tests/utils.py
index f88d3b304..8b9247758 100644
--- a/tests/utils.py
+++ b/tests/utils.py
@@ -12,6 +12,7 @@
 import subprocess
 import tempfile
 import time
+import random
 
 from typing import Iterable, List, Optional, Union
 from urllib.request import urlopen
@@ -112,6 +113,13 @@ def start_gdbserver(
     logging.debug(f"Starting {cmd}")
     return subprocess.Popen(cmd)
 
+def start_gdbserver_multi(
+    host: str = GDBSERVER_DEFAULT_HOST,
+    port: int = GDBSERVER_DEFAULT_PORT,
+) -> subprocess.Popen:
+    cmd = [GDBSERVER_BINARY, "--multi", f"{host}:{port}"]
+    logging.debug(f"Starting {cmd}")
+    return subprocess.Popen(cmd)
 
 def stop_gdbserver(gdbserver: subprocess.Popen) -> None:
     """Stop the gdbserver and wait until it is terminated if it was
@@ -138,6 +146,17 @@ def gdbserver_session(
     finally:
         stop_gdbserver(sess)
 
+@contextlib.contextmanager
+def gdbserver_multi_session(
+    port: int = GDBSERVER_DEFAULT_PORT,
+    host: str = GDBSERVER_DEFAULT_HOST,
+):
+    sess = start_gdbserver_multi(host, port)
+    try:
+        time.sleep(1)  # forced delay to allow gdbserver to start listening
+        yield sess
+    finally:
+        stop_gdbserver(sess)
 
 def start_qemuuser(
     exe: Union[str, pathlib.Path] = debug_target("default"),
@@ -301,3 +320,14 @@ def p32(x: int) -> bytes:
 
 def p64(x: int) -> bytes:
     return struct.pack("<Q", x)
+
+
+__available_ports = list()
+def get_random_port() -> int:
+    global __available_ports
+    if len(__available_ports) < 2:
+        __available_ports = list( range(1024, 65535) )
+    idx = random.choice(range(len(__available_ports)))
+    port = __available_ports[idx]
+    __available_ports.pop(idx)
+    return port