diff --git a/dissect/target/helpers/config.py b/dissect/target/helpers/config.py
index 8909012d1..7a1cc3faa 100644
--- a/dissect/target/helpers/config.py
+++ b/dissect/target/helpers/config.py
@@ -1,27 +1,35 @@
+from __future__ import annotations
+
 import ast
 import importlib.machinery
 import importlib.util
 import logging
 from pathlib import Path
 from types import ModuleType
-from typing import Optional, Union
 
 log = logging.getLogger(__name__)
 
 CONFIG_NAME = ".targetcfg.py"
 
 
-def load(path: Optional[Union[Path, str]]) -> ModuleType:
+def load(paths: list[Path | str] | Path | str | None) -> ModuleType:
+    """Attempt to load one configuration from the provided path(s)."""
+
+    if isinstance(paths, Path) or isinstance(paths, str):
+        paths = [paths]
+
     config_spec = importlib.machinery.ModuleSpec("config", None)
     config = importlib.util.module_from_spec(config_spec)
-    config_file = _find_config_file(path)
+    config_file = _find_config_file(paths)
+
     if config_file:
         config_values = _parse_ast(config_file.read_bytes())
         config.__dict__.update(config_values)
+
     return config
 
 
-def _parse_ast(code: str) -> dict[str, Union[str, int]]:
+def _parse_ast(code: str) -> dict[str, str | int]:
     # Only allow basic value assignments for backwards compatibility
     obj = {}
 
@@ -49,15 +57,19 @@ def _parse_ast(code: str) -> dict[str, Union[str, int]]:
     return obj
 
 
-def _find_config_file(path: Optional[Union[Path, str]]) -> Optional[Path]:
-    """Find a config file anywhere in the given path and return it.
+def _find_config_file(paths: list[Path | str] | None) -> Path | None:
+    """Find a config file anywhere in the given path(s) and return it.
 
     This algorithm allows parts of the path to not exist or the last part to be a filename.
     It also does not look in the root directory ('/') for config files.
     """
 
+    if not paths:
+        return
+
     config_file = None
-    if path:
+
+    for path in paths:
         path = Path(path)
         cur_path = path.absolute()
 
@@ -69,4 +81,7 @@ def _find_config_file(path: Optional[Union[Path, str]]) -> Optional[Path]:
                 config_file = cur_config
             cur_path = cur_path.parent
 
+        if config_file:
+            break
+
     return config_file
diff --git a/dissect/target/target.py b/dissect/target/target.py
index ca198baca..1b732a322 100644
--- a/dissect/target/target.py
+++ b/dissect/target/target.py
@@ -87,9 +87,10 @@ def __init__(self, path: Union[str, Path] = None):
         self._applied = False
 
         try:
-            self._config = config.load(self.path)
+            self._config = config.load([self.path, os.getcwd()])
         except Exception as e:
-            self.log.debug("Error loading config file", exc_info=e)
+            self.log.warning("Error loading config file: %s", self.path)
+            self.log.debug("", exc_info=e)
             self._config = config.load(None)  # This loads an empty config.
 
         # Fill the disks and/or volumes and/or filesystems and apply() will
diff --git a/dissect/target/tools/shell.py b/dissect/target/tools/shell.py
index 0b46b63f6..29b06781d 100644
--- a/dissect/target/tools/shell.py
+++ b/dissect/target/tools/shell.py
@@ -58,6 +58,7 @@
 except ImportError:
     # Readline is not available on Windows
     log.warning("Readline module is not available")
+    readline = None
 
 # ['mode', 'addr', 'dev', 'nlink', 'uid', 'gid', 'size', 'atime', 'mtime', 'ctime']
 STAT_TEMPLATE = """  File: {path} {symlink}
@@ -111,12 +112,43 @@ class TargetCmd(cmd.Cmd):
 
     CMD_PREFIX = "cmd_"
 
+    DEFAULT_HISTFILE = "~/.dissect_history"
+    DEFAULT_HISTFILESIZE = 10_000
+    DEFAULT_HISTDIR = None
+    DEFAULT_HISTDIRFMT = ".dissect_history_{uid}_{target}"
+
     def __init__(self, target: Target):
         cmd.Cmd.__init__(self)
         self.target = target
         self.debug = False
         self.identchars += "."
 
+        self.histfilesize = getattr(target._config, "HISTFILESIZE", self.DEFAULT_HISTFILESIZE)
+        self.histdir = getattr(target._config, "HISTDIR", self.DEFAULT_HISTDIR)
+
+        if self.histdir:
+            self.histdirfmt = getattr(target._config, "HISTDIRFMT", self.DEFAULT_HISTDIRFMT)
+            self.histfile = pathlib.Path(self.histdir).resolve() / pathlib.Path(
+                self.histdirfmt.format(uid=os.getuid(), target=target.name)
+            )
+        else:
+            self.histfile = pathlib.Path(getattr(target._config, "HISTFILE", self.DEFAULT_HISTFILE)).expanduser()
+
+    def preloop(self) -> None:
+        if readline and self.histfile.exists():
+            try:
+                readline.read_history_file(self.histfile)
+            except Exception as e:
+                log.debug("Error reading history file: %s", e)
+
+    def postloop(self) -> None:
+        if readline:
+            readline.set_history_length(self.histfilesize)
+            try:
+                readline.write_history_file(self.histfile)
+            except Exception as e:
+                log.debug("Error writing history file: %s", e)
+
     def __getattr__(self, attr: str) -> Any:
         if attr.startswith("help_"):
             _, _, command = attr.partition("_")
@@ -1241,10 +1273,11 @@ def run_cli(cli: cmd.Cmd) -> None:
             # Print an empty newline on exit
             print()
             return
+
         except KeyboardInterrupt:
             # Add a line when pressing ctrl+c, so the next one starts at a new line
             print()
-            pass
+
         except Exception as e:
             if cli.debug:
                 log.exception(e)
@@ -1252,7 +1285,6 @@ def run_cli(cli: cmd.Cmd) -> None:
                 log.info(e)
                 print(f"*** Unhandled error: {e}")
                 print("If you wish to see the full debug trace, enable debug mode.")
-            pass
 
 
 @catch_sigpipe