diff --git a/chatmastermind/main.py b/chatmastermind/main.py
index 1e41784..a57a8e2 100755
--- a/chatmastermind/main.py
+++ b/chatmastermind/main.py
@@ -3,6 +3,7 @@
 # vim: set fileencoding=utf-8 :
 
 import sys
+import os
 import argcomplete
 import argparse
 from pathlib import Path
@@ -156,6 +157,46 @@ def create_parser() -> argparse.ArgumentParser:
     return parser
 
 
+def create_directories(config: Config) -> None:  # noqa: 11
+    """
+    Create the directories in the given configuration if they don't exist.
+    """
+    def make_dir(path: Path) -> None:
+        try:
+            os.makedirs(path.absolute())
+        except Exception as e:
+            print(f"Creating directory '{path.absolute()}' failed with: {e}")
+            sys.exit(1)
+    # Cache
+    cache_path = Path(config.cache)
+    if not cache_path.exists():
+        answer = input(f"Cache directory '{cache_path}' does not exist. Create it? [y/n]")
+        if answer.lower() in ['y', 'yes']:
+            make_dir(cache_path.absolute())
+        else:
+            print("Can't continue without a valid cache directory!")
+            sys.exit(1)
+    # DB
+    db_path = Path(config.db)
+    if not db_path.exists():
+        answer = input(f"DB directory '{db_path}' does not exist. Create it? [y/n]")
+        if answer.lower() in ['y', 'yes']:
+            make_dir(db_path.absolute())
+        else:
+            print("Can't continue without a valid DB directory!")
+            sys.exit(1)
+    # Glossaries
+    if config.glossaries:
+        glossaries_path = Path(config.glossaries)
+        if not glossaries_path.exists():
+            answer = input(f"Glossaries directory '{glossaries_path}' does not exist. Create it? [y/n]")
+            if answer.lower() in ['y', 'yes']:
+                make_dir(glossaries_path.absolute())
+            else:
+                print("Can't continue without a valid glossaries directory. Create it or remove it from the configuration.")
+                sys.exit(1)
+
+
 def main() -> int:
     parser = create_parser()
     args = parser.parse_args()
@@ -165,6 +206,7 @@ def main() -> int:
         command.func(command)
     else:
         config = Config.from_file(args.config)
+        create_directories(config)
         command.func(command, config)
 
     return 0