diff --git a/src/utils/rawconfig.py b/src/utils/rawconfig.py
index 1a514226..4fd4be96 100644
--- a/src/utils/rawconfig.py
+++ b/src/utils/rawconfig.py
@@ -3,7 +3,7 @@ from pathlib import Path
 from typing import List, Optional
 
 # External Packages
-from pydantic import BaseModel
+from pydantic import BaseModel, validator
 
 # Internal Packages
 from src.utils.helpers import to_snake_case_from_dash
@@ -14,17 +14,29 @@ class ConfigBase(BaseModel):
         allow_population_by_field_name = True
 
 class TextContentConfig(ConfigBase):
-    compressed_jsonl: Optional[Path]
-    input_files: Optional[List[str]]
+    input_files: Optional[List[Path]]
     input_filter: Optional[str]
-    embeddings_file: Optional[Path]
+    compressed_jsonl: Path
+    embeddings_file: Path
+
+    @validator('input_filter')
+    def input_filter_or_files_required(cls, input_filter, values, **kwargs):
+        if input_filter is None and ('input_files' not in values or values["input_files"] is None):
+            raise ValueError("Either input_filter or input_files required in all content-type.<text_search> section of Khoj config file")
+        return input_filter
 
 class ImageContentConfig(ConfigBase):
-    use_xmp_metadata: Optional[bool]
-    batch_size: Optional[int]
     input_directories: Optional[List[Path]]
     input_filter: Optional[str]
-    embeddings_file: Optional[Path]
+    embeddings_file: Path
+    use_xmp_metadata: bool
+    batch_size: int
+
+    @validator('input_filter')
+    def input_filter_or_directories_required(cls, input_filter, values, **kwargs):
+        if input_filter is None and ('input_directories' not in values or values["input_directories"] is None):
+            raise ValueError("Either input_filter or input_directories required in all content-type.image section of Khoj config file")
+        return input_filter
 
 class ContentConfig(ConfigBase):
     org: Optional[TextContentConfig]
@@ -34,12 +46,12 @@ class ContentConfig(ConfigBase):
     markdown: Optional[TextContentConfig]
 
 class TextSearchConfig(ConfigBase):
-    encoder: Optional[str]
-    cross_encoder: Optional[str]
+    encoder: str
+    cross_encoder: str
     model_directory: Optional[Path]
 
 class ImageSearchConfig(ConfigBase):
-    encoder: Optional[str]
+    encoder: str
     model_directory: Optional[Path]
 
 class SearchConfig(ConfigBase):
@@ -48,8 +60,8 @@ class SearchConfig(ConfigBase):
     image: Optional[ImageSearchConfig]
 
 class ConversationProcessorConfig(ConfigBase):
-    openai_api_key: Optional[str]
-    conversation_logfile: Optional[str]
+    openai_api_key: str
+    conversation_logfile: Path
 
 class ProcessorConfig(ConfigBase):
     conversation: Optional[ConversationProcessorConfig]
diff --git a/tests/test_cli.py b/tests/test_cli.py
index a266ebc0..5976dbdd 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -40,5 +40,5 @@ def test_cli_config_from_file():
     assert actual_args.config_file == Path('tests/data/config.yml')
     assert actual_args.regenerate == True
     assert actual_args.config is not None
-    assert actual_args.config.content_type.org.input_files == ['~/first_from_config.org', '~/second_from_config.org']
+    assert actual_args.config.content_type.org.input_files == [Path('~/first_from_config.org'), Path('~/second_from_config.org')]
     assert actual_args.verbose == 3