diff --git a/tdrs-backend/tdpservice/parsers/schema_defs/header.py b/tdrs-backend/tdpservice/parsers/schema_defs/header.py
index 9738c43eea..67475fd5f5 100644
--- a/tdrs-backend/tdpservice/parsers/schema_defs/header.py
+++ b/tdrs-backend/tdpservice/parsers/schema_defs/header.py
@@ -122,7 +122,11 @@
             startIndex=22,
             endIndex=23,
             required=True,
-            validators=[validators.matches("D")],
+            validators=[validators.matches("D",
+                                           error_func=lambda eargs: ("HEADER Update Indicator must be set to D "
+                                                                     f"instead of {eargs.value}. Please review "
+                                                                     "Exporting Complete Data Using FTANF in the "
+                                                                     "Knowledge Center."))],
         ),
     ],
 )
diff --git a/tdrs-backend/tdpservice/parsers/test/test_header.py b/tdrs-backend/tdpservice/parsers/test/test_header.py
index 78ffdfa21e..18079bc689 100644
--- a/tdrs-backend/tdpservice/parsers/test/test_header.py
+++ b/tdrs-backend/tdpservice/parsers/test/test_header.py
@@ -37,3 +37,37 @@ def test_header_cleanup(test_datafile):
 
     assert header_is_valid
     assert header_errors == []
+
+@pytest.mark.parametrize("header_line, is_valid, error", [
+    # Title error
+    ("      20204A06   TAN1ED", False, "Your file does not begin with a HEADER record."),
+    # quarter error
+    ("HEADER20205A06   TAN1ED", False, "HEADER Item 5 (quarter): 5 is not in [1, 2, 3, 4]."),
+    # Type error
+    ("HEADER20204E06   TAN1ED", False, "HEADER Item 6 (type): E is not in [A, C, G, S]."),
+    # Fips error
+    ("HEADER20204A07   TAN1ED", False, ("HEADER Item 1 (state fips): 07 is not in [00, 01, 02, 04, 05, 06, 08, 09, "
+                                        "10, 11, 12, 13, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, "
+                                        "30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 46, 47, 48, 49, "
+                                        "50, 51, 53, 54, 55, 56, 66, 72, 78].")),
+    # Tribe error
+    ("HEADER20204A00 -1TAN1ED", False, "HEADER Item 3 (tribe code):  -1 is not in range [0, 999]."),
+    # Program type error
+    ("HEADER20204A06   BAD1ED", False, "HEADER Item 7 (program type): BAD is not in [TAN, SSP]."),
+    # Edit error
+    ("HEADER20204A06   TAN3ED", False, "HEADER Item 8 (edit): 3 is not in [1, 2]."),
+    # Encryption error
+    ("HEADER20204A06   TAN1AD", False, "HEADER Item 9 (encryption): A is not in [ , E]."),
+    # Update error
+    ("HEADER20204A06   TAN1EA", False, ("HEADER Update Indicator must be set to D instead of A. Please review "
+                                        "Exporting Complete Data Using FTANF in the Knowledge Center.")),
+])
+@pytest.mark.django_db
+def test_header_fields(test_datafile, header_line, is_valid, error):
+    """Test validate all header fields."""
+    generate_error = util.make_generate_parser_error(test_datafile, 1)
+    header, header_is_valid, header_errors = schema_defs.header.parse_and_validate(header_line,
+                                                                                   generate_error)
+
+    assert is_valid == header_is_valid
+    assert error == header_errors[0].error_message
diff --git a/tdrs-backend/tdpservice/parsers/test/test_parse.py b/tdrs-backend/tdpservice/parsers/test/test_parse.py
index 1b20d897e0..41c02252bc 100644
--- a/tdrs-backend/tdpservice/parsers/test/test_parse.py
+++ b/tdrs-backend/tdpservice/parsers/test/test_parse.py
@@ -1581,7 +1581,10 @@ def test_parse_tanf_section_1_file_with_bad_update_indicator(tanf_section_1_file
     error = parser_errors.first()
 
     assert error.error_type == ParserErrorCategoryChoices.FIELD_VALUE
-    assert error.error_message == "HEADER Item 10 (update indicator): U does not match D."
+    assert error.error_message == ("HEADER Update Indicator must be set to D "
+                                   "instead of U. Please review "
+                                   "Exporting Complete Data Using FTANF in the "
+                                   "Knowledge Center.")
 
 
 @pytest.mark.django_db()
diff --git a/tdrs-backend/tdpservice/parsers/validators.py b/tdrs-backend/tdpservice/parsers/validators.py
index e8320055a5..2d4ac7b344 100644
--- a/tdrs-backend/tdpservice/parsers/validators.py
+++ b/tdrs-backend/tdpservice/parsers/validators.py
@@ -317,7 +317,7 @@ def matches(option, error_func=None):
     """Validate that value is equal to option."""
     return make_validator(
         lambda value: value == option,
-        lambda eargs: error_func(option)
+        lambda eargs: error_func(eargs)
         if error_func
         else f"{format_error_context(eargs)} {eargs.value} does not match {option}.",
     )