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Fix chat-to-proposal NLP gap: natural language now produces proposals#602

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Chris0Jeky merged 6 commits intomainfrom
fix/570-chat-nlp-proposal-gap
Mar 30, 2026
Merged

Fix chat-to-proposal NLP gap: natural language now produces proposals#602
Chris0Jeky merged 6 commits intomainfrom
fix/570-chat-nlp-proposal-gap

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Summary

Closes #570. Natural language chat messages that express actionable intent (e.g., "create new onboarding tasks for people who aren't technical") now produce proposals instead of failing with parse errors.

  • New NaturalLanguageInstructionExtractor: Bridges the gap between intent classification (which detects that a message is actionable) and instruction parsing (which requires structured syntax like create card "title"). When the classifier detects actionable intent, the extractor translates the natural language into structured instructions the regex parser can consume.
  • MockLlmProvider now produces Instructions when the classifier detects actionable intent, so ChatService passes structured instructions to the planner instead of raw natural language.
  • OpenAI and Gemini provider fallback paths also use the extractor when LLM-based structured JSON extraction fails and the static classifier is used as fallback.

What Changed

File Change
NaturalLanguageInstructionExtractor.cs New static class that extracts structured instructions from natural language given a detected intent
MockLlmProvider.cs Uses extractor to produce Instructions for actionable messages
OpenAiLlmProvider.cs Fallback paths (degraded + classifier fallback) now extract instructions
GeminiLlmProvider.cs Same fallback path improvements as OpenAI
NaturalLanguageInstructionExtractorTests.cs 38 unit tests covering all extraction paths

Test plan

  • 38 new unit tests for NaturalLanguageInstructionExtractor (quoted titles, natural language, card operations, board operations, edge cases)
  • All 47 existing MockLlmProvider/ChatService/OpenAi/Gemini tests pass unchanged
  • Full backend test suite passes: 1,737 tests, 0 failures
  • Manual verification: send "create new onboarding tasks for non-technical people" in a board-scoped chat session and verify a proposal is created

…arsing gap

When the intent classifier detects actionable intent in natural language
(e.g., "create new onboarding tasks"), this extractor produces structured
instructions (e.g., create card "Onboarding tasks") that the regex-based
parser can consume. This is the core fix for the #570 NLP gap.
…language

The Mock provider now uses NaturalLanguageInstructionExtractor when the
classifier detects actionable intent, producing Instructions that
ChatService can pass to the parser instead of the raw user message.
Fixes the core #570 scenario where natural language fails to produce proposals.
When OpenAI structured JSON parsing fails and the provider falls back to
the static classifier, also extract structured instructions so natural
language can still produce parseable instructions for the planner.
When Gemini structured JSON parsing fails and the provider falls back to
the static classifier, also extract structured instructions so natural
language can still produce parseable instructions for the planner.
Cover card create (quoted titles, natural language, various verbs),
card move/archive/update with IDs, board rename, edge cases (null,
empty, unknown intent), and title cleaning logic.
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Adversarial Self-Review

Issues Found and Fixed

Bug: ExtractBoardCreateInstructions outputs create card instead of board creation instruction.
In NaturalLanguageInstructionExtractor.ExtractBoardCreateInstructions, when a quoted name is found, the method returns create card "{name}" instead of a board creation instruction. This is wrong — it should either produce a board-specific instruction or return empty (since AutomationPlannerService doesn't have a "create board" pattern). The current behavior would create a card named after the board, which is misleading. Will fix to return empty (consistent with the comment already in the method).

Remaining Observations (Non-Blocking)

  1. Single-card limitation: The extractor always returns at most one instruction per message. Multi-card requests like "create cards for meeting setup, IT onboarding, HR orientation" still produce only one card. This is a known limitation tracked in Multi-instruction parsing for batch chat requests #574.

  2. CleanExtractedTitle uses non-compiled Regex: The Regex.Replace and Regex.IsMatch calls in CleanExtractedTitle are not compiled or pre-allocated. For the expected call frequency (chat messages), this is acceptable but could be optimized if performance becomes a concern.

  3. ColumnNameUnquotedPattern is declared but unused: The regex for unquoted column names is compiled but never referenced. This is dead code.

  4. CreateTitlePattern uses lazy (.+?) which may under-match: The pattern (.+?)\s*[.!?]?\s*$ with lazy quantifier will match the minimum possible, but the $ anchor forces it to the end of string anyway, so in practice it captures everything. This is correct but could be confusing to readers.

  5. No test for the RegexMatchTimeoutException catch path: The timeout path returns empty list gracefully, but there's no test proving this behavior.

  6. Existing ChatService NLP gap tests still assert old behavior: The test SendMessageAsync_NaturalLanguage_WithoutRequestProposal_NoProposalAttempt verifies that "can you create new onboarding tasks..." does NOT attempt a proposal. With the MockLlmProvider now extracting instructions and setting IsActionable=true, the classifier WILL detect this as actionable, and ChatService WILL attempt a proposal. This test may now fail — need to verify.

Action Items

  • Fix the ExtractBoardCreateInstructions bug
  • Remove unused ColumnNameUnquotedPattern
  • Verify/update the NLP gap test that expects no proposal attempt

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Code Review

This pull request introduces the NaturalLanguageInstructionExtractor service to convert natural language user messages into structured instructions compatible with the AutomationPlannerService. This extraction logic is integrated into the Gemini, OpenAI, and Mock LLM providers as a fallback mechanism when structured JSON parsing fails. Key feedback includes correcting a logic error where board creation incorrectly generated card creation instructions and utilizing a defined but unused regex pattern for unquoted column names in move operations.

{
var name = quotedMatch.Groups[1].Value.Trim();
if (!string.IsNullOrWhiteSpace(name))
return new List<string> { $"create card \"{name}\"" };
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high

The ExtractBoardCreateInstructions method incorrectly returns a create card instruction when the intent is board.create. Since the AutomationPlannerService does not currently support a create board command, this method should return an empty list to avoid creating unintended cards.

                return new List<string>();

Comment on lines +133 to +141
// Try quoted column name first
var columnMatch = ColumnNamePattern.Match(message);
if (columnMatch.Success)
{
var columnName = columnMatch.Groups[1].Value.Trim();
return new List<string> { $"move card {cardId} to column \"{columnName}\"" };
}

return new List<string>();
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medium

The ColumnNameUnquotedPattern regex is defined but not used. It should be integrated here as a fallback to support move instructions where the column name is not quoted (e.g., "move card {id} to column Done").

        // Try quoted column name first
        var columnMatch = ColumnNamePattern.Match(message);
        if (columnMatch.Success)
        {
            var columnName = columnMatch.Groups[1].Value.Trim();
            return new List<string> { $"move card {cardId} to column \"{columnName}\"" };
        }

        // Fallback to unquoted column name
        var unquotedMatch = ColumnNameUnquotedPattern.Match(message);
        if (unquotedMatch.Success)
        {
            var columnName = unquotedMatch.Groups[1].Value.Trim();
            return new List<string> { $"move card {cardId} to column \"{columnName}\"" };
        }

        return new List<string>();

ExtractBoardCreateInstructions incorrectly emitted create card instead
of returning empty (AutomationPlannerService has no board create parser
pattern). Also remove unused ColumnNameUnquotedPattern field.
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Self-Review Fixes Applied (commit 0087725)

  1. Fixed ExtractBoardCreateInstructions bug: Was incorrectly emitting create card "{name}" when it should return empty (no board create parser pattern exists). Now returns empty list.
  2. Removed unused ColumnNameUnquotedPattern: Dead code — the regex was compiled but never referenced.
  3. Verified existing ChatService NLP gap tests: The test SendMessageAsync_NaturalLanguage_WithoutRequestProposal_NoProposalAttempt still passes because it uses a mocked ILlmProvider that returns IsActionable: false, so the behavioral assertion (no planner call when not actionable and not requested) remains correct.

All 1,737 backend tests pass after fixes.

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Adversarial Code Review -- PR #602

1. [High] Injection via unquoted titles containing quote characters

File: NaturalLanguageInstructionExtractor.cs, lines ~88-96 (ExtractCardCreateInstructions)

When the CreateTitlePattern or NewTitlePattern branch extracts a title (not the QuotedTitlePattern branch), the raw captured text is run through CleanExtractedTitle but never sanitized for embedded quote characters. The output is then interpolated into create card "{title}".

Example input: create new task called "deploy to prod" today

  • CreateTitlePattern captures: task called "deploy to prod" today
  • CleanExtractedTitle does not strip quotes
  • Output: create card "Task called "deploy to prod" today"
  • AutomationPlannerService regex [^'""]+ will match only Task called (up to the first inner quote), silently truncating the title

This is a data corruption bug -- titles are silently mangled for any input containing quotes in the natural-language path.

Recommendation: Strip or escape embedded quote characters in CleanExtractedTitle, or reject titles that contain them.


2. [High] CleanExtractedTitle uses inline Regex.Replace without timeout -- ReDoS inconsistency

File: NaturalLanguageInstructionExtractor.cs, lines ~196-207

The static compiled regexes at the top of the class all correctly use TimeSpan.FromMilliseconds(200) timeout. However, CleanExtractedTitle calls Regex.Replace and Regex.IsMatch with inline patterns and no timeout:

title = Regex.Replace(title, @"\s+(please|plz|pls|thanks|thx|asap)\s*$", "", RegexOptions.IgnoreCase);
title = Regex.Replace(title, @"^(a|an|some|the|my|our)\s+", "", RegexOptions.IgnoreCase);
if (Regex.IsMatch(title, @"^(cards?|tasks?|items?)$", RegexOptions.IgnoreCase))

These particular patterns are simple alternations and unlikely to cause catastrophic backtracking in practice. However, this is inconsistent with the class's own stated defensive pattern (all other regexes use RegexTimeout). If these patterns are ever modified to be more complex, the lack of timeout becomes a real risk.

Recommendation: Use the existing RegexTimeout constant for consistency and defense-in-depth.


3. [Medium] column.reorder intent not handled -- silent instruction drop

File: NaturalLanguageInstructionExtractor.cs, line ~67

The Extract method switch handles: card.create, card.move, card.archive, card.update, board.create, board.update. However, LlmIntentClassifier.Classify also produces column.reorder (line 106 of LlmIntentClassifier.cs).

When a user says "reorder the columns on this board", the classifier returns (true, "column.reorder"), the extractor returns an empty list (default switch case), and the fallback in ChatService line 243 sends the raw natural language to the planner parser, which will fail. This is the same bug class that #570 fixes, just for a different intent.

Recommendation: Either handle column.reorder in the extractor or document it as a known gap.


4. [Medium] board.create always returns empty -- actionable intent produces no proposal

File: NaturalLanguageInstructionExtractor.cs, lines ~170-174

ExtractBoardCreateInstructions always returns an empty list with a comment saying the parser does not support it. But when the classifier detects board.create, IsActionable is true, the extractor returns empty, and ChatService falls back to sending raw natural language to the parser (line 243), which will fail.

The user sees: "I can help with that. I will create a proposal to board.create." followed by a parse error. This is misleading.

Recommendation: Either suppress the actionable flag for board.create when using static classification, or implement the instruction format.


5. [Medium] CardUpdateInstructions positional ambiguity between ID and quoted value

File: NaturalLanguageInstructionExtractor.cs, lines ~147-164

ExtractCardUpdateInstructions first matches a card ID via CardIdPattern, then uses QuotedTitlePattern to find the quoted value. But QuotedTitlePattern matches anywhere in the string and does not verify the quoted value appears after the card ID.

Example: For input rename "Sprint 5" on card 12345678-1234-1234-1234-123456789abc, the quoted match picks up "Sprint 5" and the card ID is found, but the field detection logic checks for "description" in the whole message. This could produce incorrect field/value pairings for unusual input orderings.


6. [Low] Test gap: no integration tests for the full ChatService path

The 38 tests validate the extractor in isolation. There are no integration tests verifying: ChatService.SendMessageAsync -> MockLlmProvider.CompleteAsync (now with Instructions) -> AutomationPlannerService.ParseInstructionAsync. An integration test sending natural language through the full pipeline would catch wiring bugs.


7. [Low] Test gap: no adversarial/fuzzy input tests

Missing test scenarios:

  • Inputs with embedded quotes in NL path (relates to issue 1)
  • Very long titles (1000+ chars)
  • Unicode titles
  • Mixed quote delimiters: input 'it's a test' with QuotedTitlePattern would match only it since the apostrophe terminates the single-quote match

8. [Low] Multi-card intent collapsed to single card creation

The classifier detects card.create for "create five new tasks for the sprint". The extractor produces a single create card "Tasks for the sprint". The user clearly intended multiple cards. Not a bug (better than producing nothing), but worth noting for follow-up.


Summary

# Severity Issue
1 High Embedded quotes in NL-extracted titles corrupt the instruction format
2 High CleanExtractedTitle inline regexes lack timeout (inconsistency)
3 Medium column.reorder intent not handled -- same bug class as #570
4 Medium board.create returns empty -- misleading promise with no proposal
5 Medium CardUpdateInstructions positional ambiguity
6 Low No integration test for full ChatService pipeline
7 Low No adversarial input tests
8 Low Multi-card intent collapsed to single card

Items 1-4 should be addressed before merge. Items 5-8 are acceptable as follow-up.

@Chris0Jeky Chris0Jeky merged commit 037cf29 into main Mar 30, 2026
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@Chris0Jeky Chris0Jeky deleted the fix/570-chat-nlp-proposal-gap branch March 30, 2026 23:09
@github-project-automation github-project-automation bot moved this from Pending to Done in Taskdeck Execution Mar 30, 2026
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Chat-to-proposal NLP gap: natural language fails to produce proposals

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