Dspy Assertions

Enforce Constraints with dspy.Assert and dspy.Suggest

REMOVED IN DSPy 3.x. dspy.Assert and dspy.Suggest have been removed from the DSPy codebase (no assertions.py, no imports in __init__.py, retry.py commented out, no docs page). Use dspy.Refine or dspy.BestOfN instead — see /dspy-refine and /dspy-best-of-n. This skill documents the legacy API for maintaining existing codebases only.

Migration guide:

Old pattern	New equivalent
dspy.Assert(condition, msg) (hard rule, retry)	dspy.Refine(module, N=3, reward_fn=..., threshold=0.8)
dspy.Suggest(condition, msg) (soft rule, continue)	Lower weight in reward function (penalize but don't block)
max_backtrack_attempts=2	N=3 in Refine/BestOfN
DSPyAssertionError on exhaustion	fail_count parameter in Refine/BestOfN
Error message as feedback	Refine auto-generates feedback from reward scores

This skill documents the legacy dspy.Assert/dspy.Suggest APIs for users with existing DSPy 2.x code. For all new code, use /dspy-refine or /dspy-best-of-n — these are the DSPy 3.x replacements that work today.

Step 1 — Understand the user's situation

Determine which scenario applies before proceeding:

1. Maintaining a legacy DSPy 2.x codebase that already uses dspy.Assert/dspy.Suggest — use the legacy API reference below to understand behavior. The APIs work in DSPy 2.x only.
2. Migrating to DSPy 3.x and getting ImportError: cannot import name 'Assert' from 'dspy' — skip to the Migration section. Use dspy.Refine or dspy.BestOfN instead.
3. Writing new code — do not use Assert/Suggest at all. Go directly to /dspy-refine or /dspy-best-of-n.

Two kinds of constraints

import dspy

class QA(dspy.Module):
    def __init__(self):
        self.answer = dspy.ChainOfThought("question -> answer")

    def forward(self, question):
        result = self.answer(question=question)

        # Hard constraint — retries if violated
        dspy.Assert(
            len(result.answer) > 0,
            "Answer must not be empty",
        )

        # Soft constraint — logs warning but continues
        dspy.Suggest(
            len(result.answer.split()) >= 10,
            "Answer should be at least 10 words for completeness",
        )

        return result

dspy.Assert(condition, message)

Call dspy.Assert with a boolean condition and a message. When the condition is False, DSPy:

1. Catches the failure
2. Appends your message to the LM's context as feedback
3. Retries the LM call that produced the failing output
4. Repeats up to max_backtrack_attempts times (default: 2)
5. If all retries fail, raises DSPyAssertionError

dspy.Assert(
    result.answer != "I don't know",
    "You must provide a substantive answer based on the context",
)

Write specific messages. The message is injected back into the prompt on retry, so "Answer was 350 words, must be under 200" is far more useful than "too long."

dspy.Suggest(condition, message)

Same signature as Assert, but non-blocking. When the condition is False:

1. The message is logged as a warning
2. Execution continues normally
3. During optimization, suggestions guide the optimizer toward better prompts

dspy.Suggest(
    "however" not in result.answer.lower(),
    "Avoid hedging language like 'however' — be direct",
)

Use Suggest when the constraint improves quality but isn't a hard requirement.

How backtracking works

When dspy.Assert fails inside a module's forward(), DSPy doesn't just retry the same call. It modifies the signature by injecting the error message as additional context, so the LM has feedback about what went wrong:

# Original prompt (simplified)
Question: What is DSPy?
Answer: [LM generates here]

# After assertion failure, retry prompt becomes:
Question: What is DSPy?
Previous attempt failed: "Answer was 350 words, must be under 200. Be concise."
Answer: [LM generates here with feedback]

This is why assertion messages should be actionable instructions, not just error descriptions.

Targeting a specific module for backtracking

By default, DSPy backtracks to the most recent LM call. Use the backtrack_module parameter to target a specific module instead:

dspy.Assert(
    is_valid_json(result.output),
    "Output must be valid JSON. Check for missing braces or trailing commas.",
    backtrack_module=self.generate,  # retry this specific module
)

Common validation patterns

Length constraints

dspy.Assert(
    len(result.summary.split()) <= 50,
    f"Summary is {len(result.summary.split())} words, must be under 50",
)

Format validation

import re

dspy.Assert(
    re.match(r"^\d{4}-\d{2}-\d{2}$", result.date or ""),
    "Date must be in YYYY-MM-DD format",
)

Content checks

dspy.Assert(
    not any(phrase in result.answer.lower() for phrase in ["as an ai", "i cannot"]),
    "Do not include AI self-references in the answer",
)

List output validation

dspy.Assert(
    len(result.tags) >= 1,
    "Must assign at least one tag",
)
dspy.Assert(
    all(tag in VALID_TAGS for tag in result.tags),
    f"All tags must be from the valid set: {VALID_TAGS}",
)

Grounding in sources

# Check that the answer references at least one key term from the context
context_terms = set(word.lower() for p in context for word in p.split() if len(word) > 5)
answer_terms = set(word.lower() for word in result.answer.split())
overlap = context_terms & answer_terms
dspy.Assert(
    len(overlap) >= 3,
    "Answer must reference specific terms from the source passages",
)

Using assertions with optimizers

Assertions work with all DSPy optimizers. During optimization:

• dspy.Assert failures cause the training example to be retried. If the program can't satisfy the constraint after retries, that example is skipped.
• dspy.Suggest failures are tracked as soft signals. Optimizers like BootstrapFewShotWithRandomSearch and MIPROv2 prefer demo sets where suggestions are satisfied.

This means the optimizer learns prompts and demos that satisfy your constraints on the first try, reducing retries in production:

program = QA()

optimizer = dspy.BootstrapFewShotWithRandomSearch(
    metric=my_metric,
    max_bootstrapped_demos=4,
    num_candidate_programs=10,
)
optimized = optimizer.compile(program, trainset=trainset)

After optimization, the program will have few-shot demos that naturally produce outputs satisfying your assertions.

Catching assertion errors

When all retries are exhausted, dspy.Assert raises DSPyAssertionError. Handle it at the call site:

# DSPy 2.x only — this module does not exist in DSPy 3.x
from dspy.primitives.assertions import DSPyAssertionError

try:
    result = program(question="...")
except DSPyAssertionError as e:
    # Log the failure, return a fallback, etc.
    print(f"Output failed validation: {e}")

When to use Assert vs. Suggest

Rule of thumb: If a bad output reaching users would be a bug, use Assert. If it would just be suboptimal, use Suggest.

Migration to dspy.Refine / dspy.BestOfN

Assert/Suggest have been removed from DSPy 3.x. All constraint enforcement should use dspy.Refine (iterative with feedback) or dspy.BestOfN (independent sampling).

The key shift is from inline boolean checks to reward functions that score the full output:

# OLD (removed in DSPy 3.x)
dspy.Assert(len(result.answer.split()) <= 50, "Too long")
dspy.Suggest("however" not in result.answer, "Avoid hedging")

# NEW — reward function + Refine
def quality_reward(args, pred):
    score = 1.0
    if len(pred.answer.split()) > 50:      # hard rule
        score -= 0.4
    if "however" in pred.answer.lower():    # soft rule
        score -= 0.1
    return max(score, 0.0)

refined = dspy.Refine(module=my_module, N=3, reward_fn=quality_reward, threshold=0.8)

For full migration patterns, see /dspy-refine and /dspy-best-of-n.

Verify the migration by spot-checking your reward function before relying on it in production:

# Confirm reward function returns expected scores
print(quality_reward(None, valid_pred))    # should be >= threshold (e.g., 0.8)
print(quality_reward(None, invalid_pred))  # should be < threshold

Then run a sample call through the Refine/BestOfN wrapper and inspect result to confirm the output meets your constraints.

Gotchas

• Claude writes vague assertion messages like "Invalid output". The message is injected back into the LM prompt on retry — it IS the feedback. Write actionable instructions: "Summary is {len(words)} words, must be under 50. Remove examples and keep only the key conclusion." The more specific, the more likely the retry succeeds.
• Claude puts assertions outside forward(). dspy.Assert and dspy.Suggest only work inside a dspy.Module.forward() method because DSPy needs the module context for backtracking. Calling them at the top level or in a standalone function silently skips the retry mechanism.
• Claude uses Assert for style preferences. Hard assertions that fail after all retries raise DSPyAssertionError and crash the program. Use dspy.Suggest for subjective quality preferences (tone, style, verbosity) and reserve Assert for objective constraints (format validity, safety, schema compliance).
• Claude does not handle DSPyAssertionError at the call site. When all retry attempts are exhausted, Assert raises DSPyAssertionError. In production code, always wrap the program call in a try/except to handle validation failures gracefully with a fallback response.
• Claude chains too many assertions, making all retries fail. Each assertion that fails triggers a retry with feedback, but stacking 5+ strict assertions means the LM must satisfy all constraints simultaneously. If the success rate per constraint is 80%, five independent constraints yield ~33% joint success. Group related checks into one assertion with a combined message, or relax secondary constraints to Suggest.

Additional resources

• dspy.Refine API docs — recommended replacement for dspy.Assert (iterative improvement with feedback)
• dspy.BestOfN API docs — recommended replacement for dspy.Suggest patterns (sample N, pick best)
• reference.md — Legacy Assert/Suggest signatures, parameters, backtracking behavior, deprecation notes
• Note: the DSPy assertions guide (dspy.ai/learn/programming/7-assertions/) was removed from the docs along with the API in DSPy 3.x

Cross-references

Install any skill: npx skills add lebsral/DSPy-Programming-not-prompting-LMs-skills --skill <name>

• dspy.Refine (iterative improvement with feedback, recommended migration target) — see /dspy-refine
• dspy.BestOfN (independent sampling, pick best, replaces soft Suggest patterns) — see /dspy-best-of-n
• Problem-first framing with worked examples — see /ai-checking-outputs
• Stopping hallucinations with grounding and citations — see /ai-stopping-hallucinations
• Enforcing business rules and content policies — see /ai-following-rules
• Optimizers that learn to satisfy constraints — see /dspy-bootstrap-rs, /dspy-miprov2
• Install /ai-do if you do not have it — it routes any AI problem to the right skill and is the fastest way to work: npx skills add lebsral/DSPy-Programming-not-prompting-LMs-skills --skill ai-do