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Freedom251 › Blog › AI agents

What to Do When an AI Agent Gets Stuck, Makes Mistakes, or Repeats an Action

By Freedom251 Team · · 9 min read

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Stop the run long enough to establish its real state, inspect the last tool result or error, and check whether the requested change already happened. Then classify the failure: transient service problems can justify a limited retry; invalid input, credentials, permissions, or tool configuration require a correction; repeated actions require a stop condition; and sensitive or blocked work may need a human decision.

The sequence below works for developers and for people using consumer-facing agents, although the labels and controls differ between products. Do not blindly resubmit a failed request until you have checked for partial completion and possible side effects.

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What do I do when my AI agent gets stuck?

Use this order every time. It prevents the two most expensive recovery mistakes: repeating an action that already succeeded and retrying an error that cannot be fixed by waiting.

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  1. Pause and capture the current state. Save the visible task, run or session status, the latest turn, the last tool call, its arguments, the returned result, the exact error text, and any output already produced. In an API or SDK, record the structured error code and message rather than relying only on a shortened dashboard message.
  2. Check the target before replaying anything. Look at the file, record, message, deployment, ticket, database row, or other object the agent was supposed to change. A failed turn can still have created a file, sent a request, or changed a remote system. Compare the actual target with the intended end state and note which steps are complete.
  3. Determine whether the run is still active. A stream disconnect, browser refresh, or apparent stall does not necessarily mean the session failed. Retrieve the latest run or turn status if the product exposes it. If it is still running, wait for a terminal state or stop it safely; if it is complete, use the recorded result instead of starting a duplicate run.
  4. Classify the failure. Separate a temporary timeout, rate limit, or server failure from malformed input, expired credentials, missing permissions, an unavailable endpoint, a tool error, a failed session, or an approval pause. The remedy depends on this classification.
  5. Apply one bounded correction. Fix the invalid field, credential, permission, endpoint, tool argument, or instruction that caused the problem. For a suitable transient error, wait as directed by the service and retry with backoff. Set a maximum number of attempts or a deadline before you begin.
  6. Look for new evidence after each attempt. A retry is useful only when it produces a new result, a changed status, or information that narrows the cause. If the same call returns the same output, stop rather than escalating an accidental loop.
  7. Resume or escalate from the saved state. Continue unfinished work in the existing run when possible. Ask a person to decide when the next step is sensitive, ambiguous, irreversible, or blocked by missing information. Give support or an operator the IDs and evidence they need to investigate.

How to classify the failure before you retry

These categories are practical branches, not a universal error taxonomy. Products expose different status names, and many consumer interfaces do not show run, turn, or session identifiers.

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What you see First response Safe next step
Rate limit, timeout, temporary 5xx, or service unavailable Check whether the operation completed and read any server retry timing. Honor Retry-After when supplied; otherwise use exponential backoff with jitter and a maximum attempt count or deadline.
Invalid request or malformed parameters Read the field-level error and compare it with the tool contract. Correct the value or schema, then submit once. Replaying unchanged input will not repair it.
Credentials, permission, billing, or configuration failure Verify the identity, scopes, project, account, quota, and endpoint configuration. Fix access or configuration first; do not treat an authorization error as transient.
Tool error or unavailable endpoint Inspect the tool name, arguments, integration health, and returned payload. Repair or replace the tool, or return a clear failure to the agent so it can choose another valid path.
The agent repeats an action without progress Stop the loop and compare successive tool calls and results. Enforce an iteration limit, provide the missing environmental fact, change the approach, or ask a person.
Turn fails or a stream disconnects Retrieve the latest session or turn status and inspect saved work. Verify side effects and terminal status before resubmitting unfinished work.
Approval or safety-sensitive request Treat the pause as deliberate, not as a crash. Approve, reject, or clarify the action, then resume the saved run state.

How to tell whether the agent already completed the action

A tool call can reach its destination even when the model receives a timeout, disconnect, or malformed response. Before a replay, inspect the destination using an independent read operation where possible.

  • For files, check existence, modification time, size, and a content or checksum comparison.
  • For database or SaaS records, query the record by a stable identifier and inspect its audit history.
  • For messages or requests, check the provider’s sent, delivery, or job-status view.
  • For deployments or infrastructure changes, read the current resource configuration and deployment event rather than trusting the agent’s last sentence.
  • For payments, deletions, permission changes, or other irreversible effects, require an explicit human check before any retry.

Use an operation identifier, idempotency key, or destination-side deduplication when the service supports one. These mechanisms reduce duplicate effects, but they do not replace checking the actual target. The safe principle is to establish the present state first and ask the agent to perform only the missing transition.

Should you restart an AI agent after an error?

Not automatically. Restarting can discard useful context, duplicate side effects, or hide the original cause.

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Continue the existing run when

  • the session is healthy or merely waiting for a tool result;
  • the run has a resumable state and the missing step is clear;
  • an approval was requested and the decision can be supplied; or
  • a transient failure occurred and the operation has been verified as incomplete.

Start a new session only when

  • the session itself is reported failed or unrecoverable;
  • the cause of failure has been corrected; and
  • you have copied the relevant context, saved outputs, identifiers, and completed-step record into the new session.

A new session is not a fix for bad input, revoked credentials, an unavailable tool, or a missing approval. Correct the cause first, then resume the smallest unfinished unit of work.

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What to do when an agent keeps repeating the same action

Repetition usually means the agent is not receiving a reliable state change, cannot interpret the tool result, or has no stopping rule. Do not allow an unlimited loop.

  1. Stop at the configured limit. Set a maximum number of tool iterations, retries, or elapsed time. Anthropic’s engineering guidance describes maximum-iteration limits as a control for keeping agents bounded; Google’s troubleshooting guidance likewise recommends a maximum retry count.
  2. Compare calls, arguments, and results. Determine whether the arguments are identical, whether a supposedly successful result changed the environment, and whether the agent is seeing stale or ambiguous output.
  3. Check the tool contract. A tool should state what it does and return structured inputs and outputs. If success is represented only by vague text, the model may repeat the call because it cannot verify completion.
  4. Supply ground truth. Return the current state, error code, resource identifier, or fresh read result. Anthropic’s official engineering article puts the principle this way: “During execution, it’s crucial for the agents to gain “ground truth” from the environment at each step (such as tool call results or code execution) to assess its progress.”
  5. Change the plan or ask for help. If a valid tool cannot produce the needed state, switch to an available method or pause for a human. Repeating the same call is not a recovery strategy.

How to retry safely

Use backoff only for suitable transient failures

For a timeout, rate limit, or temporary server failure, wait before retrying and add random jitter so many workers do not retry simultaneously. Honor a server-provided Retry-After value. Define both an attempt limit and a time deadline; either one should end the retry loop.

Google’s current Gemini Python SDK documentation describes automatic retries of transient errors up to four times by default, with an initial delay of approximately one second and a maximum delay of 60 seconds. Those figures are implementation details for that SDK and version, not a cross-provider rule or a study statistic. Other SDKs and consumer products can behave differently, so inspect the relevant product’s current settings.

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Do not retry unchanged client errors

Malformed parameters, invalid model or tool names, expired credentials, missing permissions, quota or billing blocks, and policy rejections require a correction. Capture the error, fix the identified cause, and submit a new request only after the correction. If the message is unclear, reduce the request to a minimal reproducible call and inspect the tool’s schema and account configuration.

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Make external operations safe to replay

Before retrying a write, use an idempotency key or a natural unique key when the endpoint supports it. If it does not, read the target and design the next request around the observed state. For a non-idempotent action such as sending, charging, deleting, or granting access, a human should confirm the result before replay.

What developers should build into an agent

A clear tool contract

Document each tool’s purpose, required fields, allowed values, authentication assumptions, side effects, and success and failure schemas. Anthropic’s tool-use documentation emphasizes that the application executes client-side tools and sends their results back in a tool_result; the model does not execute that application code by itself. Your application therefore needs to validate inputs, execute the operation, and return an unambiguous result.

Observable state and tracing

Persist request, run, session, and turn identifiers; tool calls and results; status transitions; errors; approvals; and saved outputs. Operators should be able to answer what was attempted, what the environment did, and what remains without asking the model to reconstruct history from memory.

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Bounded execution

Wrap retries and agent loops with maximum attempts, deadlines, cancellation, and a clear terminal state. Emit a specific reason when the limit is reached, such as retry_limit_exceeded or awaiting_human_decision, rather than silently starting another turn.

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Human checkpoints

Require approval for sensitive tool calls, irreversible changes, ambiguous instructions, and blockers that cannot be resolved from available data. Save the run state while waiting. When the person responds, resume that state instead of creating a fresh task that might repeat earlier work.

Safe replay and recovery tests

Test timeout-after-commit, duplicate delivery, stale reads, revoked credentials, unavailable tools, malformed tool output, stream disconnects, and approval pauses. Verify that the recovery path reads the target state and continues from the first incomplete step.

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What if you are using a consumer-facing agent?

You may not see the underlying session or turn IDs. Translate the same controls into the interface you have:

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  1. Stop the current generation or automation if it is actively looping.
  2. Copy the visible error and note the task, time, and last displayed action.
  3. Check the target app, file, inbox, repository, or account for a partial change.
  4. Correct the prompt, attachment, login, permission, or connected-tool setting identified by the error.
  5. Resume only the unfinished step, stating what has already happened.
  6. If the agent still repeats or the action is sensitive, stop and contact the product’s support team with the error, timestamp, account or run identifier, and evidence of any side effect.

Not every consumer product supports resumable runs, approval workflows, idempotency keys, or detailed tracing. Where those controls are absent, manual verification and a smaller, reversible task are the safest substitutes.

When should you stop retrying and ask a person?

Escalate when the maximum retry or iteration limit is reached, the same result repeats without new evidence, the target state is uncertain, an external side effect may have occurred, credentials or permissions cannot be changed by the agent, the tool or endpoint remains unavailable, or the next action is legally, financially, or operationally sensitive.

Include the request, session, and turn IDs when available. Also provide the tool name, sanitized input, returned error, timestamps, current target state, completed actions, number of retries, and whether an external side effect occurred. This evidence lets an operator resume or compensate for the failed action instead of starting from an unreliable assumption.

A compact recovery checklist

  • Have I recorded the exact error and latest tool result?
  • Is the run still active, complete, paused for approval, or failed?
  • Did the target change despite the error?
  • Is the cause transient, invalid input, access, tool, state, or approval?
  • Will another attempt create a duplicate side effect?
  • What new evidence will this retry produce?
  • What is my retry count or deadline?
  • Can I resume the existing state, or has the session itself failed?
  • What information must a human receive if I stop?

The reliable habit is simple: observe first, classify second, correct or retry within limits, and resume only unfinished work. An agent that pauses with evidence is safer than one that appears busy while repeating an unverified action.

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