Block oversized requests before providers hard-fail

The runtime already tracked rough token estimates for compaction, but provider-bound
requests still relied on naive model output limits and could be sent upstream even
when the selected model could not fit the estimated prompt plus requested output.

This adds a small model token/context registry in the API layer, estimates request
size from the serialized prompt payload, and fails locally with a dedicated
context-window error before Anthropic or xAI calls are made. Focused integration
coverage asserts the preflight fires before any HTTP request leaves the process.

Constraint: Keep the first pass minimal and reusable across both Anthropic and OpenAI-compatible providers
Rejected: Auto-compact-and-retry in the same patch | broader control-flow change than the requested minimal preflight
Confidence: medium
Scope-risk: narrow
Reversibility: clean
Directive: Expand the model registry before enabling preflight for additional providers or aliases
Tested: cargo build -p api -p tools -p rusty-claude-cli; cargo test -p api
Not-tested: End-to-end CLI auto-compaction or retry behavior after a local context_window_blocked failure

rust/crates/api/src/error.rs

@@ -8,6 +8,13 @@ pub enum ApiError {
         provider: &'static str,
         env_vars: &'static [&'static str],
     },
+    ContextWindowExceeded {
+        model: String,
+        estimated_input_tokens: u32,
+        requested_output_tokens: u32,
+        estimated_total_tokens: u32,
+        context_window_tokens: u32,
+    },
     ExpiredOAuthToken,
     Auth(String),
     InvalidApiKeyEnv(VarError),
@@ -48,6 +55,7 @@ impl ApiError {
             Self::Api { retryable, .. } => *retryable,
             Self::RetriesExhausted { last_error, .. } => last_error.is_retryable(),
             Self::MissingCredentials { .. }
+            | Self::ContextWindowExceeded { .. }
             | Self::ExpiredOAuthToken
             | Self::Auth(_)
             | Self::InvalidApiKeyEnv(_)
@@ -67,6 +75,16 @@ impl Display for ApiError {
                 "missing {provider} credentials; export {} before calling the {provider} API",
                 env_vars.join(" or ")
             ),
+            Self::ContextWindowExceeded {
+                model,
+                estimated_input_tokens,
+                requested_output_tokens,
+                estimated_total_tokens,
+                context_window_tokens,
+            } => write!(
+                f,
+                "context_window_blocked for {model}: estimated input {estimated_input_tokens} + requested output {requested_output_tokens} = {estimated_total_tokens} tokens exceeds the {context_window_tokens}-token context window; compact the session or reduce request size before retrying"
+            ),
             Self::ExpiredOAuthToken => {
                 write!(
                     f,

rust/crates/api/src/providers/anthropic.rs

@@ -14,7 +14,7 @@ use telemetry::{AnalyticsEvent, AnthropicRequestProfile, ClientIdentity, Session
 use crate::error::ApiError;
 use crate::prompt_cache::{PromptCache, PromptCacheRecord, PromptCacheStats};
 
-use super::{Provider, ProviderFuture};
+use super::{preflight_message_request, Provider, ProviderFuture};
 use crate::sse::SseParser;
 use crate::types::{MessageDeltaEvent, MessageRequest, MessageResponse, StreamEvent, Usage};
 
@@ -294,6 +294,8 @@ impl AnthropicClient {
             }
         }
 
+        preflight_message_request(&request)?;
+
         let response = self.send_with_retry(&request).await?;
         let request_id = request_id_from_headers(response.headers());
         let mut response = response
@@ -337,6 +339,7 @@ impl AnthropicClient {
         &self,
         request: &MessageRequest,
     ) -> Result<MessageStream, ApiError> {
+        preflight_message_request(request)?;
         let response = self
             .send_with_retry(&request.clone().with_streaming())
             .await?;

rust/crates/api/src/providers/mod.rs

@@ -1,6 +1,8 @@
 use std::future::Future;
 use std::pin::Pin;
 
+use serde::Serialize;
+
 use crate::error::ApiError;
 use crate::types::{MessageRequest, MessageResponse};
 
@@ -40,6 +42,12 @@ pub struct ProviderMetadata {
     pub default_base_url: &'static str,
 }
 
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub struct ModelTokenLimit {
+    pub max_output_tokens: u32,
+    pub context_window_tokens: u32,
+}
+
 const MODEL_REGISTRY: &[(&str, ProviderMetadata)] = &[
     (
         "opus",
@@ -182,17 +190,86 @@ pub fn detect_provider_kind(model: &str) -> ProviderKind {
 
 #[must_use]
 pub fn max_tokens_for_model(model: &str) -> u32 {
+    model_token_limit(model).map_or_else(
+        || {
+            let canonical = resolve_model_alias(model);
+            if canonical.contains("opus") {
+                32_000
+            } else {
+                64_000
+            }
+        },
+        |limit| limit.max_output_tokens,
+    )
+}
+
+#[must_use]
+pub fn model_token_limit(model: &str) -> Option<ModelTokenLimit> {
     let canonical = resolve_model_alias(model);
-    if canonical.contains("opus") {
-        32_000
-    } else {
-        64_000
+    match canonical.as_str() {
+        "claude-opus-4-6" => Some(ModelTokenLimit {
+            max_output_tokens: 32_000,
+            context_window_tokens: 200_000,
+        }),
+        "claude-sonnet-4-6" | "claude-haiku-4-5-20251213" => Some(ModelTokenLimit {
+            max_output_tokens: 64_000,
+            context_window_tokens: 200_000,
+        }),
+        "grok-3" | "grok-3-mini" => Some(ModelTokenLimit {
+            max_output_tokens: 64_000,
+            context_window_tokens: 131_072,
+        }),
+        _ => None,
     }
 }
 
+pub fn preflight_message_request(request: &MessageRequest) -> Result<(), ApiError> {
+    let Some(limit) = model_token_limit(&request.model) else {
+        return Ok(());
+    };
+
+    let estimated_input_tokens = estimate_message_request_input_tokens(request);
+    let estimated_total_tokens = estimated_input_tokens.saturating_add(request.max_tokens);
+    if estimated_total_tokens > limit.context_window_tokens {
+        return Err(ApiError::ContextWindowExceeded {
+            model: resolve_model_alias(&request.model),
+            estimated_input_tokens,
+            requested_output_tokens: request.max_tokens,
+            estimated_total_tokens,
+            context_window_tokens: limit.context_window_tokens,
+        });
+    }
+
+    Ok(())
+}
+
+fn estimate_message_request_input_tokens(request: &MessageRequest) -> u32 {
+    let mut estimate = estimate_serialized_tokens(&request.messages);
+    estimate = estimate.saturating_add(estimate_serialized_tokens(&request.system));
+    estimate = estimate.saturating_add(estimate_serialized_tokens(&request.tools));
+    estimate = estimate.saturating_add(estimate_serialized_tokens(&request.tool_choice));
+    estimate
+}
+
+fn estimate_serialized_tokens<T: Serialize>(value: &T) -> u32 {
+    serde_json::to_vec(value)
+        .ok()
+        .map_or(0, |bytes| (bytes.len() / 4 + 1) as u32)
+}
+
 #[cfg(test)]
 mod tests {
-    use super::{detect_provider_kind, max_tokens_for_model, resolve_model_alias, ProviderKind};
+    use serde_json::json;
+
+    use crate::error::ApiError;
+    use crate::types::{
+        InputContentBlock, InputMessage, MessageRequest, ToolChoice, ToolDefinition,
+    };
+
+    use super::{
+        detect_provider_kind, max_tokens_for_model, model_token_limit, preflight_message_request,
+        resolve_model_alias, ProviderKind,
+    };
 
     #[test]
     fn resolves_grok_aliases() {
@@ -215,4 +292,86 @@ mod tests {
         assert_eq!(max_tokens_for_model("opus"), 32_000);
         assert_eq!(max_tokens_for_model("grok-3"), 64_000);
     }
+
+    #[test]
+    fn returns_context_window_metadata_for_supported_models() {
+        assert_eq!(
+            model_token_limit("claude-sonnet-4-6")
+                .expect("claude-sonnet-4-6 should be registered")
+                .context_window_tokens,
+            200_000
+        );
+        assert_eq!(
+            model_token_limit("grok-mini")
+                .expect("grok-mini should resolve to a registered model")
+                .context_window_tokens,
+            131_072
+        );
+    }
+
+    #[test]
+    fn preflight_blocks_requests_that_exceed_the_model_context_window() {
+        let request = MessageRequest {
+            model: "claude-sonnet-4-6".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(600_000),
+                }],
+            }],
+            system: Some("Keep the answer short.".to_string()),
+            tools: Some(vec![ToolDefinition {
+                name: "weather".to_string(),
+                description: Some("Fetches weather".to_string()),
+                input_schema: json!({
+                    "type": "object",
+                    "properties": { "city": { "type": "string" } },
+                }),
+            }]),
+            tool_choice: Some(ToolChoice::Auto),
+            stream: true,
+        };
+
+        let error = preflight_message_request(&request)
+            .expect_err("oversized request should be rejected before the provider call");
+
+        match error {
+            ApiError::ContextWindowExceeded {
+                model,
+                estimated_input_tokens,
+                requested_output_tokens,
+                estimated_total_tokens,
+                context_window_tokens,
+            } => {
+                assert_eq!(model, "claude-sonnet-4-6");
+                assert!(estimated_input_tokens > 136_000);
+                assert_eq!(requested_output_tokens, 64_000);
+                assert!(estimated_total_tokens > context_window_tokens);
+                assert_eq!(context_window_tokens, 200_000);
+            }
+            other => panic!("expected context-window preflight failure, got {other:?}"),
+        }
+    }
+
+    #[test]
+    fn preflight_skips_unknown_models() {
+        let request = MessageRequest {
+            model: "unknown-model".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(600_000),
+                }],
+            }],
+            system: None,
+            tools: None,
+            tool_choice: None,
+            stream: false,
+        };
+
+        preflight_message_request(&request)
+            .expect("models without context metadata should skip the guarded preflight");
+    }
 }

rust/crates/api/src/providers/openai_compat.rs

@@ -12,7 +12,7 @@ use crate::types::{
     ToolChoice, ToolDefinition, ToolResultContentBlock, Usage,
 };
 
-use super::{Provider, ProviderFuture};
+use super::{preflight_message_request, Provider, ProviderFuture};
 
 pub const DEFAULT_XAI_BASE_URL: &str = "https://api.x.ai/v1";
 pub const DEFAULT_OPENAI_BASE_URL: &str = "https://api.openai.com/v1";
@@ -128,6 +128,7 @@ impl OpenAiCompatClient {
             stream: false,
             ..request.clone()
         };
+        preflight_message_request(&request)?;
         let response = self.send_with_retry(&request).await?;
         let request_id = request_id_from_headers(response.headers());
         let payload = response.json::<ChatCompletionResponse>().await?;
@@ -142,6 +143,7 @@ impl OpenAiCompatClient {
         &self,
         request: &MessageRequest,
     ) -> Result<MessageStream, ApiError> {
+        preflight_message_request(request)?;
         let response = self
             .send_with_retry(&request.clone().with_streaming())
             .await?;

rust/crates/api/tests/client_integration.rs

@@ -103,6 +103,41 @@ async fn send_message_posts_json_and_parses_response() {
     );
 }
 
+#[tokio::test]
+async fn send_message_blocks_oversized_requests_before_the_http_call() {
+    let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));
+    let server = spawn_server(
+        state.clone(),
+        vec![http_response("200 OK", "application/json", "{}")],
+    )
+    .await;
+
+    let client = AnthropicClient::new("test-key").with_base_url(server.base_url());
+    let error = client
+        .send_message(&MessageRequest {
+            model: "claude-sonnet-4-6".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(600_000),
+                }],
+            }],
+            system: Some("Keep the answer short.".to_string()),
+            tools: None,
+            tool_choice: None,
+            stream: false,
+        })
+        .await
+        .expect_err("oversized request should fail local context-window preflight");
+
+    assert!(matches!(error, ApiError::ContextWindowExceeded { .. }));
+    assert!(
+        state.lock().await.is_empty(),
+        "preflight failure should avoid any upstream HTTP request"
+    );
+}
+
 #[tokio::test]
 async fn send_message_applies_request_profile_and_records_telemetry() {
     let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));

rust/crates/api/tests/openai_compat_integration.rs

@@ -4,10 +4,10 @@ use std::sync::Arc;
 use std::sync::{Mutex as StdMutex, OnceLock};
 
 use api::{
-    ContentBlockDelta, ContentBlockDeltaEvent, ContentBlockStartEvent, ContentBlockStopEvent,
-    InputContentBlock, InputMessage, MessageDeltaEvent, MessageRequest, OpenAiCompatClient,
-    OpenAiCompatConfig, OutputContentBlock, ProviderClient, StreamEvent, ToolChoice,
-    ToolDefinition,
+    ApiError, ContentBlockDelta, ContentBlockDeltaEvent, ContentBlockStartEvent,
+    ContentBlockStopEvent, InputContentBlock, InputMessage, MessageDeltaEvent, MessageRequest,
+    OpenAiCompatClient, OpenAiCompatConfig, OutputContentBlock, ProviderClient, StreamEvent,
+    ToolChoice, ToolDefinition,
 };
 use serde_json::json;
 use tokio::io::{AsyncReadExt, AsyncWriteExt};
@@ -63,6 +63,42 @@ async fn send_message_uses_openai_compatible_endpoint_and_auth() {
     assert_eq!(body["tools"][0]["type"], json!("function"));
 }
 
+#[tokio::test]
+async fn send_message_blocks_oversized_xai_requests_before_the_http_call() {
+    let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));
+    let server = spawn_server(
+        state.clone(),
+        vec![http_response("200 OK", "application/json", "{}")],
+    )
+    .await;
+
+    let client = OpenAiCompatClient::new("xai-test-key", OpenAiCompatConfig::xai())
+        .with_base_url(server.base_url());
+    let error = client
+        .send_message(&MessageRequest {
+            model: "grok-3".to_string(),
+            max_tokens: 64_000,
+            messages: vec![InputMessage {
+                role: "user".to_string(),
+                content: vec![InputContentBlock::Text {
+                    text: "x".repeat(300_000),
+                }],
+            }],
+            system: Some("Keep the answer short.".to_string()),
+            tools: None,
+            tool_choice: None,
+            stream: false,
+        })
+        .await
+        .expect_err("oversized request should fail local context-window preflight");
+
+    assert!(matches!(error, ApiError::ContextWindowExceeded { .. }));
+    assert!(
+        state.lock().await.is_empty(),
+        "preflight failure should avoid any upstream HTTP request"
+    );
+}
+
 #[tokio::test]
 async fn send_message_accepts_full_chat_completions_endpoint_override() {
     let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));