From ef0b5585d5170eabc850ac291b4f3d4dd14b85e3 Mon Sep 17 00:00:00 2001
From: Danny Kopping <danny@coder.com>
Date: Thu, 9 Jul 2026 15:36:56 +0200
Subject: [PATCH] feat: record and expose terminal upstream interception errors
 (#26961)

Categorises the terminal error of a failed interception and persists it
on the interception record, then surfaces it on the AI Gateway API.

- Categorise into an enum (`bad_request`, `unauthorized`,
  `rate_limited`, `overloaded`, `server_error`, `unknown`), unwrapping
  the ResponseError envelope, the upstream Anthropic/OpenAI SDK errors,
  and key-pool exhaustion so blocking and streaming paths agree.
- Thread the type and raw message through the recorder dRPC into the
  `aibridge_interceptions` row (optional proto fields; NULL on success).
- Expose the error on the AI Gateway thread API from the root
  interception.

*This PR was produced by opencode (agent) using the `anthropic/claude-opus-4-8` model, under human direction and review.*
---
 aibridge/api.go                               |   1 +
 aibridge/bridge.go                            |   5 +-
 .../intercept/chatcompletions/streaming.go    |   5 +-
 aibridge/intercept/messages/base.go           |   2 +-
 aibridge/intercept/messages/blocking.go       |   2 +-
 aibridge/intercept/messages/streaming.go      |   7 +-
 aibridge/interception_error.go                |  78 +++
 aibridge/interception_error_internal_test.go  | 127 ++++
 .../interception_error_internal_test.go       |  68 ++
 aibridge/internal/testutil/mockprovider.go    |   3 +
 aibridge/provider/anthropic.go                |  36 +-
 aibridge/provider/categorize_internal_test.go | 103 +++
 aibridge/provider/copilot.go                  |  10 +
 aibridge/provider/disabled.go                 |   3 +
 aibridge/provider/openai.go                   |  32 +
 aibridge/provider/provider.go                 |   7 +
 aibridge/recorder/types.go                    |  51 ++
 coderd/aibridged/proto/aibridged.pb.go        | 638 +++++++++---------
 coderd/aibridged/proto/aibridged.proto        |   6 +
 coderd/aibridged/translator.go                |  12 +-
 coderd/aibridgedserver/aibridgedserver.go     |  42 ++
 .../aibridgedserver/aibridgedserver_test.go   |  68 ++
 coderd/apidoc/docs.go                         |   8 +
 coderd/apidoc/swagger.json                    |   8 +
 coderd/database/db2sdk/db2sdk.go              |  11 +
 coderd/database/dbgen/dbgen.go                |   2 +
 coderd/database/querier_test.go               |  53 ++
 coderd/database/queries.sql.go                |  24 +-
 coderd/database/queries/aibridge.sql          |   6 +-
 codersdk/aibridge.go                          |   7 +
 docs/reference/api/aigateway.md               |   2 +
 docs/reference/api/schemas.md                 |   6 +
 enterprise/aibridged_integration_test.go      |  90 +++
 site/src/api/typesGenerated.ts                |  11 +
 34 files changed, 1212 insertions(+), 322 deletions(-)
 create mode 100644 aibridge/interception_error.go
 create mode 100644 aibridge/interception_error_internal_test.go
 create mode 100644 aibridge/internal/integrationtest/interception_error_internal_test.go
 create mode 100644 aibridge/provider/categorize_internal_test.go

diff --git a/aibridge/api.go b/aibridge/api.go
index b74912d565..587c2c38f7 100644
--- a/aibridge/api.go
+++ b/aibridge/api.go
@@ -34,6 +34,7 @@ type (
 	ModelThoughtRecord      = recorder.ModelThoughtRecord
 	Recorder                = recorder.Recorder
 	Metadata                = recorder.Metadata
+	ErrorType               = recorder.ErrorType
 
 	AnthropicConfig  = config.Anthropic
 	AWSBedrockConfig = config.AWSBedrock
diff --git a/aibridge/bridge.go b/aibridge/bridge.go
index 541a0bbf1b..5f3a5fbce9 100644
--- a/aibridge/bridge.go
+++ b/aibridge/bridge.go
@@ -355,12 +355,13 @@ func newInterceptionProcessor(p provider.Provider, cbs *circuitbreaker.ProviderC
 		// For a centralized pool, the hint now reflects the last key the
 		// failover loop attempted.
 		credCtx := intercept.WithCredentialInfo(ctx, cred)
+		errType, errMsg := categorizeInterceptionError(p, execErr)
 		if execErr != nil {
 			if m != nil {
 				m.InterceptionCount.WithLabelValues(p.Name(), interceptor.Model(), metrics.InterceptionCountStatusFailed, route, r.Method, actor.ID, string(client)).Add(1)
 			}
 			span.SetStatus(codes.Error, fmt.Sprintf("interception failed: %v", execErr))
-			log.Warn(credCtx, "interception failed", slog.Error(execErr))
+			log.Warn(credCtx, "interception failed", slog.Error(execErr), slog.F("error_type", string(errType)))
 		} else {
 			if m != nil {
 				m.InterceptionCount.WithLabelValues(p.Name(), interceptor.Model(), metrics.InterceptionCountStatusCompleted, route, r.Method, actor.ID, string(client)).Add(1)
@@ -371,6 +372,8 @@ func newInterceptionProcessor(p provider.Provider, cbs *circuitbreaker.ProviderC
 		_ = asyncRecorder.RecordInterceptionEnded(ctx, &recorder.InterceptionRecordEnded{
 			ID:             interceptor.ID().String(),
 			CredentialHint: cred.Hint(),
+			ErrorType:      errType,
+			ErrorMessage:   errMsg,
 		})
 
 		// Ensure all recording have completed before completing request.
diff --git a/aibridge/intercept/chatcompletions/streaming.go b/aibridge/intercept/chatcompletions/streaming.go
index 17ec61edbf..ccbe1d96ab 100644
--- a/aibridge/intercept/chatcompletions/streaming.go
+++ b/aibridge/intercept/chatcompletions/streaming.go
@@ -149,7 +149,10 @@ func (i *StreamingInterception) ProcessRequest(w http.ResponseWriter, r *http.Re
 				// client: as an SSE event if events have already been sent,
 				// or by direct write otherwise.
 				respErr := intercept.ResponseErrorFromKeyPool(keyPoolErr)
-				interceptionErr = respErr
+				// Record the underlying key-pool error (not the masked 502
+				// envelope) so the recorder can categorize by its kind. The
+				// client still receives respErr below.
+				interceptionErr = xerrors.Errorf("key pool exhausted: %w", keyPoolErr)
 				if events.IsStreaming() {
 					payload, mErr := i.marshalErr(respErr)
 					if mErr != nil {
diff --git a/aibridge/intercept/messages/base.go b/aibridge/intercept/messages/base.go
index b1e989b6a0..4eb8ef3a50 100644
--- a/aibridge/intercept/messages/base.go
+++ b/aibridge/intercept/messages/base.go
@@ -592,7 +592,7 @@ func ResponseErrorFromKeyPool(keyPoolErr *keypool.Error) *ResponseError {
 	}
 }
 
-func responseErrorFromAPIError(err error) *ResponseError {
+func ResponseErrorFromAPIError(err error) *ResponseError {
 	var apierr *anthropic.Error
 	if !errors.As(err, &apierr) {
 		return nil
diff --git a/aibridge/intercept/messages/blocking.go b/aibridge/intercept/messages/blocking.go
index 8b3d9cc613..cba8a30f0c 100644
--- a/aibridge/intercept/messages/blocking.go
+++ b/aibridge/intercept/messages/blocking.go
@@ -134,7 +134,7 @@ func (i *BlockingInterception) ProcessRequest(w http.ResponseWriter, r *http.Req
 				return xerrors.Errorf("key pool exhausted: %w", err)
 			}
 
-			if antErr := responseErrorFromAPIError(err); antErr != nil {
+			if antErr := ResponseErrorFromAPIError(err); antErr != nil {
 				i.writeUpstreamError(w, antErr)
 				return xerrors.Errorf("anthropic API error: %w", err)
 			}
diff --git a/aibridge/intercept/messages/streaming.go b/aibridge/intercept/messages/streaming.go
index 2369c17654..b4b9f69bbd 100644
--- a/aibridge/intercept/messages/streaming.go
+++ b/aibridge/intercept/messages/streaming.go
@@ -183,7 +183,10 @@ newStream:
 				// client: as an SSE event if events have already been sent,
 				// or by direct write otherwise.
 				respErr := ResponseErrorFromKeyPool(keyPoolErr)
-				interceptionErr = respErr
+				// Record the underlying key-pool error (not the masked 502
+				// envelope) so the recorder can categorize by its kind. The
+				// client still receives respErr below.
+				interceptionErr = xerrors.Errorf("key pool exhausted: %w", keyPoolErr)
 				if events.IsStreaming() {
 					payload, mErr := i.marshal(respErr)
 					if mErr != nil {
@@ -618,7 +621,7 @@ func (*StreamingInterception) mapStreamError(ctx context.Context, logger slog.Lo
 			// We can't reflect an error back if there's a connection error or the request context was canceled.
 			return nil
 		}
-		if antErr := responseErrorFromAPIError(streamErr); antErr != nil {
+		if antErr := ResponseErrorFromAPIError(streamErr); antErr != nil {
 			logger.Warn(ctx, "anthropic stream error", slog.Error(streamErr))
 			return antErr
 		}
diff --git a/aibridge/interception_error.go b/aibridge/interception_error.go
new file mode 100644
index 0000000000..e01a71b85d
--- /dev/null
+++ b/aibridge/interception_error.go
@@ -0,0 +1,78 @@
+package aibridge
+
+import (
+	"context"
+	"errors"
+	"strings"
+
+	"github.com/coder/coder/v2/aibridge/circuitbreaker"
+	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
+)
+
+// maxRecordedErrorMessageBytes caps the raw upstream error message persisted on
+// the interception record to avoid storing unbounded provider payloads.
+const maxRecordedErrorMessageBytes = 1024
+
+// errorCategorizer categorizes a provider's own terminal errors. It is
+// implemented by provider.Provider.
+type errorCategorizer interface {
+	CategorizeError(err error) *recorder.ErrorType
+}
+
+// categorizeInterceptionError maps a terminal interception error to a recorder
+// error type and a truncated raw message. It returns the empty ErrorType and an
+// empty message when err is nil (the interception succeeded).
+//
+// Provider-agnostic failures (circuit breaker, key-pool exhaustion) are handled
+// here; anything provider-specific is delegated to the provider, which owns the
+// knowledge of its SDK errors and response envelopes.
+func categorizeInterceptionError(c errorCategorizer, err error) (recorder.ErrorType, string) {
+	if err == nil {
+		return "", ""
+	}
+	msg := err.Error()
+	if len(msg) > maxRecordedErrorMessageBytes {
+		msg = strings.ToValidUTF8(msg[:maxRecordedErrorMessageBytes], "")
+	}
+
+	// Go context errors. These originate in the gateway or the caller, not
+	// upstream, so they are classified before any provider delegation.
+	switch {
+	case errors.Is(err, context.DeadlineExceeded):
+		return recorder.ErrorTypeTimeout, msg
+	case errors.Is(err, context.Canceled):
+		// The caller went away before the interception completed. This is not
+		// an upstream failure, but the interception did not succeed either, so
+		// it is recorded as unknown rather than dropped.
+		return recorder.ErrorTypeUnknown, msg
+	}
+
+	// Circuit breaker. It responds with 503 Service Unavailable when open, but
+	// returns a sentinel error that carries no HTTP status of its own.
+	if errors.Is(err, circuitbreaker.ErrCircuitOpen) {
+		return recorder.ErrorTypeServerError, msg
+	}
+
+	// Centralized key-pool failover. Checked before delegating because the pool
+	// masks the client response (e.g. permanent failures become 502), which
+	// would otherwise hide the cause.
+	var keyPoolErr *keypool.Error
+	if errors.As(err, &keyPoolErr) {
+		switch keyPoolErr.Kind {
+		case keypool.ErrorKindRateLimited:
+			return recorder.ErrorTypeRateLimited, msg
+		case keypool.ErrorKindPermanent:
+			return recorder.ErrorTypeUnauthorized, msg
+		default:
+			return recorder.ErrorTypeUnknown, msg
+		}
+	}
+
+	// Anything provider-specific is delegated to the provider, which owns the
+	// knowledge of its SDK errors and response envelopes.
+	if cat := c.CategorizeError(err); cat != nil {
+		return *cat, msg
+	}
+	return recorder.ErrorTypeUnknown, msg
+}
diff --git a/aibridge/interception_error_internal_test.go b/aibridge/interception_error_internal_test.go
new file mode 100644
index 0000000000..d5f08a2121
--- /dev/null
+++ b/aibridge/interception_error_internal_test.go
@@ -0,0 +1,127 @@
+package aibridge
+
+import (
+	"context"
+	"strings"
+	"testing"
+	"unicode/utf8"
+
+	"github.com/stretchr/testify/assert"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/aibridge/circuitbreaker"
+	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
+)
+
+// stubCategorizer is a test errorCategorizer standing in for a provider.
+type stubCategorizer struct {
+	result *recorder.ErrorType
+}
+
+func (s stubCategorizer) CategorizeError(error) *recorder.ErrorType {
+	return s.result
+}
+
+func ptr(t recorder.ErrorType) *recorder.ErrorType { return &t }
+
+func TestCategorizeInterceptionError(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		name     string
+		cat      stubCategorizer
+		err      error
+		wantType recorder.ErrorType
+		wantMsg  string
+	}{
+		{
+			name:     "nil success",
+			err:      nil,
+			wantType: "",
+			wantMsg:  "",
+		},
+		{
+			name:     "circuit open maps to server error",
+			err:      circuitbreaker.ErrCircuitOpen,
+			wantType: recorder.ErrorTypeServerError,
+			wantMsg:  circuitbreaker.ErrCircuitOpen.Error(),
+		},
+		{
+			name:     "context deadline is timeout",
+			err:      context.DeadlineExceeded,
+			wantType: recorder.ErrorTypeTimeout,
+			wantMsg:  context.DeadlineExceeded.Error(),
+		},
+		{
+			name:     "keypool permanent is unauthorized",
+			err:      &keypool.Error{Kind: keypool.ErrorKindPermanent},
+			wantType: recorder.ErrorTypeUnauthorized,
+			wantMsg:  (&keypool.Error{Kind: keypool.ErrorKindPermanent}).Error(),
+		},
+		{
+			name:     "keypool rate limited is rate limited",
+			err:      &keypool.Error{Kind: keypool.ErrorKindRateLimited},
+			wantType: recorder.ErrorTypeRateLimited,
+			wantMsg:  (&keypool.Error{Kind: keypool.ErrorKindRateLimited}).Error(),
+		},
+		{
+			name:     "keypool unrecognized kind is unknown",
+			err:      &keypool.Error{Kind: keypool.ErrorKind(-1)},
+			wantType: recorder.ErrorTypeUnknown,
+			wantMsg:  (&keypool.Error{Kind: keypool.ErrorKind(-1)}).Error(),
+		},
+		{
+			name:     "context canceled is unknown",
+			err:      context.Canceled,
+			wantType: recorder.ErrorTypeUnknown,
+			wantMsg:  context.Canceled.Error(),
+		},
+		{
+			name:     "wrapped keypool error is unwrapped",
+			err:      xerrors.Errorf("key pool exhausted: %w", &keypool.Error{Kind: keypool.ErrorKindPermanent}),
+			wantType: recorder.ErrorTypeUnauthorized,
+			wantMsg:  "key pool exhausted: all configured keys failed authentication",
+		},
+		{
+			name:     "delegated to provider",
+			cat:      stubCategorizer{result: ptr(recorder.ErrorTypeOverloaded)},
+			err:      xerrors.New("provider error"),
+			wantType: recorder.ErrorTypeOverloaded,
+			wantMsg:  "provider error",
+		},
+		{
+			name:     "provider does not recognize the error",
+			err:      xerrors.New("mystery"),
+			wantType: recorder.ErrorTypeUnknown,
+			wantMsg:  "mystery",
+		},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			gotType, gotMsg := categorizeInterceptionError(tc.cat, tc.err)
+			assert.Equal(t, tc.wantType, gotType)
+			assert.Equal(t, tc.wantMsg, gotMsg)
+		})
+	}
+}
+
+func TestCategorizeInterceptionErrorTruncatesMessage(t *testing.T) {
+	t.Parallel()
+
+	// ASCII: truncated exactly at the byte cap.
+	ascii := strings.Repeat("a", maxRecordedErrorMessageBytes*2)
+	_, gotMsg := categorizeInterceptionError(stubCategorizer{}, xerrors.New(ascii))
+	assert.Len(t, gotMsg, maxRecordedErrorMessageBytes)
+
+	// Multi-byte: the '€' rune (3 bytes) split at the cap is dropped, leaving
+	// valid UTF-8 just below the cap rather than an invalid trailing fragment.
+	multibyte := strings.Repeat("€", maxRecordedErrorMessageBytes)
+	_, gotMsg = categorizeInterceptionError(stubCategorizer{}, xerrors.New(multibyte))
+	assert.True(t, utf8.ValidString(gotMsg), "truncated message must stay valid UTF-8")
+	assert.Less(t, len(gotMsg), maxRecordedErrorMessageBytes)
+	assert.Positive(t, len(gotMsg))
+}
diff --git a/aibridge/internal/integrationtest/interception_error_internal_test.go b/aibridge/internal/integrationtest/interception_error_internal_test.go
new file mode 100644
index 0000000000..1f54fb2a93
--- /dev/null
+++ b/aibridge/internal/integrationtest/interception_error_internal_test.go
@@ -0,0 +1,68 @@
+package integrationtest
+
+import (
+	"io"
+	"net/http"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+	"github.com/tidwall/sjson"
+
+	"github.com/coder/coder/v2/aibridge/config"
+	"github.com/coder/coder/v2/aibridge/fixtures"
+	"github.com/coder/coder/v2/aibridge/internal/testutil"
+	"github.com/coder/coder/v2/aibridge/recorder"
+)
+
+// TestInterceptionUpstreamErrorRecorded verifies that a failed interception
+// records a categorized upstream error on the ended record.
+//
+// The default test provider is centralized (backed by a single-key pool), so a
+// 401 exhausts the pool. Both blocking and streaming interceptors preserve the
+// *keypool.Error so the cause is categorized as "unauthorized".
+func TestInterceptionUpstreamErrorRecorded(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		name      string
+		provider  string
+		fixture   []byte
+		path      string
+		streaming bool
+		wantType  recorder.ErrorType
+	}{
+		{"anthropic_blocking", config.ProviderAnthropic, fixtures.AntSimple, pathAnthropicMessages, false, recorder.ErrorTypeUnauthorized},
+		{"anthropic_streaming", config.ProviderAnthropic, fixtures.AntSimple, pathAnthropicMessages, true, recorder.ErrorTypeUnauthorized},
+		{"openai_blocking", config.ProviderOpenAI, fixtures.OaiChatSimple, pathOpenAIChatCompletions, false, recorder.ErrorTypeUnauthorized},
+		{"openai_streaming", config.ProviderOpenAI, fixtures.OaiChatSimple, pathOpenAIChatCompletions, true, recorder.ErrorTypeUnauthorized},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			fix := fixtures.Parse(t, tc.fixture)
+			upstream := testutil.NewMockUpstream(t.Context(), t,
+				testutil.NewErrorResponse(http.StatusUnauthorized, ""),
+			)
+			upstream.AllowOverflow = true
+
+			bridgeServer := newBridgeTestServer(t.Context(), t, upstream.URL, withProvider(tc.provider))
+
+			reqBody, err := sjson.SetBytes(fix.Request(), "stream", tc.streaming)
+			require.NoError(t, err)
+
+			resp, err := bridgeServer.makeRequest(t, http.MethodPost, tc.path, reqBody)
+			require.NoError(t, err)
+			_, _ = io.Copy(io.Discard, resp.Body)
+			require.NoError(t, resp.Body.Close())
+
+			intcs := bridgeServer.Recorder.RecordedInterceptions()
+			require.Len(t, intcs, 1)
+			ended := bridgeServer.Recorder.RecordedInterceptionEnd(intcs[0].ID)
+			require.NotNil(t, ended, "interception should be ended")
+			require.Equal(t, tc.wantType, ended.ErrorType)
+			require.NotEmpty(t, ended.ErrorMessage)
+		})
+	}
+}
diff --git a/aibridge/internal/testutil/mockprovider.go b/aibridge/internal/testutil/mockprovider.go
index a607ae68d0..df4fa1d150 100644
--- a/aibridge/internal/testutil/mockprovider.go
+++ b/aibridge/internal/testutil/mockprovider.go
@@ -10,6 +10,7 @@ import (
 	"github.com/coder/coder/v2/aibridge/config"
 	"github.com/coder/coder/v2/aibridge/intercept"
 	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
 	"github.com/coder/quartz"
 )
 
@@ -51,6 +52,8 @@ func (*MockProvider) KeyFailoverConfig(_ slog.Logger) keypool.KeyFailoverConfig
 }
 func (*MockProvider) CircuitBreakerConfig() *config.CircuitBreaker { return nil }
 func (*MockProvider) APIDumpDir() string                           { return "" }
+func (*MockProvider) CategorizeError(error) *recorder.ErrorType    { return nil }
+
 func (m *MockProvider) CreateInterceptor(w http.ResponseWriter, r *http.Request, tracer trace.Tracer) (intercept.Interceptor, error) {
 	if m.InterceptorFunc != nil {
 		return m.InterceptorFunc(w, r, tracer)
diff --git a/aibridge/provider/anthropic.go b/aibridge/provider/anthropic.go
index 3916e7c975..9424d4c960 100644
--- a/aibridge/provider/anthropic.go
+++ b/aibridge/provider/anthropic.go
@@ -2,6 +2,7 @@ package provider
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"net/http"
@@ -18,6 +19,7 @@ import (
 	"github.com/coder/coder/v2/aibridge/intercept"
 	"github.com/coder/coder/v2/aibridge/intercept/messages"
 	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
 	"github.com/coder/coder/v2/aibridge/tracing"
 	"github.com/coder/coder/v2/aibridge/utils"
 )
@@ -37,9 +39,13 @@ var anthropicOpenErrorResponse = func() []byte {
 	return []byte(`{"type":"error","error":{"type":"overloaded_error","message":"circuit breaker is open"}}`)
 }
 
+// statusOverloaded is the non-standard HTTP status Anthropic returns when its
+// API is overloaded. The net/http package does not define a constant for it.
+// https://platform.claude.com/docs/en/api/errors
+const statusOverloaded = 529
+
 var anthropicIsFailure = func(statusCode int) bool {
-	// https://platform.claude.com/docs/en/api/errors
-	if statusCode == 529 {
+	if statusCode == statusOverloaded {
 		return true
 	}
 	return circuitbreaker.DefaultIsFailure(statusCode)
@@ -215,3 +221,29 @@ func (p *Anthropic) CircuitBreakerConfig() *config.CircuitBreaker {
 func (p *Anthropic) APIDumpDir() string {
 	return p.cfg.APIDumpDir
 }
+
+func (*Anthropic) CategorizeError(err error) *recorder.ErrorType {
+	return categorizeAnthropicError(err)
+}
+
+// categorizeAnthropicError categorizes a terminal error from an Anthropic
+// (messages) provider. It returns nil when err is not an Anthropic-shaped error.
+func categorizeAnthropicError(err error) *recorder.ErrorType {
+	var status int
+	var envErr *messages.ResponseError
+	switch {
+	case errors.As(err, &envErr):
+		status = envErr.StatusCode
+	default:
+		apiErr := messages.ResponseErrorFromAPIError(err)
+		if apiErr == nil {
+			return nil
+		}
+		status = apiErr.StatusCode
+	}
+	t := recorder.ErrorTypeFromStatus(status)
+	if status == statusOverloaded {
+		t = recorder.ErrorTypeOverloaded
+	}
+	return &t
+}
diff --git a/aibridge/provider/categorize_internal_test.go b/aibridge/provider/categorize_internal_test.go
new file mode 100644
index 0000000000..4e78daadc5
--- /dev/null
+++ b/aibridge/provider/categorize_internal_test.go
@@ -0,0 +1,103 @@
+package provider
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/aibridge/intercept"
+	"github.com/coder/coder/v2/aibridge/intercept/messages"
+	"github.com/coder/coder/v2/aibridge/recorder"
+)
+
+func ptr(t recorder.ErrorType) *recorder.ErrorType { return &t }
+
+func TestAnthropicCategorizeError(t *testing.T) {
+	t.Parallel()
+
+	p := &Anthropic{}
+	cases := []struct {
+		name string
+		err  error
+		want *recorder.ErrorType
+	}{
+		{"overloaded", &messages.ResponseError{StatusCode: statusOverloaded}, ptr(recorder.ErrorTypeOverloaded)},
+		{"unauthorized", &messages.ResponseError{StatusCode: 401}, ptr(recorder.ErrorTypeUnauthorized)},
+		{"bad request", &messages.ResponseError{StatusCode: 400}, ptr(recorder.ErrorTypeBadRequest)},
+		{"not found is bad request", &messages.ResponseError{StatusCode: 404}, ptr(recorder.ErrorTypeBadRequest)},
+		{"payload too large is bad request", &messages.ResponseError{StatusCode: 413}, ptr(recorder.ErrorTypeBadRequest)},
+		{"timeout", &messages.ResponseError{StatusCode: 408}, ptr(recorder.ErrorTypeTimeout)},
+		{"server error", &messages.ResponseError{StatusCode: 503}, ptr(recorder.ErrorTypeServerError)},
+		{"not this provider", xerrors.New("mystery"), nil},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			assert.Equal(t, tc.want, p.CategorizeError(tc.err))
+		})
+	}
+}
+
+func TestCopilotCategorizeError(t *testing.T) {
+	t.Parallel()
+
+	// Copilot serves both OpenAI-compatible routes and an Anthropic-style
+	// /v1/messages route, so it tries the OpenAI shapes first and falls back to
+	// the Anthropic shapes.
+	p := &Copilot{}
+	cases := []struct {
+		name string
+		err  error
+		want *recorder.ErrorType
+	}{
+		// OpenAI envelope is categorized via the OpenAI path.
+		{"openai envelope unauthorized", &intercept.ResponseError{StatusCode: 401}, ptr(recorder.ErrorTypeUnauthorized)},
+		// A 529 in the OpenAI envelope is a generic 5xx (the OpenAI path has no
+		// "overloaded" notion), which proves the OpenAI path wins first.
+		{"openai envelope 529 is server error", &intercept.ResponseError{StatusCode: statusOverloaded}, ptr(recorder.ErrorTypeServerError)},
+		// Anthropic envelope falls through to the Anthropic path, where 529 is
+		// "overloaded".
+		{"anthropic envelope overloaded", &messages.ResponseError{StatusCode: statusOverloaded}, ptr(recorder.ErrorTypeOverloaded)},
+		{"anthropic envelope bad request", &messages.ResponseError{StatusCode: 400}, ptr(recorder.ErrorTypeBadRequest)},
+		{"neither provider", xerrors.New("mystery"), nil},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			assert.Equal(t, tc.want, p.CategorizeError(tc.err))
+		})
+	}
+}
+
+func TestOpenAICategorizeError(t *testing.T) {
+	t.Parallel()
+
+	p := &OpenAI{}
+	cases := []struct {
+		name string
+		err  error
+		want *recorder.ErrorType
+	}{
+		{"rate limited", &intercept.ResponseError{StatusCode: 429}, ptr(recorder.ErrorTypeRateLimited)},
+		{"unauthorized", &intercept.ResponseError{StatusCode: 403}, ptr(recorder.ErrorTypeUnauthorized)},
+		{"not found is bad request", &intercept.ResponseError{StatusCode: 404}, ptr(recorder.ErrorTypeBadRequest)},
+		{"unprocessable entity is bad request", &intercept.ResponseError{StatusCode: 422}, ptr(recorder.ErrorTypeBadRequest)},
+		{"timeout", &intercept.ResponseError{StatusCode: 408}, ptr(recorder.ErrorTypeTimeout)},
+		{"server error", &intercept.ResponseError{StatusCode: 500}, ptr(recorder.ErrorTypeServerError)},
+		// OpenAI returns 503 when its engine is overloaded.
+		{"503 is overloaded", &intercept.ResponseError{StatusCode: 503}, ptr(recorder.ErrorTypeOverloaded)},
+		// Anthropic's 529 is just another 5xx for OpenAI, not "overloaded".
+		{"529 is a generic server error", &intercept.ResponseError{StatusCode: statusOverloaded}, ptr(recorder.ErrorTypeServerError)},
+		{"not this provider", xerrors.New("mystery"), nil},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			assert.Equal(t, tc.want, p.CategorizeError(tc.err))
+		})
+	}
+}
diff --git a/aibridge/provider/copilot.go b/aibridge/provider/copilot.go
index d4e1691a62..79dc37ae4b 100644
--- a/aibridge/provider/copilot.go
+++ b/aibridge/provider/copilot.go
@@ -19,6 +19,7 @@ import (
 	"github.com/coder/coder/v2/aibridge/intercept/messages"
 	"github.com/coder/coder/v2/aibridge/intercept/responses"
 	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
 	"github.com/coder/coder/v2/aibridge/tracing"
 	"github.com/coder/coder/v2/aibridge/utils"
 )
@@ -121,6 +122,15 @@ func (p *Copilot) APIDumpDir() string {
 	return p.cfg.APIDumpDir
 }
 
+func (*Copilot) CategorizeError(err error) *recorder.ErrorType {
+	// Copilot serves both OpenAI-compatible routes and an Anthropic-style
+	// /v1/messages route, so fall back to the Anthropic shapes.
+	if t := categorizeOpenAIError(err); t != nil {
+		return t
+	}
+	return categorizeAnthropicError(err)
+}
+
 func (p *Copilot) CreateInterceptor(_ http.ResponseWriter, r *http.Request, tracer trace.Tracer) (_ intercept.Interceptor, outErr error) {
 	_, span := tracer.Start(r.Context(), "Intercept.CreateInterceptor")
 	defer tracing.EndSpanErr(span, &outErr)
diff --git a/aibridge/provider/disabled.go b/aibridge/provider/disabled.go
index fe0dfc3240..c49d45cdd0 100644
--- a/aibridge/provider/disabled.go
+++ b/aibridge/provider/disabled.go
@@ -10,6 +10,7 @@ import (
 	"github.com/coder/coder/v2/aibridge/config"
 	"github.com/coder/coder/v2/aibridge/intercept"
 	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
 )
 
 // DisabledStub is a Provider placeholder for a configured-but-disabled
@@ -42,6 +43,8 @@ func (*DisabledStub) KeyFailoverConfig(_ slog.Logger) keypool.KeyFailoverConfig
 }
 func (*DisabledStub) CircuitBreakerConfig() *config.CircuitBreaker { return nil }
 func (*DisabledStub) APIDumpDir() string                           { return "" }
+func (*DisabledStub) CategorizeError(error) *recorder.ErrorType    { return nil }
+
 func (*DisabledStub) CreateInterceptor(_ http.ResponseWriter, _ *http.Request, _ trace.Tracer) (intercept.Interceptor, error) {
 	//nolint:nilnil // disabled providers never reach the interceptor.
 	return nil, nil
diff --git a/aibridge/provider/openai.go b/aibridge/provider/openai.go
index 7ea4fe922e..0650ae66f9 100644
--- a/aibridge/provider/openai.go
+++ b/aibridge/provider/openai.go
@@ -2,6 +2,7 @@ package provider
 
 import (
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io"
 	"net/http"
@@ -18,6 +19,7 @@ import (
 	"github.com/coder/coder/v2/aibridge/intercept/chatcompletions"
 	"github.com/coder/coder/v2/aibridge/intercept/responses"
 	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
 	"github.com/coder/coder/v2/aibridge/tracing"
 	"github.com/coder/coder/v2/aibridge/utils"
 )
@@ -202,3 +204,33 @@ func (p *OpenAI) CircuitBreakerConfig() *config.CircuitBreaker {
 func (p *OpenAI) APIDumpDir() string {
 	return p.cfg.APIDumpDir
 }
+
+func (*OpenAI) CategorizeError(err error) *recorder.ErrorType {
+	return categorizeOpenAIError(err)
+}
+
+// categorizeOpenAIError categorizes a terminal error from an OpenAI-compatible
+// provider using the OpenAI response envelope and SDK error shapes. It returns
+// nil when err is not an OpenAI-shaped error.
+func categorizeOpenAIError(err error) *recorder.ErrorType {
+	var status int
+	var envErr *intercept.ResponseError
+	switch {
+	case errors.As(err, &envErr):
+		status = envErr.StatusCode
+	default:
+		apiErr := intercept.ResponseErrorFromAPIError(err)
+		if apiErr == nil {
+			return nil
+		}
+		status = apiErr.StatusCode
+	}
+	t := recorder.ErrorTypeFromStatus(status)
+	// OpenAI returns 503 when its engine is overloaded, which is a more
+	// explicit signal than a generic server error.
+	// https://developers.openai.com/api/docs/guides/error-codes#api-errors
+	if status == http.StatusServiceUnavailable {
+		t = recorder.ErrorTypeOverloaded
+	}
+	return &t
+}
diff --git a/aibridge/provider/provider.go b/aibridge/provider/provider.go
index 9afb2fe9b8..7706d83ab1 100644
--- a/aibridge/provider/provider.go
+++ b/aibridge/provider/provider.go
@@ -10,6 +10,7 @@ import (
 	"github.com/coder/coder/v2/aibridge/config"
 	"github.com/coder/coder/v2/aibridge/intercept"
 	"github.com/coder/coder/v2/aibridge/keypool"
+	"github.com/coder/coder/v2/aibridge/recorder"
 )
 
 var ErrUnknownRoute = xerrors.New("unknown route")
@@ -95,6 +96,12 @@ type Provider interface {
 	// CircuitBreakerConfig returns the circuit breaker configuration for the provider.
 	CircuitBreakerConfig() *config.CircuitBreaker
 
+	// CategorizeError maps a terminal upstream error produced by this provider
+	// (its SDK errors and response envelopes) to a recorder.ErrorType. It
+	// returns nil when the error is not recognized as one of this provider's,
+	// so the caller can fall back to provider-agnostic handling.
+	CategorizeError(err error) *recorder.ErrorType
+
 	// APIDumpDir returns the directory path for dumping API requests and responses.
 	// Empty string is returned when API dumping is not enabled.
 	APIDumpDir() string
diff --git a/aibridge/recorder/types.go b/aibridge/recorder/types.go
index 49269a31c5..a60b885bbf 100644
--- a/aibridge/recorder/types.go
+++ b/aibridge/recorder/types.go
@@ -2,6 +2,7 @@ package recorder
 
 import (
 	"context"
+	"net/http"
 	"time"
 )
 
@@ -55,12 +56,62 @@ type InterceptionRecord struct {
 	CredentialHint string
 }
 
+// ErrorType categorizes the terminal upstream error observed when an
+// interception fails. The empty value means the interception succeeded and no
+// error should be recorded. Values must match the
+// aibridge_interception_error_type Postgres enum.
+type ErrorType string
+
+const (
+	// ErrorTypeBadRequest is a malformed or otherwise rejected request (HTTP 400).
+	ErrorTypeBadRequest ErrorType = "bad_request"
+	// ErrorTypeUnauthorized is an authentication or authorization failure (HTTP 401/403).
+	ErrorTypeUnauthorized ErrorType = "unauthorized"
+	// ErrorTypeRateLimited is an upstream rate-limit response (HTTP 429).
+	ErrorTypeRateLimited ErrorType = "rate_limited"
+	// ErrorTypeOverloaded is an upstream overloaded response (Anthropic's HTTP
+	// 529 or OpenAI's HTTP 503).
+	ErrorTypeOverloaded ErrorType = "overloaded"
+	// ErrorTypeServerError is an upstream or gateway server error (HTTP 5xx).
+	ErrorTypeServerError ErrorType = "server_error"
+	// ErrorTypeTimeout is an upstream request timeout (HTTP 408).
+	ErrorTypeTimeout ErrorType = "timeout"
+	// ErrorTypeUnknown is any error that could not be categorized.
+	ErrorTypeUnknown ErrorType = "unknown"
+)
+
+// ErrorTypeFromStatus maps a standard upstream HTTP status code to an ErrorType.
+// Provider-specific statuses (e.g. Anthropic's 529) are handled by the provider
+// before calling this. Unrecognized codes yield ErrorTypeUnknown.
+func ErrorTypeFromStatus(status int) ErrorType {
+	switch status {
+	case http.StatusBadRequest, http.StatusNotFound, http.StatusRequestEntityTooLarge, http.StatusUnprocessableEntity:
+		return ErrorTypeBadRequest
+	case http.StatusUnauthorized, http.StatusForbidden:
+		return ErrorTypeUnauthorized
+	case http.StatusTooManyRequests:
+		return ErrorTypeRateLimited
+	case http.StatusRequestTimeout:
+		return ErrorTypeTimeout
+	}
+	if status >= 500 && status <= 599 {
+		return ErrorTypeServerError
+	}
+	return ErrorTypeUnknown
+}
+
 type InterceptionRecordEnded struct {
 	ID      string
 	EndedAt time.Time
 	// CredentialHint is the hint observed at end-of-interception.
 	// Only applied to the DB row for centralized; ignored for BYOK.
 	CredentialHint string
+	// ErrorType is the categorized terminal upstream error. Empty when the
+	// interception succeeded.
+	ErrorType ErrorType
+	// ErrorMessage is the raw terminal upstream error message. Empty when the
+	// interception succeeded.
+	ErrorMessage string
 }
 
 type TokenUsageRecord struct {
diff --git a/coderd/aibridged/proto/aibridged.pb.go b/coderd/aibridged/proto/aibridged.pb.go
index e1e82da4ed..fe68d6ee20 100644
--- a/coderd/aibridged/proto/aibridged.pb.go
+++ b/coderd/aibridged/proto/aibridged.pb.go
@@ -240,6 +240,12 @@ type RecordInterceptionEndedRequest struct {
 	Id             string                 `protobuf:"bytes,1,opt,name=id,proto3" json:"id,omitempty"` // UUID.
 	EndedAt        *timestamppb.Timestamp `protobuf:"bytes,2,opt,name=ended_at,json=endedAt,proto3" json:"ended_at,omitempty"`
 	CredentialHint string                 `protobuf:"bytes,3,opt,name=credential_hint,json=credentialHint,proto3" json:"credential_hint,omitempty"`
+	// error_type is the categorised terminal upstream error, absent when the
+	// interception succeeded. Matches the aibridge_interception_error_type enum.
+	ErrorType *string `protobuf:"bytes,4,opt,name=error_type,json=errorType,proto3,oneof" json:"error_type,omitempty"`
+	// error_message is the raw terminal upstream error message, absent when the
+	// interception succeeded.
+	ErrorMessage *string `protobuf:"bytes,5,opt,name=error_message,json=errorMessage,proto3,oneof" json:"error_message,omitempty"`
 }
 
 func (x *RecordInterceptionEndedRequest) Reset() {
@@ -295,6 +301,20 @@ func (x *RecordInterceptionEndedRequest) GetCredentialHint() string {
 	return ""
 }
 
+func (x *RecordInterceptionEndedRequest) GetErrorType() string {
+	if x != nil && x.ErrorType != nil {
+		return *x.ErrorType
+	}
+	return ""
+}
+
+func (x *RecordInterceptionEndedRequest) GetErrorMessage() string {
+	if x != nil && x.ErrorMessage != nil {
+		return *x.ErrorMessage
+	}
+	return ""
+}
+
 type RecordInterceptionEndedResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -1812,7 +1832,7 @@ var file_coderd_aibridged_proto_aibridged_proto_rawDesc = []byte{
 	0x6c, 0x5f, 0x73, 0x65, 0x71, 0x75, 0x65, 0x6e, 0x63, 0x65, 0x5f, 0x6e, 0x75, 0x6d, 0x62, 0x65,
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+	0xff, 0x01, 0x0a, 0x1e, 0x52, 0x65, 0x63, 0x6f, 0x72, 0x64, 0x49, 0x6e, 0x74, 0x65, 0x72, 0x63,
 	0x65, 0x70, 0x74, 0x69, 0x6f, 0x6e, 0x45, 0x6e, 0x64, 0x65, 0x64, 0x52, 0x65, 0x71, 0x75, 0x65,
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@@ -1821,313 +1841,320 @@ var file_coderd_aibridged_proto_aibridged_proto_rawDesc = []byte{
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+	0x65, 0x74, 0x4d, 0x43, 0x50, 0x53, 0x65, 0x72, 0x76, 0x65, 0x72, 0x41, 0x63, 0x63, 0x65, 0x73,
+	0x73, 0x54, 0x6f, 0x6b, 0x65, 0x6e, 0x73, 0x42, 0x61, 0x74, 0x63, 0x68, 0x52, 0x65, 0x73, 0x70,
+	0x6f, 0x6e, 0x73, 0x65, 0x32, 0xaa, 0x01, 0x0a, 0x0a, 0x41, 0x75, 0x74, 0x68, 0x6f, 0x72, 0x69,
+	0x7a, 0x65, 0x72, 0x12, 0x47, 0x0a, 0x0c, 0x49, 0x73, 0x41, 0x75, 0x74, 0x68, 0x6f, 0x72, 0x69,
+	0x7a, 0x65, 0x64, 0x12, 0x1a, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x49, 0x73, 0x41, 0x75,
+	0x74, 0x68, 0x6f, 0x72, 0x69, 0x7a, 0x65, 0x64, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a,
+	0x1b, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x49, 0x73, 0x41, 0x75, 0x74, 0x68, 0x6f, 0x72,
+	0x69, 0x7a, 0x65, 0x64, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x53, 0x0a, 0x10,
+	0x49, 0x73, 0x42, 0x75, 0x64, 0x67, 0x65, 0x74, 0x45, 0x78, 0x63, 0x65, 0x65, 0x64, 0x65, 0x64,
+	0x12, 0x1e, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x49, 0x73, 0x42, 0x75, 0x64, 0x67, 0x65,
+	0x74, 0x45, 0x78, 0x63, 0x65, 0x65, 0x64, 0x65, 0x64, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74,
+	0x1a, 0x1f, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x49, 0x73, 0x42, 0x75, 0x64, 0x67, 0x65,
+	0x74, 0x45, 0x78, 0x63, 0x65, 0x65, 0x64, 0x65, 0x64, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73,
+	0x65, 0x32, 0xbc, 0x01, 0x0a, 0x14, 0x50, 0x72, 0x6f, 0x76, 0x69, 0x64, 0x65, 0x72, 0x43, 0x6f,
+	0x6e, 0x66, 0x69, 0x67, 0x75, 0x72, 0x61, 0x74, 0x6f, 0x72, 0x12, 0x4d, 0x0a, 0x0e, 0x47, 0x65,
+	0x74, 0x41, 0x49, 0x50, 0x72, 0x6f, 0x76, 0x69, 0x64, 0x65, 0x72, 0x73, 0x12, 0x1c, 0x2e, 0x70,
+	0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x47, 0x65, 0x74, 0x41, 0x49, 0x50, 0x72, 0x6f, 0x76, 0x69, 0x64,
+	0x65, 0x72, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x1d, 0x2e, 0x70, 0x72, 0x6f,
+	0x74, 0x6f, 0x2e, 0x47, 0x65, 0x74, 0x41, 0x49, 0x50, 0x72, 0x6f, 0x76, 0x69, 0x64, 0x65, 0x72,
+	0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x55, 0x0a, 0x10, 0x57, 0x61, 0x74,
+	0x63, 0x68, 0x41, 0x49, 0x50, 0x72, 0x6f, 0x76, 0x69, 0x64, 0x65, 0x72, 0x73, 0x12, 0x1e, 0x2e,
+	0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x57, 0x61, 0x74, 0x63, 0x68, 0x41, 0x49, 0x50, 0x72, 0x6f,
+	0x76, 0x69, 0x64, 0x65, 0x72, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x1f, 0x2e,
+	0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x57, 0x61, 0x74, 0x63, 0x68, 0x41, 0x49, 0x50, 0x72, 0x6f,
+	0x76, 0x69, 0x64, 0x65, 0x72, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x30, 0x01,
+	0x42, 0x32, 0x5a, 0x30, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x63,
+	0x6f, 0x64, 0x65, 0x72, 0x2f, 0x63, 0x6f, 0x64, 0x65, 0x72, 0x2f, 0x76, 0x32, 0x2f, 0x63, 0x6f,
+	0x64, 0x65, 0x72, 0x64, 0x2f, 0x61, 0x69, 0x62, 0x72, 0x69, 0x64, 0x67, 0x65, 0x64, 0x2f, 0x70,
+	0x72, 0x6f, 0x74, 0x6f, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
@@ -2568,6 +2595,7 @@ func file_coderd_aibridged_proto_aibridged_proto_init() {
 		}
 	}
 	file_coderd_aibridged_proto_aibridged_proto_msgTypes[0].OneofWrappers = []interface{}{}
+	file_coderd_aibridged_proto_aibridged_proto_msgTypes[2].OneofWrappers = []interface{}{}
 	file_coderd_aibridged_proto_aibridged_proto_msgTypes[8].OneofWrappers = []interface{}{}
 	file_coderd_aibridged_proto_aibridged_proto_msgTypes[20].OneofWrappers = []interface{}{}
 	type x struct{}
diff --git a/coderd/aibridged/proto/aibridged.proto b/coderd/aibridged/proto/aibridged.proto
index f1c2657195..41795abdb9 100644
--- a/coderd/aibridged/proto/aibridged.proto
+++ b/coderd/aibridged/proto/aibridged.proto
@@ -83,6 +83,12 @@ message RecordInterceptionEndedRequest {
   string id = 1; // UUID.
   google.protobuf.Timestamp ended_at = 2;
   string credential_hint = 3;
+  // error_type is the categorised terminal upstream error, absent when the
+  // interception succeeded. Matches the aibridge_interception_error_type enum.
+  optional string error_type = 4;
+  // error_message is the raw terminal upstream error message, absent when the
+  // interception succeeded.
+  optional string error_message = 5;
 }
 
 message RecordInterceptionEndedResponse {}
diff --git a/coderd/aibridged/translator.go b/coderd/aibridged/translator.go
index ffad258538..81796c01f3 100644
--- a/coderd/aibridged/translator.go
+++ b/coderd/aibridged/translator.go
@@ -46,11 +46,19 @@ func (t *recorderTranslation) RecordInterception(ctx context.Context, req *aibri
 }
 
 func (t *recorderTranslation) RecordInterceptionEnded(ctx context.Context, req *aibridge.InterceptionRecordEnded) error {
-	_, err := t.client.RecordInterceptionEnded(ctx, &proto.RecordInterceptionEndedRequest{
+	endedReq := &proto.RecordInterceptionEndedRequest{
 		Id:             req.ID,
 		EndedAt:        timestamppb.New(req.EndedAt),
 		CredentialHint: req.CredentialHint,
-	})
+	}
+	if req.ErrorType != "" {
+		errType := string(req.ErrorType)
+		endedReq.ErrorType = &errType
+	}
+	if req.ErrorMessage != "" {
+		endedReq.ErrorMessage = &req.ErrorMessage
+	}
+	_, err := t.client.RecordInterceptionEnded(ctx, endedReq)
 	return err
 }
 
diff --git a/coderd/aibridgedserver/aibridgedserver.go b/coderd/aibridgedserver/aibridgedserver.go
index 29a1a08c35..cdfe739d02 100644
--- a/coderd/aibridgedserver/aibridgedserver.go
+++ b/coderd/aibridgedserver/aibridgedserver.go
@@ -258,10 +258,20 @@ func (s *Server) RecordInterceptionEnded(ctx context.Context, in *proto.RecordIn
 		)
 	}
 
+	// The error type and message form one logical unit: the terminal error.
+	// Gate the message on the type so the row never carries a message without a
+	// type (the migration treats both-NULL as a successful interception).
+	errType := interceptionErrorType(in.GetErrorType())
+	var errMsg sql.NullString
+	if errType.Valid && in.GetErrorMessage() != "" {
+		errMsg = sql.NullString{String: truncateErrorMessage(in.GetErrorMessage()), Valid: true}
+	}
 	_, err = s.store.UpdateAIBridgeInterceptionEnded(ctx, database.UpdateAIBridgeInterceptionEndedParams{
 		ID:             intcID,
 		EndedAt:        in.EndedAt.AsTime(),
 		CredentialHint: in.CredentialHint,
+		ErrorType:      errType,
+		ErrorMessage:   errMsg,
 	})
 	if err != nil {
 		return nil, xerrors.Errorf("end interception: %w", err)
@@ -994,6 +1004,38 @@ func credentialKindOrDefault(kind string) database.CredentialKind {
 	return ck
 }
 
+// maxErrorMessageBytes caps the interception error message stored in the
+// database, enforced at this trust boundary regardless of caller behavior.
+const maxErrorMessageBytes = 1024
+
+// truncateErrorMessage caps msg to maxErrorMessageBytes, dropping any partial
+// trailing rune so the stored value stays valid UTF-8.
+func truncateErrorMessage(msg string) string {
+	if len(msg) <= maxErrorMessageBytes {
+		return msg
+	}
+	return strings.ToValidUTF8(msg[:maxErrorMessageBytes], "")
+}
+
+// interceptionErrorType maps the wire error type onto the nullable DB enum. An
+// empty value yields NULL (a successful interception). A non-empty but
+// unrecognized value (e.g. version skew where the client knows an enum the DB
+// migration does not yet) is stored as 'unknown' rather than NULL, so the row's
+// error columns stay consistent with a recorded error_message.
+func interceptionErrorType(errType string) database.NullAIBridgeInterceptionErrorType {
+	if errType == "" {
+		return database.NullAIBridgeInterceptionErrorType{}
+	}
+	et := database.AIBridgeInterceptionErrorType(errType)
+	if !et.Valid() {
+		et = database.AibridgeInterceptionErrorTypeUnknown
+	}
+	return database.NullAIBridgeInterceptionErrorType{
+		AIBridgeInterceptionErrorType: et,
+		Valid:                         true,
+	}
+}
+
 func metadataToMap(in map[string]*anypb.Any) map[string]any {
 	meta := make(map[string]any, len(in))
 	for k, v := range in {
diff --git a/coderd/aibridgedserver/aibridgedserver_test.go b/coderd/aibridgedserver/aibridgedserver_test.go
index 0237b4db4c..b4eec74b66 100644
--- a/coderd/aibridgedserver/aibridgedserver_test.go
+++ b/coderd/aibridgedserver/aibridgedserver_test.go
@@ -1454,6 +1454,74 @@ func TestRecordInterceptionEnded(t *testing.T) {
 					}, nil)
 				},
 			},
+			{
+				name: "ok_with_error",
+				request: &proto.RecordInterceptionEndedRequest{
+					Id:           uuid.UUID{1}.String(),
+					EndedAt:      timestamppb.Now(),
+					ErrorType:    protobufproto.String(string(database.AibridgeInterceptionErrorTypeRateLimited)),
+					ErrorMessage: protobufproto.String("rate limited by upstream"),
+				},
+				setupMocks: func(t *testing.T, db *dbmock.MockStore, req *proto.RecordInterceptionEndedRequest) {
+					interceptionID, err := uuid.Parse(req.GetId())
+					assert.NoError(t, err, "parse interception UUID")
+
+					db.EXPECT().UpdateAIBridgeInterceptionEnded(gomock.Any(), database.UpdateAIBridgeInterceptionEndedParams{
+						ID:      interceptionID,
+						EndedAt: req.EndedAt.AsTime(),
+						ErrorType: database.NullAIBridgeInterceptionErrorType{
+							AIBridgeInterceptionErrorType: database.AIBridgeInterceptionErrorType(req.GetErrorType()),
+							Valid:                         true,
+						},
+						ErrorMessage: sql.NullString{String: req.GetErrorMessage(), Valid: true},
+					}).Return(database.AIBridgeInterception{ID: interceptionID}, nil)
+				},
+			},
+			{
+				name: "invalid_error_type_is_unknown",
+				request: &proto.RecordInterceptionEndedRequest{
+					Id:        uuid.UUID{1}.String(),
+					EndedAt:   timestamppb.Now(),
+					ErrorType: protobufproto.String("not-a-real-type"),
+				},
+				setupMocks: func(t *testing.T, db *dbmock.MockStore, req *proto.RecordInterceptionEndedRequest) {
+					interceptionID, err := uuid.Parse(req.GetId())
+					assert.NoError(t, err, "parse interception UUID")
+
+					// A non-empty but unrecognized error type is stored as
+					// 'unknown' (not NULL), keeping the error columns consistent.
+					db.EXPECT().UpdateAIBridgeInterceptionEnded(gomock.Any(), database.UpdateAIBridgeInterceptionEndedParams{
+						ID:      interceptionID,
+						EndedAt: req.EndedAt.AsTime(),
+						ErrorType: database.NullAIBridgeInterceptionErrorType{
+							AIBridgeInterceptionErrorType: database.AibridgeInterceptionErrorTypeUnknown,
+							Valid:                         true,
+						},
+					}).Return(database.AIBridgeInterception{ID: interceptionID}, nil)
+				},
+			},
+			{
+				name: "message_without_error_type_stores_neither",
+				request: &proto.RecordInterceptionEndedRequest{
+					Id:           uuid.UUID{1}.String(),
+					EndedAt:      timestamppb.Now(),
+					ErrorMessage: protobufproto.String("orphan message with no type"),
+				},
+				setupMocks: func(t *testing.T, db *dbmock.MockStore, req *proto.RecordInterceptionEndedRequest) {
+					interceptionID, err := uuid.Parse(req.GetId())
+					assert.NoError(t, err, "parse interception UUID")
+
+					// A message without a type is not a categorized error, so
+					// both columns stay NULL to preserve the both-NULL == success
+					// invariant rather than persisting a half-populated error.
+					db.EXPECT().UpdateAIBridgeInterceptionEnded(gomock.Any(), database.UpdateAIBridgeInterceptionEndedParams{
+						ID:           interceptionID,
+						EndedAt:      req.EndedAt.AsTime(),
+						ErrorType:    database.NullAIBridgeInterceptionErrorType{},
+						ErrorMessage: sql.NullString{},
+					}).Return(database.AIBridgeInterception{ID: interceptionID}, nil)
+				},
+			},
 			{
 				name: "bad_uuid_error",
 				request: &proto.RecordInterceptionEndedRequest{
diff --git a/coderd/apidoc/docs.go b/coderd/apidoc/docs.go
index f018cf7bc6..40e2ef73ce 100644
--- a/coderd/apidoc/docs.go
+++ b/coderd/apidoc/docs.go
@@ -15227,6 +15227,14 @@ const docTemplate = `{
                     "type": "string",
                     "format": "date-time"
                 },
+                "error_message": {
+                    "description": "ErrorMessage is the raw terminal upstream error message from the root\ninterception. Nil when the interception succeeded.",
+                    "type": "string"
+                },
+                "error_type": {
+                    "description": "ErrorType is the categorized terminal upstream error from the root\ninterception, or nil when the interception succeeded. See the\naibridge_interception_error_type enum for possible values.",
+                    "type": "string"
+                },
                 "id": {
                     "type": "string",
                     "format": "uuid"
diff --git a/coderd/apidoc/swagger.json b/coderd/apidoc/swagger.json
index 699d7805c9..314ac6bb40 100644
--- a/coderd/apidoc/swagger.json
+++ b/coderd/apidoc/swagger.json
@@ -13569,6 +13569,14 @@
 					"type": "string",
 					"format": "date-time"
 				},
+				"error_message": {
+					"description": "ErrorMessage is the raw terminal upstream error message from the root\ninterception. Nil when the interception succeeded.",
+					"type": "string"
+				},
+				"error_type": {
+					"description": "ErrorType is the categorized terminal upstream error from the root\ninterception, or nil when the interception succeeded. See the\naibridge_interception_error_type enum for possible values.",
+					"type": "string"
+				},
 				"id": {
 					"type": "string",
 					"format": "uuid"
diff --git a/coderd/database/db2sdk/db2sdk.go b/coderd/database/db2sdk/db2sdk.go
index cbb6107353..8fcf61c9d9 100644
--- a/coderd/database/db2sdk/db2sdk.go
+++ b/coderd/database/db2sdk/db2sdk.go
@@ -1281,6 +1281,17 @@ func buildAIBridgeThread(
 			n := rootIntc.AgentFirewallSequenceNumber.Int32
 			thread.AgentFirewallSequenceNumber = &n
 		}
+		// Surface the terminal upstream error from the root interception. The
+		// message is only meaningful alongside a type, so it is nested to avoid
+		// a half-populated error on the response.
+		if rootIntc.ErrorType.Valid {
+			errType := string(rootIntc.ErrorType.AIBridgeInterceptionErrorType)
+			thread.ErrorType = &errType
+			if rootIntc.ErrorMessage.Valid {
+				errMsg := rootIntc.ErrorMessage.String
+				thread.ErrorMessage = &errMsg
+			}
+		}
 	}
 
 	// Compute thread time bounds from interceptions.
diff --git a/coderd/database/dbgen/dbgen.go b/coderd/database/dbgen/dbgen.go
index 782e004e6b..cd4bec9ba6 100644
--- a/coderd/database/dbgen/dbgen.go
+++ b/coderd/database/dbgen/dbgen.go
@@ -2022,6 +2022,8 @@ func AIBridgeInterception(t testing.TB, db database.Store, seed database.InsertA
 			ID:             interception.ID,
 			EndedAt:        *endedAt,
 			CredentialHint: takeFirst(seed.CredentialHint, ""),
+			ErrorType:      database.NullAIBridgeInterceptionErrorType{},
+			ErrorMessage:   sql.NullString{},
 		})
 		require.NoError(t, err, "insert aibridge interception")
 	}
diff --git a/coderd/database/querier_test.go b/coderd/database/querier_test.go
index 00afbbd34f..008b6ef4db 100644
--- a/coderd/database/querier_test.go
+++ b/coderd/database/querier_test.go
@@ -11037,6 +11037,59 @@ func TestUpdateAIBridgeInterceptionEnded(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, "sk-u...byok", updated.CredentialHint)
 	})
+
+	t.Run("ErrorRecorded", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		user := dbgen.User(t, db, database.User{})
+		intc, err := db.InsertAIBridgeInterception(ctx, database.InsertAIBridgeInterceptionParams{
+			ID:             uuid.New(),
+			InitiatorID:    user.ID,
+			Metadata:       json.RawMessage("{}"),
+			CredentialKind: database.CredentialKindCentralized,
+		})
+		require.NoError(t, err)
+		require.False(t, intc.ErrorType.Valid)
+		require.False(t, intc.ErrorMessage.Valid)
+
+		updated, err := db.UpdateAIBridgeInterceptionEnded(ctx, database.UpdateAIBridgeInterceptionEndedParams{
+			ID:      intc.ID,
+			EndedAt: time.Now(),
+			ErrorType: database.NullAIBridgeInterceptionErrorType{
+				AIBridgeInterceptionErrorType: database.AibridgeInterceptionErrorTypeOverloaded,
+				Valid:                         true,
+			},
+			ErrorMessage: sql.NullString{String: "upstream overloaded", Valid: true},
+		})
+		require.NoError(t, err)
+		require.True(t, updated.ErrorType.Valid)
+		require.Equal(t, database.AibridgeInterceptionErrorTypeOverloaded, updated.ErrorType.AIBridgeInterceptionErrorType)
+		require.True(t, updated.ErrorMessage.Valid)
+		require.Equal(t, "upstream overloaded", updated.ErrorMessage.String)
+	})
+
+	t.Run("NoErrorLeavesColumnsNull", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		user := dbgen.User(t, db, database.User{})
+		intc, err := db.InsertAIBridgeInterception(ctx, database.InsertAIBridgeInterceptionParams{
+			ID:             uuid.New(),
+			InitiatorID:    user.ID,
+			Metadata:       json.RawMessage("{}"),
+			CredentialKind: database.CredentialKindCentralized,
+		})
+		require.NoError(t, err)
+
+		updated, err := db.UpdateAIBridgeInterceptionEnded(ctx, database.UpdateAIBridgeInterceptionEndedParams{
+			ID:      intc.ID,
+			EndedAt: time.Now(),
+		})
+		require.NoError(t, err)
+		require.False(t, updated.ErrorType.Valid)
+		require.False(t, updated.ErrorMessage.Valid)
+	})
 }
 
 func TestAIBridgeInterceptionAgentFirewallColumns(t *testing.T) {
diff --git a/coderd/database/queries.sql.go b/coderd/database/queries.sql.go
index 16b5c89bea..885f2a8b54 100644
--- a/coderd/database/queries.sql.go
+++ b/coderd/database/queries.sql.go
@@ -2402,21 +2402,33 @@ UPDATE aibridge_interceptions
 		credential_hint = CASE
 			WHEN credential_kind = 'centralized' THEN $2::text
 			ELSE credential_hint
-		END
+		END,
+		-- Terminal upstream error, only set when the interception failed.
+		-- NULL leaves the columns empty for successful interceptions.
+		error_type = $3::aibridge_interception_error_type,
+		error_message = $4::text
 WHERE
-	id = $3::uuid
+	id = $5::uuid
 	AND ended_at IS NULL
 RETURNING id, initiator_id, provider, model, started_at, metadata, ended_at, api_key_id, client, thread_parent_id, thread_root_id, client_session_id, session_id, provider_name, credential_kind, credential_hint, agent_firewall_session_id, agent_firewall_sequence_number, error_type, error_message
 `
 
 type UpdateAIBridgeInterceptionEndedParams struct {
-	EndedAt        time.Time `db:"ended_at" json:"ended_at"`
-	CredentialHint string    `db:"credential_hint" json:"credential_hint"`
-	ID             uuid.UUID `db:"id" json:"id"`
+	EndedAt        time.Time                         `db:"ended_at" json:"ended_at"`
+	CredentialHint string                            `db:"credential_hint" json:"credential_hint"`
+	ErrorType      NullAIBridgeInterceptionErrorType `db:"error_type" json:"error_type"`
+	ErrorMessage   sql.NullString                    `db:"error_message" json:"error_message"`
+	ID             uuid.UUID                         `db:"id" json:"id"`
 }
 
 func (q *sqlQuerier) UpdateAIBridgeInterceptionEnded(ctx context.Context, arg UpdateAIBridgeInterceptionEndedParams) (AIBridgeInterception, error) {
-	row := q.db.QueryRowContext(ctx, updateAIBridgeInterceptionEnded, arg.EndedAt, arg.CredentialHint, arg.ID)
+	row := q.db.QueryRowContext(ctx, updateAIBridgeInterceptionEnded,
+		arg.EndedAt,
+		arg.CredentialHint,
+		arg.ErrorType,
+		arg.ErrorMessage,
+		arg.ID,
+	)
 	var i AIBridgeInterception
 	err := row.Scan(
 		&i.ID,
diff --git a/coderd/database/queries/aibridge.sql b/coderd/database/queries/aibridge.sql
index 3e60ccda28..1c396cc690 100644
--- a/coderd/database/queries/aibridge.sql
+++ b/coderd/database/queries/aibridge.sql
@@ -15,7 +15,11 @@ UPDATE aibridge_interceptions
 		credential_hint = CASE
 			WHEN credential_kind = 'centralized' THEN @credential_hint::text
 			ELSE credential_hint
-		END
+		END,
+		-- Terminal upstream error, only set when the interception failed.
+		-- NULL leaves the columns empty for successful interceptions.
+		error_type = sqlc.narg('error_type')::aibridge_interception_error_type,
+		error_message = sqlc.narg('error_message')::text
 WHERE
 	id = @id::uuid
 	AND ended_at IS NULL
diff --git a/codersdk/aibridge.go b/codersdk/aibridge.go
index e7e54791bd..7b92638ac5 100644
--- a/codersdk/aibridge.go
+++ b/codersdk/aibridge.go
@@ -123,6 +123,13 @@ type AIBridgeThread struct {
 	EndedAt        *time.Time                       `json:"ended_at,omitempty" format:"date-time"`
 	TokenUsage     AIBridgeSessionThreadsTokenUsage `json:"token_usage"`
 	AgenticActions []AIBridgeAgenticAction          `json:"agentic_actions"`
+	// ErrorType is the categorized terminal upstream error from the root
+	// interception, or nil when the interception succeeded. See the
+	// aibridge_interception_error_type enum for possible values.
+	ErrorType *string `json:"error_type,omitempty"`
+	// ErrorMessage is the raw terminal upstream error message from the root
+	// interception. Nil when the interception succeeded.
+	ErrorMessage *string `json:"error_message,omitempty"`
 	// AgentFirewallSessionID links this thread to an agent firewall
 	// confinement session. Nil when the request did not pass through
 	// the agent firewall.
diff --git a/docs/reference/api/aigateway.md b/docs/reference/api/aigateway.md
index 87bcfc6afc..9c2f3bd853 100644
--- a/docs/reference/api/aigateway.md
+++ b/docs/reference/api/aigateway.md
@@ -240,6 +240,8 @@ Alias: also available at /api/v2/aibridge/sessions/{session_id} for backward com
       "credential_hint": "string",
       "credential_kind": "string",
       "ended_at": "2019-08-24T14:15:22Z",
+      "error_message": "string",
+      "error_type": "string",
       "id": "497f6eca-6276-4993-bfeb-53cbbbba6f08",
       "model": "string",
       "prompt": "string",
diff --git a/docs/reference/api/schemas.md b/docs/reference/api/schemas.md
index d374d10e11..e484ff2fe2 100644
--- a/docs/reference/api/schemas.md
+++ b/docs/reference/api/schemas.md
@@ -697,6 +697,8 @@
       "credential_hint": "string",
       "credential_kind": "string",
       "ended_at": "2019-08-24T14:15:22Z",
+      "error_message": "string",
+      "error_type": "string",
       "id": "497f6eca-6276-4993-bfeb-53cbbbba6f08",
       "model": "string",
       "prompt": "string",
@@ -836,6 +838,8 @@
   "credential_hint": "string",
   "credential_kind": "string",
   "ended_at": "2019-08-24T14:15:22Z",
+  "error_message": "string",
+  "error_type": "string",
   "id": "497f6eca-6276-4993-bfeb-53cbbbba6f08",
   "model": "string",
   "prompt": "string",
@@ -864,6 +868,8 @@
 | `credential_hint`                | string                                                                                 | false    |              |                                                                                                                                                                                                                                           |
 | `credential_kind`                | string                                                                                 | false    |              |                                                                                                                                                                                                                                           |
 | `ended_at`                       | string                                                                                 | false    |              |                                                                                                                                                                                                                                           |
+| `error_message`                  | string                                                                                 | false    |              | Error message is the raw terminal upstream error message from the root interception. Nil when the interception succeeded.                                                                                                                 |
+| `error_type`                     | string                                                                                 | false    |              | Error type is the categorized terminal upstream error from the root interception, or nil when the interception succeeded. See the aibridge_interception_error_type enum for possible values.                                              |
 | `id`                             | string                                                                                 | false    |              |                                                                                                                                                                                                                                           |
 | `model`                          | string                                                                                 | false    |              |                                                                                                                                                                                                                                           |
 | `prompt`                         | string                                                                                 | false    |              |                                                                                                                                                                                                                                           |
diff --git a/enterprise/aibridged_integration_test.go b/enterprise/aibridged_integration_test.go
index f370d8a2a6..3b66f9e36d 100644
--- a/enterprise/aibridged_integration_test.go
+++ b/enterprise/aibridged_integration_test.go
@@ -567,3 +567,93 @@ func TestIntegrationCircuitBreaker(t *testing.T) {
 	anthropicState := promtest.ToFloat64(metrics.CircuitBreakerState.WithLabelValues("anthropic", "/v1/messages", "claude-3-5-sonnet-20241022"))
 	require.Equal(t, 1.0, anthropicState, "Anthropic CircuitBreakerState should be 1 (open)")
 }
+
+// TestIntegrationRecordsUpstreamError validates that a failed interception
+// persists a categorized upstream error on its database row.
+func TestIntegrationRecordsUpstreamError(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	// Mock upstreams that reject with 401 Unauthorized.
+	unauthorizedHandler := func(body string) http.HandlerFunc {
+		return func(w http.ResponseWriter, r *http.Request) {
+			w.Header().Set("Content-Type", "application/json")
+			w.Header().Set("x-should-retry", "false")
+			w.WriteHeader(http.StatusUnauthorized)
+			_, _ = w.Write([]byte(body))
+		}
+	}
+	mockOpenAI := httptest.NewServer(unauthorizedHandler(`{"error":{"message":"Incorrect API key","type":"invalid_request_error","code":"invalid_api_key"}}`))
+	t.Cleanup(mockOpenAI.Close)
+	mockAnthropic := httptest.NewServer(unauthorizedHandler(`{"type":"error","error":{"type":"authentication_error","message":"invalid x-api-key"}}`))
+	t.Cleanup(mockAnthropic.Close)
+
+	db, ps := dbtestutil.NewDB(t)
+	client, _, api, firstUser := coderdenttest.NewWithAPI(t, &coderdenttest.Options{
+		Options: &coderdtest.Options{Database: db, Pubsub: ps},
+	})
+
+	userClient, _ := coderdtest.CreateAnotherUser(t, client, firstUser.OrganizationID)
+	apiKey, err := userClient.CreateToken(ctx, "me", codersdk.CreateTokenRequest{
+		TokenName: fmt.Sprintf("test-key-%d", time.Now().UnixNano()),
+		Lifetime:  time.Hour,
+		Scope:     codersdk.APIKeyScopeCoderAll,
+	})
+	require.NoError(t, err)
+
+	aiBridgeClient, err := api.AGPL.CreateInMemoryAIBridgeServer(ctx)
+	require.NoError(t, err)
+
+	logger := testutil.Logger(t)
+	providers := []aibridge.Provider{
+		aibridge.NewOpenAIProvider(aibridge.OpenAIConfig{BaseURL: mockOpenAI.URL, KeyPool: singleKeyPool(t, config.ProviderOpenAI, "test-key")}),
+		aibridgetest.NewAnthropicProvider(t, aibridge.AnthropicConfig{BaseURL: mockAnthropic.URL, KeyPool: singleKeyPool(t, config.ProviderAnthropic, "test-key")}, nil),
+	}
+	pool, err := aibridged.NewCachedBridgePool(aibridged.DefaultPoolOptions, providers, logger, nil, testTracer)
+	require.NoError(t, err)
+
+	srv, err := aibridged.New(ctx, pool, func(ctx context.Context) (aibridged.DRPCClient, error) {
+		return aiBridgeClient, nil
+	}, logger, testTracer)
+	require.NoError(t, err, "create new aibridged")
+	t.Cleanup(func() { _ = srv.Shutdown(ctx) })
+
+	cases := []struct {
+		name string
+		path string
+		body string
+	}{
+		{"openai_blocking", "/openai/v1/chat/completions", `{"messages":[{"role":"user","content":"test"}],"model":"gpt-4","stream":false}`},
+		{"openai_streaming", "/openai/v1/chat/completions", `{"messages":[{"role":"user","content":"test"}],"model":"gpt-4","stream":true}`},
+		{"anthropic_blocking", "/anthropic/v1/messages", `{"messages":[{"role":"user","content":"test"}],"model":"claude-3-5-sonnet-20241022","max_tokens":100,"stream":false}`},
+		{"anthropic_streaming", "/anthropic/v1/messages", `{"messages":[{"role":"user","content":"test"}],"model":"claude-3-5-sonnet-20241022","max_tokens":100,"stream":true}`},
+	}
+
+	// Requests are fired sequentially: they share the centralized key pool and
+	// database, and the aggregate assertion below depends on all of them.
+	for _, tc := range cases {
+		req, err := http.NewRequestWithContext(ctx, http.MethodPost, tc.path, bytes.NewBufferString(tc.body))
+		require.NoError(t, err)
+		req.Header.Add("Authorization", "Bearer "+apiKey.Key)
+		req.Header.Add("Accept", "application/json")
+
+		rec := httptest.NewRecorder()
+		srv.ServeHTTP(rec, req)
+		t.Logf("%s request: status=%d", tc.name, rec.Code)
+	}
+
+	// The interception rows should record the unauthorized upstream failure.
+	// Both blocking and streaming interceptors surface the centralized key-pool
+	// permanent exhaustion, which categorizes as unauthorized.
+	intcs, err := db.GetAIBridgeInterceptions(ctx)
+	require.NoError(t, err)
+	require.Len(t, intcs, len(cases))
+	for _, intc := range intcs {
+		require.True(t, intc.EndedAt.Valid, "interception %s should be ended", intc.ID)
+		require.True(t, intc.ErrorType.Valid, "interception %s should record an error type", intc.ID)
+		require.Equal(t, database.AibridgeInterceptionErrorTypeUnauthorized, intc.ErrorType.AIBridgeInterceptionErrorType)
+		require.True(t, intc.ErrorMessage.Valid, "interception %s should record an error message", intc.ID)
+		require.NotEmpty(t, intc.ErrorMessage.String)
+	}
+}
diff --git a/site/src/api/typesGenerated.ts b/site/src/api/typesGenerated.ts
index ee8d0d44b4..7095d7de7a 100644
--- a/site/src/api/typesGenerated.ts
+++ b/site/src/api/typesGenerated.ts
@@ -203,6 +203,17 @@ export interface AIBridgeThread {
 	readonly ended_at?: string;
 	readonly token_usage: AIBridgeSessionThreadsTokenUsage;
 	readonly agentic_actions: readonly AIBridgeAgenticAction[];
+	/**
+	 * ErrorType is the categorized terminal upstream error from the root
+	 * interception, or nil when the interception succeeded. See the
+	 * aibridge_interception_error_type enum for possible values.
+	 */
+	readonly error_type?: string;
+	/**
+	 * ErrorMessage is the raw terminal upstream error message from the root
+	 * interception. Nil when the interception succeeded.
+	 */
+	readonly error_message?: string;
 	/**
 	 * AgentFirewallSessionID links this thread to an agent firewall
 	 * confinement session. Nil when the request did not pass through