diff --git a/coderd/x/chatd/chatd.go b/coderd/x/chatd/chatd.go
index 8c8e20abe2..1f88828c6a 100644
--- a/coderd/x/chatd/chatd.go
+++ b/coderd/x/chatd/chatd.go
@@ -4244,6 +4244,25 @@ func shouldClearRetryPhaseForStatus(status codersdk.ChatStatus) bool {
 	}
 }
 
+func (p *Server) clearProvisionalStreamParts(chatID uuid.UUID) {
+	val, ok := p.chatStreams.Load(chatID)
+	if !ok {
+		return
+	}
+	rs, ok := val.(*chatStreamState)
+	if !ok {
+		return
+	}
+
+	// Streamed parts are provisional until a durable message commits
+	// them. A retry rolls back the failed attempt before replacement
+	// parts are streamed.
+	rs.mu.Lock()
+	rs.buffer = nil
+	rs.resetDropCounters()
+	rs.mu.Unlock()
+}
+
 func (p *Server) publishToStream(chatID uuid.UUID, event codersdk.ChatStreamEvent) {
 	state := p.getOrCreateStreamState(chatID)
 	state.mu.Lock()
@@ -7796,14 +7815,7 @@ func (p *Server) runChat(
 			classified chatretry.ClassifiedError,
 			delay time.Duration,
 		) {
-			if val, ok := p.chatStreams.Load(chat.ID); ok {
-				if rs, ok := val.(*chatStreamState); ok {
-					rs.mu.Lock()
-					rs.buffer = nil
-					rs.resetDropCounters()
-					rs.mu.Unlock()
-				}
-			}
+			p.clearProvisionalStreamParts(chat.ID)
 			logger.Warn(ctx, "retrying LLM stream",
 				slog.F("attempt", attempt),
 				slog.F("delay", delay.String()),
diff --git a/coderd/x/chatd/chatd_internal_test.go b/coderd/x/chatd/chatd_internal_test.go
index bbe63b8613..45a2940882 100644
--- a/coderd/x/chatd/chatd_internal_test.go
+++ b/coderd/x/chatd/chatd_internal_test.go
@@ -2332,6 +2332,51 @@ func TestSubscribeDoesNotReplayRetryAfterStreamResumes(t *testing.T) {
 	requireNoStreamEvent(t, events, 200*time.Millisecond)
 }
 
+func TestSubscribeDoesNotReplayFailedAttemptPartsAfterRetry(t *testing.T) {
+	t.Parallel()
+
+	ctx, cancelCtx := context.WithCancel(context.Background())
+	defer cancelCtx()
+
+	ctrl := gomock.NewController(t)
+	db := dbmock.NewMockStore(ctrl)
+
+	chatID := uuid.New()
+	chat := database.Chat{ID: chatID, Status: database.ChatStatusRunning}
+
+	gomock.InOrder(
+		db.EXPECT().GetChatByID(gomock.Any(), chatID).Return(chat, nil),
+		db.EXPECT().GetChatByID(gomock.Any(), chatID).Return(chat, nil),
+		db.EXPECT().GetChatMessagesByChatID(gomock.Any(), database.GetChatMessagesByChatIDParams{
+			ChatID:  chatID,
+			AfterID: 0,
+		}).Return(nil, nil),
+		db.EXPECT().GetChatQueuedMessages(gomock.Any(), chatID).Return(nil, nil),
+	)
+
+	server := newBufferedSubscribeTestServer(t, db, chatID)
+
+	server.publishMessagePart(chatID, codersdk.ChatMessageRoleAssistant, codersdk.ChatMessageText("failed partial"))
+	server.clearProvisionalStreamParts(chatID)
+	server.publishRetry(chatID, newTestRetryPayload())
+	server.publishMessagePart(chatID, codersdk.ChatMessageRoleAssistant, codersdk.ChatMessageText("retry recovered"))
+
+	snapshot, events, cancel, ok := server.Subscribe(ctx, chatID, nil, 0)
+	require.True(t, ok)
+	defer cancel()
+
+	requireNoSnapshotRetryEvent(t, snapshot)
+	partEvent := requireSnapshotMessagePartEvent(t, snapshot)
+	require.Equal(t, "retry recovered", partEvent.MessagePart.Part.Text)
+	for _, event := range snapshot {
+		if event.Type != codersdk.ChatStreamEventTypeMessagePart {
+			continue
+		}
+		require.NotEqual(t, "failed partial", event.MessagePart.Part.Text)
+	}
+	requireNoStreamEvent(t, events, 200*time.Millisecond)
+}
+
 func TestSubscribeDoesNotReplayRetryAfterTerminalError(t *testing.T) {
 	t.Parallel()
 
diff --git a/coderd/x/chatd/chaterror/classify.go b/coderd/x/chatd/chaterror/classify.go
index 926b058a3b..c02cf71f1b 100644
--- a/coderd/x/chatd/chaterror/classify.go
+++ b/coderd/x/chatd/chaterror/classify.go
@@ -6,6 +6,8 @@ import (
 	"strings"
 	"time"
 
+	"golang.org/x/net/http2"
+
 	"github.com/coder/coder/v2/codersdk"
 )
 
@@ -33,6 +35,10 @@ type ClassifiedError struct {
 	ChainBroken bool
 }
 
+// http2PeerResetCause mirrors golang.org/x/net/http2's unexported
+// errFromPeer message.
+const http2PeerResetCause = "received from peer"
+
 const responsesAPIDiagnosticMessage = "The chat continuation failed due to an " +
 	"internal state mismatch. This is not a configuration or billing issue."
 
@@ -188,15 +194,22 @@ func Classify(err error) ClassifiedError {
 		return classified
 	}
 
+	retryableHTTP2StreamReset, hasHTTP2StreamReset := classifyHTTP2StreamReset(err)
 	deadline := errors.Is(err, context.DeadlineExceeded) || strings.Contains(lower, "context deadline exceeded")
 	overloadedMatch := statusCode == 529 || containsAny(lower, overloadedPatterns...)
 	authStrong := statusCode == 401 || containsAny(lower, authStrongPatterns...)
 	configMatch := containsAny(lower, configPatterns...)
 	authWeak := statusCode == 403 || containsAny(lower, authWeakPatterns...)
 	rateLimitMatch := statusCode == 429 || containsAny(lower, rateLimitPatterns...)
+	timeoutPatternMatch := containsAny(lower, timeoutPatterns...)
+	if hasHTTP2StreamReset && !retryableHTTP2StreamReset {
+		// A typed HTTP/2 stream error gives us the reset code. Trust it
+		// over broader string fallbacks so protocol bugs do not retry.
+		timeoutPatternMatch = false
+	}
 	timeoutMatch := deadline || statusCode == 408 || statusCode == 502 ||
 		statusCode == 503 || statusCode == 504 ||
-		containsAny(lower, timeoutPatterns...)
+		retryableHTTP2StreamReset || timeoutPatternMatch
 	genericRetryableMatch := statusCode == 500 || containsAny(lower, genericRetryablePatterns...)
 
 	// Config signals should beat ambiguous wrapper signals so
@@ -269,6 +282,46 @@ func Classify(err error) ClassifiedError {
 	})
 }
 
+func classifyHTTP2StreamReset(err error) (retryable bool, found bool) {
+	streamErr, ok := findHTTP2StreamError(err)
+	if !ok {
+		return false, false
+	}
+	if !isPeerHTTP2StreamError(streamErr) {
+		return false, true
+	}
+	return isRetryableHTTP2StreamCode(streamErr.Code), true
+}
+
+func findHTTP2StreamError(err error) (http2.StreamError, bool) {
+	var streamErr http2.StreamError
+	if errors.As(err, &streamErr) {
+		return streamErr, true
+	}
+	var streamErrPtr *http2.StreamError
+	if errors.As(err, &streamErrPtr) && streamErrPtr != nil {
+		return *streamErrPtr, true
+	}
+	return http2.StreamError{}, false
+}
+
+func isPeerHTTP2StreamError(streamErr http2.StreamError) bool {
+	return streamErr.Cause != nil && streamErr.Cause.Error() == http2PeerResetCause
+}
+
+func isRetryableHTTP2StreamCode(code http2.ErrCode) bool {
+	switch code {
+	case http2.ErrCodeNo,
+		http2.ErrCodeInternal,
+		http2.ErrCodeRefusedStream,
+		http2.ErrCodeCancel,
+		http2.ErrCodeEnhanceYourCalm:
+		return true
+	default:
+		return false
+	}
+}
+
 func streamIncompleteClassification(
 	lowerMessage string,
 	provider string,
diff --git a/coderd/x/chatd/chaterror/classify_test.go b/coderd/x/chatd/chaterror/classify_test.go
index a599e158ae..6fd036cae5 100644
--- a/coderd/x/chatd/chaterror/classify_test.go
+++ b/coderd/x/chatd/chaterror/classify_test.go
@@ -10,6 +10,7 @@ import (
 
 	"charm.land/fantasy"
 	"github.com/stretchr/testify/require"
+	"golang.org/x/net/http2"
 	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/coderd/x/chatd/chaterror"
@@ -332,6 +333,11 @@ func TestClassify_PatternCoverage(t *testing.T) {
 		{name: "GOAWAYLiteral", err: "goaway", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
 		{name: "HTTP2StreamClosedLiteral", err: "http2: stream closed", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
 		{name: "UseOfClosedNetworkConnectionLiteral", err: "use of closed network connection", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
+		{name: "HTTP2InternalErrorReceivedFromPeerLiteral", err: "internal_error; received from peer", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
+		{name: "HTTP2RefusedStreamReceivedFromPeerLiteral", err: "refused_stream; received from peer", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
+		{name: "HTTP2CancelReceivedFromPeerLiteral", err: "cancel; received from peer", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
+		{name: "HTTP2EnhanceYourCalmReceivedFromPeerLiteral", err: "enhance_your_calm; received from peer", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
+		{name: "HTTP2NoErrorReceivedFromPeerLiteral", err: "no_error; received from peer", wantKind: codersdk.ChatErrorKindTimeout, wantRetry: true},
 		{name: "AuthenticationLiteral", err: "authentication", wantKind: codersdk.ChatErrorKindAuth, wantRetry: false},
 		{name: "UnauthorizedLiteral", err: "unauthorized", wantKind: codersdk.ChatErrorKindAuth, wantRetry: false},
 		{name: "InvalidAPIKeyLiteral", err: "invalid api key", wantKind: codersdk.ChatErrorKindAuth, wantRetry: false},
@@ -429,6 +435,10 @@ func TestClassify_HTTP2TransportErrors(t *testing.T) {
 			name: "HTTP2StreamClosed",
 			err:  "http2: stream closed",
 		},
+		{
+			name: "HTTP2PeerInternalStreamReset",
+			err:  "stream error: stream ID 455; INTERNAL_ERROR; received from peer",
+		},
 		{
 			name: "UseOfClosedNetworkConnectionOnPOST",
 			err:  `Post "https://example.com/v1/messages": use of closed network connection`,
@@ -487,6 +497,12 @@ func TestClassify_HTTP2TransportErrors(t *testing.T) {
 			provider:    "openai",
 			wantMessage: "OpenAI is temporarily unavailable.",
 		},
+		{
+			name:        "AnthropicPeerInternalStreamReset",
+			err:         `stream response: Post "https://api.anthropic.com/v1/messages": stream error: stream ID 455; INTERNAL_ERROR; received from peer`,
+			provider:    "anthropic",
+			wantMessage: "Anthropic is temporarily unavailable.",
+		},
 		{
 			name:        "GoogleGOAWAY",
 			err:         `stream response: Post "https://generativelanguage.googleapis.com/v1beta/models/gemini-pro:streamGenerateContent": http2: server sent GOAWAY and closed the connection`,
@@ -508,6 +524,208 @@ func TestClassify_HTTP2TransportErrors(t *testing.T) {
 	}
 }
 
+func TestClassify_HTTP2StreamErrorValues(t *testing.T) {
+	t.Parallel()
+
+	peerReset := func(code http2.ErrCode) http2.StreamError {
+		return http2.StreamError{
+			StreamID: 455,
+			Code:     code,
+			Cause:    xerrors.New("received from peer"),
+		}
+	}
+
+	retryable := []struct {
+		name string
+		err  error
+		want chaterror.ClassifiedError
+	}{
+		{
+			name: "Internal",
+			err:  peerReset(http2.ErrCodeInternal),
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+		{
+			name: "RefusedStream",
+			err:  peerReset(http2.ErrCodeRefusedStream),
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+		{
+			name: "CancelPointer",
+			err: &http2.StreamError{
+				StreamID: 455,
+				Code:     http2.ErrCodeCancel,
+				Cause:    xerrors.New("received from peer"),
+			},
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+		{
+			name: "EnhanceYourCalm",
+			err:  peerReset(http2.ErrCodeEnhanceYourCalm),
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+		{
+			name: "NoError",
+			err:  peerReset(http2.ErrCodeNo),
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+	}
+
+	for _, tt := range retryable {
+		t.Run("Retryable/"+tt.name, func(t *testing.T) {
+			t.Parallel()
+			require.Equal(t, tt.want, chaterror.Classify(tt.err))
+		})
+	}
+
+	localNonRetryable := []struct {
+		name string
+		err  error
+	}{
+		{
+			name: "CancelWithoutPeerCause",
+			err: http2.StreamError{
+				StreamID: 455,
+				Code:     http2.ErrCodeCancel,
+			},
+		},
+		{
+			name: "InternalWithLocalCause",
+			err: http2.StreamError{
+				StreamID: 455,
+				Code:     http2.ErrCodeInternal,
+				Cause:    xerrors.New("local transport reset"),
+			},
+		},
+	}
+	for _, tt := range localNonRetryable {
+		t.Run("NonRetryable/"+tt.name, func(t *testing.T) {
+			t.Parallel()
+			classified := chaterror.Classify(tt.err)
+			require.Equal(t, codersdk.ChatErrorKindGeneric, classified.Kind)
+			require.False(t, classified.Retryable)
+		})
+	}
+
+	nonRetryable := []struct {
+		name string
+		code http2.ErrCode
+	}{
+		{name: "Protocol", code: http2.ErrCodeProtocol},
+		{name: "FlowControl", code: http2.ErrCodeFlowControl},
+		{name: "FrameSize", code: http2.ErrCodeFrameSize},
+		{name: "Compression", code: http2.ErrCodeCompression},
+	}
+	for _, tt := range nonRetryable {
+		t.Run("NonRetryable/"+tt.name, func(t *testing.T) {
+			t.Parallel()
+			classified := chaterror.Classify(peerReset(tt.code))
+			require.Equal(t, codersdk.ChatErrorKindGeneric, classified.Kind)
+			require.False(t, classified.Retryable)
+		})
+	}
+}
+
+func TestClassify_HTTP2StreamIDDoesNotBecomeStatusCode(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name string
+		err  error
+		want chaterror.ClassifiedError
+	}{
+		{
+			name: "RetryableInternalWithAuthLikeStreamID",
+			err: http2.StreamError{
+				StreamID: 401,
+				Code:     http2.ErrCodeInternal,
+				Cause:    xerrors.New("received from peer"),
+			},
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+		{
+			name: "NonRetryableProtocolWithTimeoutLikeStreamID",
+			err: http2.StreamError{
+				StreamID: 503,
+				Code:     http2.ErrCodeProtocol,
+				Cause:    xerrors.New("received from peer"),
+			},
+			want: chaterror.ClassifiedError{
+				Message: "The chat request failed unexpectedly.",
+				Kind:    codersdk.ChatErrorKindGeneric,
+			},
+		},
+		{
+			name: "StringFallbackInternalWithAuthLikeStreamID",
+			err:  xerrors.New("stream error: stream ID 401; INTERNAL_ERROR; received from peer"),
+			want: chaterror.ClassifiedError{
+				Message:   "The AI provider is temporarily unavailable.",
+				Kind:      codersdk.ChatErrorKindTimeout,
+				Retryable: true,
+			},
+		},
+		{
+			name: "StringProtocolWithTimeoutLikeStreamID",
+			err:  xerrors.New("stream error: stream ID 503; PROTOCOL_ERROR; received from peer"),
+			want: chaterror.ClassifiedError{
+				Message: "The chat request failed unexpectedly.",
+				Kind:    codersdk.ChatErrorKindGeneric,
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+			require.Equal(t, tt.want, chaterror.Classify(tt.err))
+		})
+	}
+}
+
+func TestClassify_StatusCodeBeatsTypedHTTP2StreamError(t *testing.T) {
+	t.Parallel()
+
+	err := xerrors.Errorf(
+		"provider returned status 401: %w",
+		http2.StreamError{
+			StreamID: 455,
+			Code:     http2.ErrCodeInternal,
+			Cause:    xerrors.New("received from peer"),
+		},
+	)
+
+	require.Equal(t, chaterror.ClassifiedError{
+		Message:    "Authentication with the AI provider failed. Check the API key, permissions, and billing settings.",
+		Kind:       codersdk.ChatErrorKindAuth,
+		Retryable:  false,
+		StatusCode: 401,
+	}, chaterror.Classify(err))
+}
+
 // TestClassify_StatusCodeBeatsHTTP2Transport ensures explicit status
 // codes still win over the new HTTP/2 patterns.
 func TestClassify_StatusCodeBeatsHTTP2Transport(t *testing.T) {
diff --git a/coderd/x/chatd/chaterror/signals.go b/coderd/x/chatd/chaterror/signals.go
index 9f91e97e06..f23d86307e 100644
--- a/coderd/x/chatd/chaterror/signals.go
+++ b/coderd/x/chatd/chaterror/signals.go
@@ -48,6 +48,14 @@ var (
 		"goaway",
 		"http2: stream closed",
 		"use of closed network connection",
+		// Stringified HTTP/2 RST_STREAM errors. Classify uses
+		// typed http2.StreamError values when they survive wrapping;
+		// these patterns cover bridge layers that flatten errors.
+		"internal_error; received from peer",
+		"refused_stream; received from peer",
+		"cancel; received from peer",
+		"enhance_your_calm; received from peer",
+		"no_error; received from peer",
 	}
 	authStrongPatterns = []string{
 		"authentication",
@@ -83,9 +91,7 @@ func extractStatusCode(lower string) int {
 		return 0
 	}
 	for _, loc := range standaloneStatusPattern.FindAllStringIndex(lower, -1) {
-		// Skip values in host:port text. A later standalone status code in the
-		// same message may still be valid, so keep scanning.
-		if loc[0] > 0 && lower[loc[0]-1] == ':' {
+		if shouldSkipStandaloneStatusMatch(lower, loc[0]) {
 			continue
 		}
 		if code, err := strconv.Atoi(lower[loc[0]:loc[1]]); err == nil {
@@ -96,6 +102,21 @@ func extractStatusCode(lower string) int {
 	return 0
 }
 
+func shouldSkipStandaloneStatusMatch(lower string, start int) bool {
+	// Skip values in host:port text. A later standalone status code in the
+	// same message may still be valid, so keep scanning.
+	if start > 0 && lower[start-1] == ':' {
+		return true
+	}
+
+	// Go's HTTP/2 stream reset errors include "stream ID N". Those IDs are
+	// not HTTP status codes, even when they happen to equal 401, 429, or 503.
+	prefix := strings.TrimRight(lower[:start], " \t\r\n")
+	prefix = strings.TrimRight(prefix, ":=")
+	prefix = strings.TrimRight(prefix, " \t\r\n")
+	return strings.HasSuffix(prefix, "stream id")
+}
+
 func detectProvider(lower string) string {
 	for _, hint := range providerHints {
 		if containsAny(lower, hint.patterns...) {
diff --git a/coderd/x/chatd/chaterror/signals_test.go b/coderd/x/chatd/chaterror/signals_test.go
index 799bc1033d..4d79ded548 100644
--- a/coderd/x/chatd/chaterror/signals_test.go
+++ b/coderd/x/chatd/chaterror/signals_test.go
@@ -27,6 +27,9 @@ func TestExtractStatusCode(t *testing.T) {
 		{name: "PortNumberHostIsNotStatus", input: "proxy.internal:502 unreachable", want: 0},
 		{name: "PortNumberDialIsNotStatus", input: "dial tcp 172.16.0.5:429: refused", want: 0},
 		{name: "PortThenRealStatusReturnsRealStatus", input: "proxy at 10.0.0.1:500 returned 503", want: 503},
+		{name: "HTTP2StreamIDIsNotStatus", input: "stream error: stream ID 401; INTERNAL_ERROR; received from peer", want: 0},
+		{name: "HTTP2StreamIDWithPunctuationIsNotStatus", input: "stream error: stream ID: 503; PROTOCOL_ERROR; received from peer", want: 0},
+		{name: "HTTP2StreamIDThenExplicitStatusReturnsStatus", input: "stream error: stream ID 455; status 503 from upstream", want: 503},
 		{name: "NoFabricatedOverloadStatus", input: "anthropic overloaded_error", want: 0},
 		{name: "NoFabricatedRateLimitStatus", input: "too many requests", want: 0},
 		{name: "NoFabricatedBadGatewayStatus", input: "bad gateway", want: 0},