diff --git a/src/internal/connector/exchange/api/mail_test.go b/src/internal/connector/exchange/api/mail_test.go
index ad134041e..2ce0cd537 100644
--- a/src/internal/connector/exchange/api/mail_test.go
+++ b/src/internal/connector/exchange/api/mail_test.go
@@ -157,7 +157,7 @@ func (suite *MailAPIUnitSuite) TestMailInfo() {
 	}
 }
 
-type MailAPIE2ESuite struct {
+type MailAPIIntgSuite struct {
 	tester.Suite
 	credentials account.M365Config
 	ac          api.Client
@@ -165,9 +165,9 @@ type MailAPIE2ESuite struct {
 }
 
 // We do end up mocking the actual request, but creating the rest
-// similar to E2E suite
-func TestMailAPIE2ESuite(t *testing.T) {
-	suite.Run(t, &MailAPIE2ESuite{
+// similar to full integration tests.
+func TestMailAPIIntgSuite(t *testing.T) {
+	suite.Run(t, &MailAPIIntgSuite{
 		Suite: tester.NewIntegrationSuite(
 			t,
 			[][]string{tester.M365AcctCredEnvs},
@@ -175,7 +175,7 @@ func TestMailAPIE2ESuite(t *testing.T) {
 	})
 }
 
-func (suite *MailAPIE2ESuite) SetupSuite() {
+func (suite *MailAPIIntgSuite) SetupSuite() {
 	t := suite.T()
 
 	a := tester.NewM365Account(t)
@@ -205,7 +205,7 @@ func getJSONObject(t *testing.T, thing serialization.Parsable) map[string]interf
 	return out
 }
 
-func (suite *MailAPIE2ESuite) TestHugeAttachmentListDownload() {
+func (suite *MailAPIIntgSuite) TestHugeAttachmentListDownload() {
 	mid := "fake-message-id"
 	aid := "fake-attachment-id"
 
diff --git a/src/internal/connector/graph/errors.go b/src/internal/connector/graph/errors.go
index 9f83a1c50..527465621 100644
--- a/src/internal/connector/graph/errors.go
+++ b/src/internal/connector/graph/errors.go
@@ -43,6 +43,12 @@ const (
 	syncStateNotFound           errorCode = "SyncStateNotFound"
 )
 
+type errorMessage string
+
+const (
+	IOErrDuringRead errorMessage = "IO error during request payload read"
+)
+
 const (
 	mysiteURLNotFound = "unable to retrieve user's mysite url"
 	mysiteNotFound    = "user's mysite not found"
@@ -241,6 +247,26 @@ func Stack(ctx context.Context, e error) *clues.Err {
 	return setLabels(clues.Stack(e).WithClues(ctx).With(data...), innerMsg)
 }
 
+// stackReq is a helper function that extracts ODataError metadata from
+// the error, plus http req/resp data.  If the error is not an ODataError
+// type, returns the error with only the req/resp values.
+func stackReq(
+	ctx context.Context,
+	req *http.Request,
+	resp *http.Response,
+	e error,
+) *clues.Err {
+	if e == nil {
+		return nil
+	}
+
+	se := Stack(ctx, e).
+		WithMap(reqData(req)).
+		WithMap(respData(resp))
+
+	return se
+}
+
 // Checks for the following conditions and labels the error accordingly:
 // * mysiteNotFound | mysiteURLNotFound
 // * malware
@@ -290,6 +316,34 @@ func errData(err odataerrors.ODataErrorable) (string, []any, string) {
 	return mainMsg, data, strings.ToLower(msgConcat)
 }
 
+func reqData(req *http.Request) map[string]any {
+	if req == nil {
+		return nil
+	}
+
+	r := map[string]any{}
+	r["req_method"] = req.Method
+	r["req_len"] = req.ContentLength
+
+	if req.URL != nil {
+		r["req_url"] = LoggableURL(req.URL.String())
+	}
+
+	return r
+}
+
+func respData(resp *http.Response) map[string]any {
+	if resp == nil {
+		return nil
+	}
+
+	r := map[string]any{}
+	r["resp_status"] = resp.Status
+	r["resp_len"] = resp.ContentLength
+
+	return r
+}
+
 func appendIf(a []any, k string, v *string) []any {
 	if v == nil {
 		return a
diff --git a/src/internal/connector/graph/http_wrapper.go b/src/internal/connector/graph/http_wrapper.go
index 1410fb194..bc469c5f2 100644
--- a/src/internal/connector/graph/http_wrapper.go
+++ b/src/internal/connector/graph/http_wrapper.go
@@ -141,7 +141,7 @@ func defaultTransport() http.RoundTripper {
 
 func internalMiddleware(cc *clientConfig) []khttp.Middleware {
 	return []khttp.Middleware{
-		&RetryHandler{
+		&RetryMiddleware{
 			MaxRetries: cc.maxRetries,
 			Delay:      cc.minDelay,
 		},
diff --git a/src/internal/connector/graph/middleware.go b/src/internal/connector/graph/middleware.go
index 57825c38f..4bd914dbf 100644
--- a/src/internal/connector/graph/middleware.go
+++ b/src/internal/connector/graph/middleware.go
@@ -13,6 +13,7 @@ import (
 	"github.com/alcionai/clues"
 	backoff "github.com/cenkalti/backoff/v4"
 	khttp "github.com/microsoft/kiota-http-go"
+	"golang.org/x/exp/slices"
 	"golang.org/x/time/rate"
 
 	"github.com/alcionai/corso/src/internal/common/pii"
@@ -98,7 +99,7 @@ func LoggableURL(url string) pii.SafeURL {
 	}
 }
 
-func (handler *LoggingMiddleware) Intercept(
+func (mw *LoggingMiddleware) Intercept(
 	pipeline khttp.Pipeline,
 	middlewareIndex int,
 	req *http.Request,
@@ -173,15 +174,49 @@ func getRespDump(ctx context.Context, resp *http.Response, getBody bool) string
 // Retry & Backoff
 // ---------------------------------------------------------------------------
 
-// RetryHandler handles transient HTTP responses and retries the request given the retry options
-type RetryHandler struct {
+// RetryMiddleware handles transient HTTP responses and retries the request given the retry options
+type RetryMiddleware struct {
 	// The maximum number of times a request can be retried
 	MaxRetries int
 	// The delay in seconds between retries
 	Delay time.Duration
 }
 
-func (middleware RetryHandler) retryRequest(
+// Intercept implements the interface and evaluates whether to retry a failed request.
+func (mw RetryMiddleware) Intercept(
+	pipeline khttp.Pipeline,
+	middlewareIndex int,
+	req *http.Request,
+) (*http.Response, error) {
+	ctx := req.Context()
+
+	resp, err := pipeline.Next(req, middlewareIndex)
+	if err != nil && !IsErrTimeout(err) && !IsErrConnectionReset(err) {
+		return resp, stackReq(ctx, req, resp, err)
+	}
+
+	exponentialBackOff := backoff.NewExponentialBackOff()
+	exponentialBackOff.InitialInterval = mw.Delay
+	exponentialBackOff.Reset()
+
+	resp, err = mw.retryRequest(
+		ctx,
+		pipeline,
+		middlewareIndex,
+		req,
+		resp,
+		0,
+		0,
+		exponentialBackOff,
+		err)
+	if err != nil {
+		return nil, stackReq(ctx, req, resp, err)
+	}
+
+	return resp, nil
+}
+
+func (mw RetryMiddleware) retryRequest(
 	ctx context.Context,
 	pipeline khttp.Pipeline,
 	middlewareIndex int,
@@ -190,14 +225,23 @@ func (middleware RetryHandler) retryRequest(
 	executionCount int,
 	cumulativeDelay time.Duration,
 	exponentialBackoff *backoff.ExponentialBackOff,
-	respErr error,
+	priorErr error,
 ) (*http.Response, error) {
-	if (respErr != nil || middleware.isRetriableErrorCode(req, resp.StatusCode)) &&
-		middleware.isRetriableRequest(req) &&
-		executionCount < middleware.MaxRetries {
+	ctx = clues.Add(
+		ctx,
+		"retry_count", executionCount,
+		"prev_resp_status", resp.Status)
+
+	// only retry under certain conditions:
+	// 1, there was an error.  2, the resp and/or status code match retriable conditions.
+	// 3, the request is retriable.
+	// 4, we haven't hit our max retries already.
+	if (priorErr != nil || mw.isRetriableRespCode(ctx, resp, resp.StatusCode)) &&
+		mw.isRetriableRequest(req) &&
+		executionCount < mw.MaxRetries {
 		executionCount++
 
-		delay := middleware.getRetryDelay(req, resp, exponentialBackoff)
+		delay := mw.getRetryDelay(req, resp, exponentialBackoff)
 
 		cumulativeDelay += delay
 
@@ -209,19 +253,17 @@ func (middleware RetryHandler) retryRequest(
 		case <-ctx.Done():
 			// Don't retry if the context is marked as done, it will just error out
 			// when we attempt to send the retry anyway.
-			return resp, ctx.Err()
+			return resp, clues.Stack(ctx.Err()).WithClues(ctx)
 
-		// Will exit switch-block so the remainder of the code doesn't need to be
-		// indented.
 		case <-timer.C:
 		}
 
 		response, err := pipeline.Next(req, middlewareIndex)
 		if err != nil && !IsErrTimeout(err) && !IsErrConnectionReset(err) {
-			return response, Stack(ctx, err).With("retry_count", executionCount)
+			return response, stackReq(ctx, req, response, err)
 		}
 
-		return middleware.retryRequest(ctx,
+		return mw.retryRequest(ctx,
 			pipeline,
 			middlewareIndex,
 			req,
@@ -232,18 +274,33 @@ func (middleware RetryHandler) retryRequest(
 			err)
 	}
 
-	if respErr != nil {
-		return nil, Stack(ctx, respErr).With("retry_count", executionCount)
+	if priorErr != nil {
+		return nil, stackReq(ctx, req, nil, priorErr)
 	}
 
 	return resp, nil
 }
 
-func (middleware RetryHandler) isRetriableErrorCode(req *http.Request, code int) bool {
-	return code == http.StatusInternalServerError || code == http.StatusServiceUnavailable
+var retryableRespCodes = []int{
+	http.StatusInternalServerError,
+	http.StatusServiceUnavailable,
+	http.StatusBadGateway,
+	http.StatusGatewayTimeout,
 }
 
-func (middleware RetryHandler) isRetriableRequest(req *http.Request) bool {
+func (mw RetryMiddleware) isRetriableRespCode(ctx context.Context, resp *http.Response, code int) bool {
+	if slices.Contains(retryableRespCodes, code) {
+		return true
+	}
+
+	// not a status code, but the message itself might indicate a connectivity issue that
+	// can be retried independent of the status code.
+	return strings.Contains(
+		strings.ToLower(getRespDump(ctx, resp, true)),
+		strings.ToLower(string(IOErrDuringRead)))
+}
+
+func (mw RetryMiddleware) isRetriableRequest(req *http.Request) bool {
 	isBodiedMethod := req.Method == "POST" || req.Method == "PUT" || req.Method == "PATCH"
 	if isBodiedMethod && req.Body != nil {
 		return req.ContentLength != -1
@@ -252,7 +309,7 @@ func (middleware RetryHandler) isRetriableRequest(req *http.Request) bool {
 	return true
 }
 
-func (middleware RetryHandler) getRetryDelay(
+func (mw RetryMiddleware) getRetryDelay(
 	req *http.Request,
 	resp *http.Response,
 	exponentialBackoff *backoff.ExponentialBackOff,
@@ -272,40 +329,6 @@ func (middleware RetryHandler) getRetryDelay(
 	return exponentialBackoff.NextBackOff()
 }
 
-// Intercept implements the interface and evaluates whether to retry a failed request.
-func (middleware RetryHandler) Intercept(
-	pipeline khttp.Pipeline,
-	middlewareIndex int,
-	req *http.Request,
-) (*http.Response, error) {
-	ctx := req.Context()
-
-	response, err := pipeline.Next(req, middlewareIndex)
-	if err != nil && !IsErrTimeout(err) {
-		return response, Stack(ctx, err)
-	}
-
-	exponentialBackOff := backoff.NewExponentialBackOff()
-	exponentialBackOff.InitialInterval = middleware.Delay
-	exponentialBackOff.Reset()
-
-	response, err = middleware.retryRequest(
-		ctx,
-		pipeline,
-		middlewareIndex,
-		req,
-		response,
-		0,
-		0,
-		exponentialBackOff,
-		err)
-	if err != nil {
-		return nil, Stack(ctx, err)
-	}
-
-	return response, nil
-}
-
 // We're trying to keep calls below the 10k-per-10-minute threshold.
 // 15 tokens every second nets 900 per minute.  That's 9000 every 10 minutes,
 // which is a bit below the mark.
@@ -341,7 +364,7 @@ func QueueRequest(ctx context.Context) {
 // request limits.
 type ThrottleControlMiddleware struct{}
 
-func (handler *ThrottleControlMiddleware) Intercept(
+func (mw *ThrottleControlMiddleware) Intercept(
 	pipeline khttp.Pipeline,
 	middlewareIndex int,
 	req *http.Request,
@@ -353,7 +376,7 @@ func (handler *ThrottleControlMiddleware) Intercept(
 // MetricsMiddleware aggregates per-request metrics on the events bus
 type MetricsMiddleware struct{}
 
-func (handler *MetricsMiddleware) Intercept(
+func (mw *MetricsMiddleware) Intercept(
 	pipeline khttp.Pipeline,
 	middlewareIndex int,
 	req *http.Request,
diff --git a/src/internal/connector/graph/middleware_test.go b/src/internal/connector/graph/middleware_test.go
new file mode 100644
index 000000000..3a8ec7656
--- /dev/null
+++ b/src/internal/connector/graph/middleware_test.go
@@ -0,0 +1,152 @@
+package graph
+
+import (
+	"net/http"
+	"testing"
+	"time"
+
+	"github.com/alcionai/clues"
+	khttp "github.com/microsoft/kiota-http-go"
+	msgraphsdkgo "github.com/microsoftgraph/msgraph-sdk-go"
+	msgraphgocore "github.com/microsoftgraph/msgraph-sdk-go-core"
+	"github.com/microsoftgraph/msgraph-sdk-go/users"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"github.com/stretchr/testify/suite"
+
+	"github.com/alcionai/corso/src/internal/tester"
+	"github.com/alcionai/corso/src/pkg/account"
+)
+
+func newBodylessTestMW(onIntercept func(), code int, err error) testMW {
+	return testMW{
+		err:         err,
+		onIntercept: onIntercept,
+		resp:        &http.Response{StatusCode: code},
+	}
+}
+
+type testMW struct {
+	err         error
+	onIntercept func()
+	resp        *http.Response
+}
+
+func (mw testMW) Intercept(
+	pipeline khttp.Pipeline,
+	middlewareIndex int,
+	req *http.Request,
+) (*http.Response, error) {
+	mw.onIntercept()
+	return mw.resp, mw.err
+}
+
+// can't use graph/mock.CreateAdapter() due to circular references.
+func mockAdapter(creds account.M365Config, mw khttp.Middleware) (*msgraphsdkgo.GraphRequestAdapter, error) {
+	auth, err := GetAuth(
+		creds.AzureTenantID,
+		creds.AzureClientID,
+		creds.AzureClientSecret)
+	if err != nil {
+		return nil, err
+	}
+
+	var (
+		clientOptions = msgraphsdkgo.GetDefaultClientOptions()
+		cc            = populateConfig(MinimumBackoff(10 * time.Millisecond))
+		middlewares   = append(kiotaMiddlewares(&clientOptions, cc), mw)
+		httpClient    = msgraphgocore.GetDefaultClient(&clientOptions, middlewares...)
+	)
+
+	httpClient.Timeout = 5 * time.Second
+
+	cc.apply(httpClient)
+
+	return msgraphsdkgo.NewGraphRequestAdapterWithParseNodeFactoryAndSerializationWriterFactoryAndHttpClient(
+		auth,
+		nil, nil,
+		httpClient)
+}
+
+type RetryMWIntgSuite struct {
+	tester.Suite
+	creds account.M365Config
+}
+
+// We do end up mocking the actual request, but creating the rest
+// similar to E2E suite
+func TestRetryMWIntgSuite(t *testing.T) {
+	suite.Run(t, &RetryMWIntgSuite{
+		Suite: tester.NewIntegrationSuite(
+			t,
+			[][]string{tester.M365AcctCredEnvs}),
+	})
+}
+
+func (suite *RetryMWIntgSuite) SetupSuite() {
+	var (
+		a   = tester.NewM365Account(suite.T())
+		err error
+	)
+
+	suite.creds, err = a.M365Config()
+	require.NoError(suite.T(), err, clues.ToCore(err))
+}
+
+func (suite *RetryMWIntgSuite) TestRetryMiddleware_Intercept_byStatusCode() {
+	var (
+		uri  = "https://graph.microsoft.com"
+		path = "/v1.0/users/user/messages/foo"
+		url  = uri + path
+	)
+
+	tests := []struct {
+		name             string
+		status           int
+		expectRetryCount int
+		mw               testMW
+		expectErr        assert.ErrorAssertionFunc
+	}{
+		{
+			name:             "200, no retries",
+			status:           http.StatusOK,
+			expectRetryCount: 0,
+			expectErr:        assert.NoError,
+		},
+		{
+			name:             "400, no retries",
+			status:           http.StatusBadRequest,
+			expectRetryCount: 0,
+			expectErr:        assert.Error,
+		},
+		{
+			// don't test 504: gets intercepted by graph client for long waits.
+			name:             "502",
+			status:           http.StatusBadGateway,
+			expectRetryCount: defaultMaxRetries,
+			expectErr:        assert.Error,
+		},
+	}
+
+	for _, test := range tests {
+		suite.Run(test.name, func() {
+			ctx, flush := tester.NewContext()
+			defer flush()
+
+			t := suite.T()
+			called := 0
+			mw := newBodylessTestMW(func() { called++ }, test.status, nil)
+
+			adpt, err := mockAdapter(suite.creds, mw)
+			require.NoError(t, err, clues.ToCore(err))
+
+			// url doesn't fit the builder, but that shouldn't matter
+			_, err = users.NewCountRequestBuilder(url, adpt).Get(ctx, nil)
+			test.expectErr(t, err, clues.ToCore(err))
+
+			// -1 because the non-retried call always counts for one, then
+			// we increment based on the number of retry attempts.
+			assert.Equal(t, test.expectRetryCount, called-1)
+		})
+	}
+}
diff --git a/src/internal/connector/graph/service.go b/src/internal/connector/graph/service.go
index 42ef4440c..9db7fb825 100644
--- a/src/internal/connector/graph/service.go
+++ b/src/internal/connector/graph/service.go
@@ -243,7 +243,7 @@ func kiotaMiddlewares(
 
 	mw = append(mw, []khttp.Middleware{
 		msgraphgocore.NewGraphTelemetryHandler(options),
-		&RetryHandler{
+		&RetryMiddleware{
 			MaxRetries: cc.maxRetries,
 			Delay:      cc.minDelay,
 		},