diff --git a/src/go.mod b/src/go.mod
index dce43535b..31283977b 100644
--- a/src/go.mod
+++ b/src/go.mod
@@ -7,6 +7,7 @@ require (
 	github.com/alcionai/clues v0.0.0-20230202001016-cbda58c9de9e
 	github.com/aws/aws-sdk-go v1.44.200
 	github.com/aws/aws-xray-sdk-go v1.8.0
+	github.com/cenkalti/backoff/v4 v4.2.0
 	github.com/google/uuid v1.3.0
 	github.com/hashicorp/go-multierror v1.1.1
 	github.com/kopia/kopia v0.12.2-0.20230123092305-e5387cec0acb
diff --git a/src/go.sum b/src/go.sum
index e76eeca18..a3abe62e8 100644
--- a/src/go.sum
+++ b/src/go.sum
@@ -73,6 +73,8 @@ github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
 github.com/beorn7/perks v1.0.1/go.mod h1:G2ZrVWU2WbWT9wwq4/hrbKbnv/1ERSJQ0ibhJ6rlkpw=
 github.com/bmizerany/assert v0.0.0-20160611221934-b7ed37b82869 h1:DDGfHa7BWjL4YnC6+E63dPcxHo2sUxDIu8g3QgEJdRY=
 github.com/bmizerany/assert v0.0.0-20160611221934-b7ed37b82869/go.mod h1:Ekp36dRnpXw/yCqJaO+ZrUyxD+3VXMFFr56k5XYrpB4=
+github.com/cenkalti/backoff/v4 v4.2.0 h1:HN5dHm3WBOgndBH6E8V0q2jIYIR3s9yglV8k/+MN3u4=
+github.com/cenkalti/backoff/v4 v4.2.0/go.mod h1:Y3VNntkOUPxTVeUxJ/G5vcM//AlwfmyYozVcomhLiZE=
 github.com/census-instrumentation/opencensus-proto v0.2.1/go.mod h1:f6KPmirojxKA12rnyqOA5BBL4O983OfeGPqjHWSTneU=
 github.com/cespare/xxhash/v2 v2.1.1/go.mod h1:VGX0DQ3Q6kWi7AoAeZDth3/j3BFtOZR5XLFGgcrjCOs=
 github.com/cespare/xxhash/v2 v2.1.2 h1:YRXhKfTDauu4ajMg1TPgFO5jnlC2HCbmLXMcTG5cbYE=
diff --git a/src/internal/connector/discovery/api/users.go b/src/internal/connector/discovery/api/users.go
index f59737168..78962a7d2 100644
--- a/src/internal/connector/discovery/api/users.go
+++ b/src/internal/connector/discovery/api/users.go
@@ -94,10 +94,7 @@ func (c Users) GetAll(ctx context.Context, errs *fault.Errors) ([]models.Userabl
 
 	var resp models.UserCollectionResponseable
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = service.Client().Users().Get(ctx, userOptions(&userFilterNoGuests))
-		return err
-	})
+	resp, err = service.Client().Users().Get(ctx, userOptions(&userFilterNoGuests))
 
 	if err != nil {
 		return nil, clues.Wrap(err, "getting all users").WithClues(ctx).WithAll(graph.ErrData(err)...)
@@ -141,10 +138,7 @@ func (c Users) GetByID(ctx context.Context, userID string) (models.Userable, err
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = c.stable.Client().UsersById(userID).Get(ctx, nil)
-		return err
-	})
+	resp, err = c.stable.Client().UsersById(userID).Get(ctx, nil)
 
 	if err != nil {
 		return nil, clues.Wrap(err, "getting user").WithClues(ctx).WithAll(graph.ErrData(err)...)
@@ -162,10 +156,7 @@ func (c Users) GetInfo(ctx context.Context, userID string) (*UserInfo, error) {
 	)
 
 	// TODO: OneDrive
-	err = graph.RunWithRetry(func() error {
-		_, err = c.stable.Client().UsersById(userID).MailFolders().Get(ctx, nil)
-		return err
-	})
+	_, err = c.stable.Client().UsersById(userID).MailFolders().Get(ctx, nil)
 
 	if err != nil {
 		if !graph.IsErrExchangeMailFolderNotFound(err) {
diff --git a/src/internal/connector/exchange/api/contacts.go b/src/internal/connector/exchange/api/contacts.go
index 78db13c08..5de33e916 100644
--- a/src/internal/connector/exchange/api/contacts.go
+++ b/src/internal/connector/exchange/api/contacts.go
@@ -68,11 +68,7 @@ func (c Contacts) GetItem(
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		cont, err = c.stable.Client().UsersById(user).ContactsById(itemID).Get(ctx, nil)
-		return err
-	})
-
+	cont, err = c.stable.Client().UsersById(user).ContactsById(itemID).Get(ctx, nil)
 	if err != nil {
 		return nil, nil, err
 	}
@@ -91,10 +87,7 @@ func (c Contacts) GetContainerByID(
 
 	var resp models.ContactFolderable
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = c.stable.Client().UsersById(userID).ContactFoldersById(dirID).Get(ctx, ofcf)
-		return err
-	})
+	resp, err = c.stable.Client().UsersById(userID).ContactFoldersById(dirID).Get(ctx, ofcf)
 
 	return resp, err
 }
@@ -132,11 +125,7 @@ func (c Contacts) EnumerateContainers(
 		ChildFolders()
 
 	for {
-		err = graph.RunWithRetry(func() error {
-			resp, err = builder.Get(ctx, ofcf)
-			return err
-		})
-
+		resp, err = builder.Get(ctx, ofcf)
 		if err != nil {
 			return errors.Wrap(err, support.ConnectorStackErrorTrace(err))
 		}
@@ -182,10 +171,7 @@ func (p *contactPager) getPage(ctx context.Context) (api.DeltaPageLinker, error)
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = p.builder.Get(ctx, p.options)
-		return err
-	})
+	resp, err = p.builder.Get(ctx, p.options)
 
 	return resp, err
 }
diff --git a/src/internal/connector/exchange/api/events.go b/src/internal/connector/exchange/api/events.go
index cc719f7fc..a998203b8 100644
--- a/src/internal/connector/exchange/api/events.go
+++ b/src/internal/connector/exchange/api/events.go
@@ -78,10 +78,7 @@ func (c Events) GetContainerByID(
 
 	var cal models.Calendarable
 
-	err = graph.RunWithRetry(func() error {
-		cal, err = service.Client().UsersById(userID).CalendarsById(containerID).Get(ctx, ofc)
-		return err
-	})
+	cal, err = service.Client().UsersById(userID).CalendarsById(containerID).Get(ctx, ofc)
 
 	if err != nil {
 		return nil, err
@@ -100,11 +97,7 @@ func (c Events) GetItem(
 		err   error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		event, err = c.stable.Client().UsersById(user).EventsById(itemID).Get(ctx, nil)
-		return err
-	})
-
+	event, err = c.stable.Client().UsersById(user).EventsById(itemID).Get(ctx, nil)
 	if err != nil {
 		return nil, nil, err
 	}
@@ -175,11 +168,7 @@ func (c Events) EnumerateContainers(
 	for {
 		var err error
 
-		err = graph.RunWithRetry(func() error {
-			resp, err = builder.Get(ctx, ofc)
-			return err
-		})
-
+		resp, err = builder.Get(ctx, ofc)
 		if err != nil {
 			return errors.Wrap(err, support.ConnectorStackErrorTrace(err))
 		}
@@ -233,10 +222,7 @@ func (p *eventPager) getPage(ctx context.Context) (api.DeltaPageLinker, error) {
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = p.builder.Get(ctx, p.options)
-		return err
-	})
+	resp, err = p.builder.Get(ctx, p.options)
 
 	return resp, err
 }
diff --git a/src/internal/connector/exchange/api/mail.go b/src/internal/connector/exchange/api/mail.go
index f94ea0fca..443b7d3e1 100644
--- a/src/internal/connector/exchange/api/mail.go
+++ b/src/internal/connector/exchange/api/mail.go
@@ -99,10 +99,7 @@ func (c Mail) GetContainerByID(
 
 	var resp graph.Container
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = service.Client().UsersById(userID).MailFoldersById(dirID).Get(ctx, ofmf)
-		return err
-	})
+	resp, err = service.Client().UsersById(userID).MailFoldersById(dirID).Get(ctx, ofmf)
 
 	return resp, err
 }
@@ -118,11 +115,7 @@ func (c Mail) GetItem(
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		mail, err = c.stable.Client().UsersById(user).MessagesById(itemID).Get(ctx, nil)
-		return err
-	})
-
+	mail, err = c.stable.Client().UsersById(user).MessagesById(itemID).Get(ctx, nil)
 	if err != nil {
 		return nil, nil, err
 	}
@@ -188,11 +181,7 @@ func (c Mail) EnumerateContainers(
 	for {
 		var err error
 
-		err = graph.RunWithRetry(func() error {
-			resp, err = builder.Get(ctx, nil)
-			return err
-		})
-
+		resp, err = builder.Get(ctx, nil)
 		if err != nil {
 			return errors.Wrap(err, support.ConnectorStackErrorTrace(err))
 		}
@@ -234,10 +223,7 @@ func (p *mailPager) getPage(ctx context.Context) (api.DeltaPageLinker, error) {
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		page, err = p.builder.Get(ctx, p.options)
-		return err
-	})
+	page, err = p.builder.Get(ctx, p.options)
 
 	return page, err
 }
diff --git a/src/internal/connector/graph/errors.go b/src/internal/connector/graph/errors.go
index 4ac9b3ed5..b8399da4c 100644
--- a/src/internal/connector/graph/errors.go
+++ b/src/internal/connector/graph/errors.go
@@ -3,6 +3,7 @@ package graph
 import (
 	"context"
 	"fmt"
+	"net/http"
 	"net/url"
 	"os"
 
@@ -96,7 +97,7 @@ func IsErrTimeout(err error) bool {
 		return true
 	}
 
-	if errors.Is(err, context.DeadlineExceeded) || os.IsTimeout(err) {
+	if errors.Is(err, context.DeadlineExceeded) || os.IsTimeout(err) || errors.Is(err, http.ErrHandlerTimeout) {
 		return true
 	}
 
diff --git a/src/internal/connector/graph/retry_middleware.go b/src/internal/connector/graph/retry_middleware.go
new file mode 100644
index 000000000..1d66a2e81
--- /dev/null
+++ b/src/internal/connector/graph/retry_middleware.go
@@ -0,0 +1,101 @@
+package graph
+
+import (
+	"context"
+	"net/http"
+	"strconv"
+	"time"
+
+	"github.com/alcionai/corso/src/internal/connector/support"
+	backoff "github.com/cenkalti/backoff/v4"
+	khttp "github.com/microsoft/kiota-http-go"
+)
+
+// ---------------------------------------------------------------------------
+// Client Middleware
+// ---------------------------------------------------------------------------
+
+// RetryHandler handles transient HTTP responses and retries the request given the retry options
+type RetryHandler 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(
+	ctx context.Context,
+	pipeline khttp.Pipeline,
+	middlewareIndex int,
+	req *http.Request,
+	resp *http.Response,
+	executionCount int,
+	cumulativeDelay time.Duration,
+	exponentialBackoff *backoff.ExponentialBackOff,
+	respErr error,
+) (*http.Response, error) {
+	if (respErr != nil || middleware.isRetriableErrorCode(req, resp.StatusCode)) &&
+		middleware.isRetriableRequest(req) &&
+		executionCount < middleware.MaxRetries &&
+		cumulativeDelay < time.Duration(absoluteMaxDelaySeconds)*time.Second {
+		executionCount++
+
+		delay := middleware.getRetryDelay(req, resp, exponentialBackoff)
+
+		cumulativeDelay += delay
+
+		req.Header.Set(retryAttemptHeader, strconv.Itoa(executionCount))
+
+		time.Sleep(delay)
+
+		response, err := pipeline.Next(req, middlewareIndex)
+		if err != nil && !IsErrTimeout(err) {
+			return response, support.ConnectorStackErrorTraceWrap(err, "maximum retries or unretryable")
+		}
+
+		return middleware.retryRequest(ctx,
+			pipeline,
+			middlewareIndex,
+			req,
+			response,
+			executionCount,
+			cumulativeDelay,
+			exponentialBackoff,
+			err)
+	}
+
+	return resp, support.ConnectorStackErrorTraceWrap(respErr, "maximum retries or unretryable")
+}
+
+func (middleware RetryHandler) isRetriableErrorCode(req *http.Request, code int) bool {
+	return code == http.StatusInternalServerError
+}
+
+func (middleware RetryHandler) isRetriableRequest(req *http.Request) bool {
+	isBodiedMethod := req.Method == "POST" || req.Method == "PUT" || req.Method == "PATCH"
+	if isBodiedMethod && req.Body != nil {
+		return req.ContentLength != -1
+	}
+
+	return true
+}
+
+func (middleware RetryHandler) getRetryDelay(
+	req *http.Request,
+	resp *http.Response,
+	exponentialBackoff *backoff.ExponentialBackOff,
+) time.Duration {
+	var retryAfter string
+	if resp != nil {
+		retryAfter = resp.Header.Get(retryAfterHeader)
+	}
+
+	if retryAfter != "" {
+		retryAfterDelay, err := strconv.ParseFloat(retryAfter, 64)
+		if err == nil {
+			return time.Duration(retryAfterDelay) * time.Second
+		}
+	} // TODO parse the header if it's a date
+
+	return exponentialBackoff.NextBackOff()
+}
diff --git a/src/internal/connector/graph/service.go b/src/internal/connector/graph/service.go
index 992010c1a..3d2cacef9 100644
--- a/src/internal/connector/graph/service.go
+++ b/src/internal/connector/graph/service.go
@@ -7,6 +7,7 @@ import (
 	"time"
 
 	"github.com/Azure/azure-sdk-for-go/sdk/azidentity"
+	backoff "github.com/cenkalti/backoff/v4"
 	"github.com/microsoft/kiota-abstractions-go/serialization"
 	ka "github.com/microsoft/kiota-authentication-azure-go"
 	khttp "github.com/microsoft/kiota-http-go"
@@ -21,8 +22,13 @@ import (
 )
 
 const (
-	logGraphRequestsEnvKey = "LOG_GRAPH_REQUESTS"
-	numberOfRetries        = 3
+	logGraphRequestsEnvKey  = "LOG_GRAPH_REQUESTS"
+	numberOfRetries         = 3
+	retryAttemptHeader      = "Retry-Attempt"
+	retryAfterHeader        = "Retry-After"
+	defaultMaxRetries       = 3
+	defaultDelay            = 3 * time.Second
+	absoluteMaxDelaySeconds = 180
 )
 
 // AllMetadataFileNames produces the standard set of filenames used to store graph
@@ -85,6 +91,11 @@ func (s Service) Serialize(object serialization.Parsable) ([]byte, error) {
 
 type clientConfig struct {
 	noTimeout bool
+	// MaxRetries before failure
+	maxRetries int
+	// The minimum delay in seconds between retries
+	minDelay           time.Duration
+	overrideRetryCount bool
 }
 
 type option func(*clientConfig)
@@ -98,6 +109,21 @@ func (c *clientConfig) populate(opts ...option) *clientConfig {
 	return c
 }
 
+// apply updates the http.Client with the expected options.
+func (c *clientConfig) applyMiddlewareConfig() (retry int, delay time.Duration) {
+	retry = defaultMaxRetries
+	if c.overrideRetryCount {
+		retry = c.maxRetries
+	}
+
+	delay = defaultDelay
+	if c.minDelay > 0 {
+		delay = c.minDelay
+	}
+
+	return
+}
+
 // apply updates the http.Client with the expected options.
 func (c *clientConfig) apply(hc *http.Client) {
 	if c.noTimeout {
@@ -115,6 +141,19 @@ func NoTimeout() option {
 	}
 }
 
+func MaxRetries(max int) option {
+	return func(c *clientConfig) {
+		c.overrideRetryCount = true
+		c.maxRetries = max
+	}
+}
+
+func MinimumBackoff(dur time.Duration) option {
+	return func(c *clientConfig) {
+		c.minDelay = dur
+	}
+}
+
 // CreateAdapter uses provided credentials to log into M365 using Kiota Azure Library
 // with Azure identity package. An adapter object is a necessary to component
 // to create  *msgraphsdk.GraphServiceClient
@@ -147,18 +186,51 @@ func CreateAdapter(tenant, client, secret string, opts ...option) (*msgraphsdk.G
 // can utilize it on a per-download basis.
 func HTTPClient(opts ...option) *http.Client {
 	clientOptions := msgraphsdk.GetDefaultClientOptions()
-	middlewares := msgraphgocore.GetDefaultMiddlewaresWithOptions(&clientOptions)
-	middlewares = append(middlewares, &LoggingMiddleware{})
+	clientconfig := (&clientConfig{}).populate(opts...)
+	noOfRetries, minRetryDelay := clientconfig.applyMiddlewareConfig()
+	middlewares := GetKiotaMiddlewares(&clientOptions, noOfRetries, minRetryDelay)
 	httpClient := msgraphgocore.GetDefaultClient(&clientOptions, middlewares...)
 	httpClient.Timeout = time.Minute * 3
 
-	(&clientConfig{}).
-		populate(opts...).
-		apply(httpClient)
+	clientconfig.apply(httpClient)
 
 	return httpClient
 }
 
+// GetDefaultMiddlewares creates a new default set of middlewares for the Kiota request adapter
+func GetMiddlewares(maxRetry int, delay time.Duration) []khttp.Middleware {
+	return []khttp.Middleware{
+		&RetryHandler{
+			// The maximum number of times a request can be retried
+			MaxRetries: maxRetry,
+			// The delay in seconds between retries
+			Delay: delay,
+		},
+		khttp.NewRetryHandler(),
+		khttp.NewRedirectHandler(),
+		khttp.NewCompressionHandler(),
+		khttp.NewParametersNameDecodingHandler(),
+		khttp.NewUserAgentHandler(),
+		&LoggingMiddleware{},
+	}
+}
+
+// GetKiotaMiddlewares creates a default slice of middleware for the Graph Client.
+func GetKiotaMiddlewares(options *msgraphgocore.GraphClientOptions,
+	maxRetry int, minDelay time.Duration,
+) []khttp.Middleware {
+	kiotaMiddlewares := GetMiddlewares(maxRetry, minDelay)
+	graphMiddlewares := []khttp.Middleware{
+		msgraphgocore.NewGraphTelemetryHandler(options),
+	}
+	graphMiddlewaresLen := len(graphMiddlewares)
+	resultMiddlewares := make([]khttp.Middleware, len(kiotaMiddlewares)+graphMiddlewaresLen)
+	copy(resultMiddlewares, graphMiddlewares)
+	copy(resultMiddlewares[graphMiddlewaresLen:], kiotaMiddlewares)
+
+	return resultMiddlewares
+}
+
 // ---------------------------------------------------------------------------
 // Interfaces
 // ---------------------------------------------------------------------------
@@ -245,25 +317,31 @@ func (handler *LoggingMiddleware) Intercept(
 	return resp, err
 }
 
-// Run a function with retries
-func RunWithRetry(run func() error) error {
-	var err error
+// 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()
 
-	for i := 0; i < numberOfRetries; i++ {
-		err = run()
-		if err == nil {
-			return nil
-		}
-
-		// only retry on timeouts and 500-internal-errors.
-		if !(IsErrTimeout(err) || IsInternalServerError(err)) {
-			break
-		}
-
-		if i < numberOfRetries {
-			time.Sleep(time.Duration(3*(i+2)) * time.Second)
-		}
+	response, err := pipeline.Next(req, middlewareIndex)
+	if err != nil && !IsErrTimeout(err) {
+		return response, support.ConnectorStackErrorTraceWrap(err, "maximum retries or unretryable")
 	}
 
-	return support.ConnectorStackErrorTraceWrap(err, "maximum retries or unretryable")
+	exponentialBackOff := backoff.NewExponentialBackOff()
+	exponentialBackOff.InitialInterval = middleware.Delay
+	exponentialBackOff.Reset()
+
+	return middleware.retryRequest(
+		ctx,
+		pipeline,
+		middlewareIndex,
+		req,
+		response,
+		0,
+		0,
+		exponentialBackOff,
+		err)
 }
diff --git a/src/internal/connector/onedrive/api/drive.go b/src/internal/connector/onedrive/api/drive.go
index 391ea2632..6bb497307 100644
--- a/src/internal/connector/onedrive/api/drive.go
+++ b/src/internal/connector/onedrive/api/drive.go
@@ -68,10 +68,7 @@ func (p *driveItemPager) GetPage(ctx context.Context) (api.DeltaPageLinker, erro
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = p.builder.Get(ctx, p.options)
-		return err
-	})
+	resp, err = p.builder.Get(ctx, p.options)
 
 	return resp, err
 }
@@ -120,10 +117,7 @@ func (p *userDrivePager) GetPage(ctx context.Context) (api.PageLinker, error) {
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = p.builder.Get(ctx, p.options)
-		return err
-	})
+	resp, err = p.builder.Get(ctx, p.options)
 
 	return resp, err
 }
@@ -168,10 +162,7 @@ func (p *siteDrivePager) GetPage(ctx context.Context) (api.PageLinker, error) {
 		err  error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		resp, err = p.builder.Get(ctx, p.options)
-		return err
-	})
+	resp, err = p.builder.Get(ctx, p.options)
 
 	return resp, err
 }
diff --git a/src/internal/connector/onedrive/collection.go b/src/internal/connector/onedrive/collection.go
index 59494856b..08efa9994 100644
--- a/src/internal/connector/onedrive/collection.go
+++ b/src/internal/connector/onedrive/collection.go
@@ -32,10 +32,6 @@ const (
 	// TODO: Tune this later along with collectionChannelBufferSize
 	urlPrefetchChannelBufferSize = 5
 
-	// Max number of retries to get doc from M365
-	// Seems to timeout at times because of multiple requests
-	maxRetries = 4 // 1 + 3 retries
-
 	MetaFileSuffix    = ".meta"
 	DirMetaFileSuffix = ".dirmeta"
 	DataFileSuffix    = ".data"
@@ -295,10 +291,7 @@ func (oc *Collection) populateItems(ctx context.Context) {
 					itemMeta = io.NopCloser(strings.NewReader("{}"))
 					itemMetaSize = 2
 				} else {
-					err = graph.RunWithRetry(func() error {
-						itemMeta, itemMetaSize, err = oc.itemMetaReader(ctx, oc.service, oc.driveID, item)
-						return err
-					})
+					itemMeta, itemMetaSize, err = oc.itemMetaReader(ctx, oc.service, oc.driveID, item)
 
 					if err != nil {
 						errUpdater(*item.GetId(), errors.Wrap(err, "failed to get item permissions"))
@@ -333,38 +326,18 @@ func (oc *Collection) populateItems(ctx context.Context) {
 						err      error
 					)
 
-					for i := 1; i <= maxRetries; i++ {
-						_, itemData, err = oc.itemReader(oc.itemClient, item)
-						if err == nil {
-							break
-						}
-
-						if graph.IsErrUnauthorized(err) {
-							// assume unauthorized requests are a sign of an expired
-							// jwt token, and that we've overrun the available window
-							// to download the actual file.  Re-downloading the item
-							// will refresh that download url.
-							di, diErr := getDriveItem(ctx, oc.service, oc.driveID, itemID)
-							if diErr != nil {
-								err = errors.Wrap(diErr, "retrieving expired item")
-								break
-							}
-
-							item = di
-
-							continue
-
-						} else if !graph.IsErrTimeout(err) &&
-							!graph.IsInternalServerError(err) {
-							// Don't retry for non-timeout, on-unauth, as
-							// we are already retrying it in the default
-							// retry middleware
-							break
-						}
-
-						if i < maxRetries {
-							time.Sleep(1 * time.Second)
+					_, itemData, err = oc.itemReader(oc.itemClient, item)
+
+					if err != nil && graph.IsErrUnauthorized(err) {
+						// assume unauthorized requests are a sign of an expired
+						// jwt token, and that we've overrun the available window
+						// to download the actual file.  Re-downloading the item
+						// will refresh that download url.
+						di, diErr := getDriveItem(ctx, oc.service, oc.driveID, itemID)
+						if diErr != nil {
+							err = errors.Wrap(diErr, "retrieving expired item")
 						}
+						item = di
 					}
 
 					// check for errors following retries
diff --git a/src/internal/connector/onedrive/drive.go b/src/internal/connector/onedrive/drive.go
index 0418262ae..174286e64 100644
--- a/src/internal/connector/onedrive/drive.go
+++ b/src/internal/connector/onedrive/drive.go
@@ -26,13 +26,15 @@ const (
 
 	// nextLinkKey is used to find the next link in a paged
 	// graph response
-	nextLinkKey             = "@odata.nextLink"
-	itemChildrenRawURLFmt   = "https://graph.microsoft.com/v1.0/drives/%s/items/%s/children"
-	itemByPathRawURLFmt     = "https://graph.microsoft.com/v1.0/drives/%s/items/%s:/%s"
-	itemNotFoundErrorCode   = "itemNotFound"
-	userMysiteURLNotFound   = "BadRequest Unable to retrieve user's mysite URL"
-	userMysiteNotFound      = "ResourceNotFound User's mysite not found"
-	contextDeadlineExceeded = "context deadline exceeded"
+	nextLinkKey              = "@odata.nextLink"
+	itemChildrenRawURLFmt    = "https://graph.microsoft.com/v1.0/drives/%s/items/%s/children"
+	itemByPathRawURLFmt      = "https://graph.microsoft.com/v1.0/drives/%s/items/%s:/%s"
+	itemNotFoundErrorCode    = "itemNotFound"
+	userMysiteURLNotFound    = "BadRequest Unable to retrieve user's mysite URL"
+	userMysiteURLNotFoundMsg = "Unable to retrieve user's mysite URL"
+	userMysiteNotFound       = "ResourceNotFound User's mysite not found"
+	userMysiteNotFoundMsg    = "User's mysite not found"
+	contextDeadlineExceeded  = "context deadline exceeded"
 )
 
 // DeltaUpdate holds the results of a current delta token.  It normally
@@ -91,9 +93,11 @@ func drives(
 			page, err = pager.GetPage(ctx)
 			if err != nil {
 				// Various error handling. May return an error or perform a retry.
-				detailedError := err.Error()
+				detailedError := support.ConnectorStackErrorTraceWrap(err, "").Error()
 				if strings.Contains(detailedError, userMysiteURLNotFound) ||
-					strings.Contains(detailedError, userMysiteNotFound) {
+					strings.Contains(detailedError, userMysiteURLNotFoundMsg) ||
+					strings.Contains(detailedError, userMysiteNotFound) ||
+					strings.Contains(detailedError, userMysiteNotFoundMsg) {
 					logger.Ctx(ctx).Infof("resource owner does not have a drive")
 					return make([]models.Driveable, 0), nil // no license or drives.
 				}
@@ -271,10 +275,7 @@ func getFolder(
 		err       error
 	)
 
-	err = graph.RunWithRetry(func() error {
-		foundItem, err = builder.Get(ctx, nil)
-		return err
-	})
+	foundItem, err = builder.Get(ctx, nil)
 
 	if err != nil {
 		var oDataError *odataerrors.ODataError
diff --git a/src/internal/connector/sharepoint/api/pages.go b/src/internal/connector/sharepoint/api/pages.go
index 45b32ddd5..f9d765f28 100644
--- a/src/internal/connector/sharepoint/api/pages.go
+++ b/src/internal/connector/sharepoint/api/pages.go
@@ -10,7 +10,6 @@ import (
 	"github.com/pkg/errors"
 
 	discover "github.com/alcionai/corso/src/internal/connector/discovery/api"
-	"github.com/alcionai/corso/src/internal/connector/graph"
 	"github.com/alcionai/corso/src/internal/connector/graph/betasdk/models"
 	"github.com/alcionai/corso/src/internal/connector/graph/betasdk/sites"
 	"github.com/alcionai/corso/src/internal/connector/support"
@@ -60,10 +59,7 @@ func GetSitePages(
 
 			var page models.SitePageable
 
-			err = graph.RunWithRetry(func() error {
-				page, err = serv.Client().SitesById(siteID).PagesById(pageID).Get(ctx, opts)
-				return err
-			})
+			page, err = serv.Client().SitesById(siteID).PagesById(pageID).Get(ctx, opts)
 			if err != nil {
 				errUpdater(pageID, errors.Wrap(err, support.ConnectorStackErrorTrace(err)+" fetching page"))
 			} else {
@@ -92,10 +88,7 @@ func FetchPages(ctx context.Context, bs *discover.BetaService, siteID string) ([
 	)
 
 	for {
-		err = graph.RunWithRetry(func() error {
-			resp, err = builder.Get(ctx, opts)
-			return err
-		})
+		resp, err = builder.Get(ctx, opts)
 		if err != nil {
 			return nil, support.ConnectorStackErrorTraceWrap(err, "failed fetching site page")
 		}
diff --git a/src/internal/connector/sharepoint/list.go b/src/internal/connector/sharepoint/list.go
index 64183c3a9..55d7a8530 100644
--- a/src/internal/connector/sharepoint/list.go
+++ b/src/internal/connector/sharepoint/list.go
@@ -127,10 +127,7 @@ func loadSiteLists(
 				err   error
 			)
 
-			err = graph.RunWithRetry(func() error {
-				entry, err = gs.Client().SitesById(siteID).ListsById(id).Get(ctx, nil)
-				return err
-			})
+			entry, err = gs.Client().SitesById(siteID).ListsById(id).Get(ctx, nil)
 			if err != nil {
 				errUpdater(id, support.ConnectorStackErrorTraceWrap(err, ""))
 				return