diff --git a/src/pkg/account/m365.go b/src/pkg/account/m365.go
index a9c84fb37..b9f91b8aa 100644
--- a/src/pkg/account/m365.go
+++ b/src/pkg/account/m365.go
@@ -1,6 +1,7 @@
 package account
 
 import (
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 
 	"github.com/alcionai/corso/src/pkg/credentials"
@@ -66,7 +67,7 @@ func (c M365Config) validate() error {
 
 	for k, v := range check {
 		if len(v) == 0 {
-			return errors.Wrap(errMissingRequired, k)
+			return clues.Stack(errMissingRequired, errors.New(k))
 		}
 	}
 
diff --git a/src/pkg/credentials/aws.go b/src/pkg/credentials/aws.go
index 61c0673aa..9ab9d7c3e 100644
--- a/src/pkg/credentials/aws.go
+++ b/src/pkg/credentials/aws.go
@@ -3,6 +3,7 @@ package credentials
 import (
 	"os"
 
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 )
 
@@ -48,7 +49,7 @@ func (c AWS) Validate() error {
 
 	for k, v := range check {
 		if len(v) == 0 {
-			return errors.Wrap(errMissingRequired, k)
+			return clues.Stack(errMissingRequired, errors.New(k))
 		}
 	}
 
diff --git a/src/pkg/credentials/corso.go b/src/pkg/credentials/corso.go
index 297f2030a..fc22dc957 100644
--- a/src/pkg/credentials/corso.go
+++ b/src/pkg/credentials/corso.go
@@ -3,6 +3,7 @@ package credentials
 import (
 	"os"
 
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 )
 
@@ -34,7 +35,7 @@ func (c Corso) Validate() error {
 
 	for k, v := range check {
 		if len(v) == 0 {
-			return errors.Wrap(errMissingRequired, k)
+			return clues.Stack(errMissingRequired, errors.New(k))
 		}
 	}
 
diff --git a/src/pkg/credentials/m365.go b/src/pkg/credentials/m365.go
index 2d0943aa7..c2d0c5906 100644
--- a/src/pkg/credentials/m365.go
+++ b/src/pkg/credentials/m365.go
@@ -3,6 +3,7 @@ package credentials
 import (
 	"os"
 
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 )
 
@@ -36,7 +37,7 @@ func (c M365) Validate() error {
 
 	for k, v := range check {
 		if len(v) == 0 {
-			return errors.Wrap(errMissingRequired, k)
+			return clues.Stack(errMissingRequired, errors.New(k))
 		}
 	}
 
diff --git a/src/pkg/path/onedrive.go b/src/pkg/path/onedrive.go
index cf960933f..86d40c887 100644
--- a/src/pkg/path/onedrive.go
+++ b/src/pkg/path/onedrive.go
@@ -1,8 +1,6 @@
 package path
 
-import (
-	"github.com/pkg/errors"
-)
+import "github.com/alcionai/clues"
 
 // drivePath is used to represent path components
 // of an item within the drive i.e.
@@ -20,10 +18,9 @@ func ToOneDrivePath(p Path) (*DrivePath, error) {
 
 	// Must be at least `drives/<driveID>/root:`
 	if len(folders) < 3 {
-		return nil, errors.Errorf(
-			"folder path doesn't match expected format for OneDrive items: %s",
-			p.Folder(),
-		)
+		return nil, clues.
+			New("folder path doesn't match expected format for OneDrive items").
+			With("folders", p.Folder())
 	}
 
 	return &DrivePath{DriveID: folders[1], Folders: folders[3:]}, nil
diff --git a/src/pkg/path/path.go b/src/pkg/path/path.go
index e2e6d273e..b0c4456c4 100644
--- a/src/pkg/path/path.go
+++ b/src/pkg/path/path.go
@@ -56,11 +56,10 @@ import (
 	"fmt"
 	"strings"
 
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 )
 
-const templateErrPathParsing = "parsing resource path from %s"
-
 const (
 	escapeCharacter = '\\'
 	PathSeparator   = '/'
@@ -73,7 +72,10 @@ var charactersToEscape = map[rune]struct{}{
 	escapeCharacter: {},
 }
 
-var errMissingSegment = errors.New("missing required path element")
+var (
+	errMissingSegment = errors.New("missing required path element")
+	errParsingPath    = errors.New("parsing resource path")
+)
 
 // For now, adding generic functions to pull information from segments.
 // Resources that don't have the requested information should return an empty
@@ -252,11 +254,11 @@ func (pb Builder) join(start, end int) string {
 
 func verifyInputValues(tenant, resourceOwner string) error {
 	if len(tenant) == 0 {
-		return errors.Wrap(errMissingSegment, "tenant")
+		return clues.Stack(errMissingSegment, errors.New("tenant"))
 	}
 
 	if len(resourceOwner) == 0 {
-		return errors.Wrap(errMissingSegment, "resourceOwner")
+		return clues.Stack(errMissingSegment, errors.New("resourceOwner"))
 	}
 
 	return nil
@@ -418,17 +420,17 @@ func FromDataLayerPath(p string, isItem bool) (Path, error) {
 	p = TrimTrailingSlash(p)
 	// If p was just the path separator then it will be empty now.
 	if len(p) == 0 {
-		return nil, errors.Errorf("logically empty path given: %s", p)
+		return nil, clues.New("logically empty path given").With("path_string", p)
 	}
 
 	// Turn into a Builder to reuse code that ignores empty elements.
 	pb, err := Builder{}.UnescapeAndAppend(Split(p)...)
 	if err != nil {
-		return nil, errors.Wrapf(err, templateErrPathParsing, p)
+		return nil, clues.Stack(errParsingPath, err).With("path_string", p)
 	}
 
 	if len(pb.elements) < 5 {
-		return nil, errors.Errorf("path has too few segments: %s", p)
+		return nil, clues.New("path has too few segments").With("path_string", p)
 	}
 
 	service, category, err := validateServiceAndCategoryStrings(
@@ -436,7 +438,7 @@ func FromDataLayerPath(p string, isItem bool) (Path, error) {
 		pb.elements[3],
 	)
 	if err != nil {
-		return nil, errors.Wrapf(err, templateErrPathParsing, p)
+		return nil, clues.Stack(errParsingPath, err).With("path_string", p)
 	}
 
 	return &dataLayerResourcePath{
@@ -519,8 +521,8 @@ func validateEscapedElement(element string) error {
 			prevWasEscape = false
 
 			if _, ok := charactersToEscape[c]; !ok {
-				return errors.Errorf(
-					"bad escape sequence in path: '%c%c'", escapeCharacter, c)
+				return clues.New("bad escape sequence in path").
+					With("escape_sequence", fmt.Sprintf("'%c%c'", escapeCharacter, c))
 			}
 
 		case false:
@@ -530,7 +532,7 @@ func validateEscapedElement(element string) error {
 			}
 
 			if _, ok := charactersToEscape[c]; ok {
-				return errors.Errorf("unescaped '%c' in path", c)
+				return clues.New("unescaped character in path").With("character", c)
 			}
 		}
 	}
diff --git a/src/pkg/path/resource_path.go b/src/pkg/path/resource_path.go
index 07f9f429c..57f41c6ff 100644
--- a/src/pkg/path/resource_path.go
+++ b/src/pkg/path/resource_path.go
@@ -1,8 +1,10 @@
 package path
 
 import (
+	"fmt"
 	"strings"
 
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 )
 
@@ -119,12 +121,12 @@ var serviceCategories = map[ServiceType]map[CategoryType]struct{}{
 func validateServiceAndCategoryStrings(s, c string) (ServiceType, CategoryType, error) {
 	service := toServiceType(s)
 	if service == UnknownService {
-		return UnknownService, UnknownCategory, errors.Wrapf(ErrorUnknownService, "%q", s)
+		return UnknownService, UnknownCategory, clues.Stack(ErrorUnknownService).With("service", fmt.Sprintf("%q", s))
 	}
 
 	category := ToCategoryType(c)
 	if category == UnknownCategory {
-		return UnknownService, UnknownCategory, errors.Wrapf(ErrorUnknownCategory, "%q", c)
+		return UnknownService, UnknownCategory, clues.Stack(ErrorUnknownService).With("category", fmt.Sprintf("%q", c))
 	}
 
 	if err := validateServiceAndCategory(service, category); err != nil {
@@ -137,15 +139,12 @@ func validateServiceAndCategoryStrings(s, c string) (ServiceType, CategoryType,
 func validateServiceAndCategory(service ServiceType, category CategoryType) error {
 	cats, ok := serviceCategories[service]
 	if !ok {
-		return errors.New("unsupported service")
+		return clues.New("unsupported service").With("service", fmt.Sprintf("%q", service))
 	}
 
 	if _, ok := cats[category]; !ok {
-		return errors.Errorf(
-			"unknown service/category combination %q/%q",
-			service,
-			category,
-		)
+		return clues.New("unknown service/category combination").
+			WithAll("service", fmt.Sprintf("%q", service), "category", fmt.Sprintf("%q", category))
 	}
 
 	return nil
@@ -234,7 +233,7 @@ func (rp dataLayerResourcePath) Item() string {
 
 func (rp dataLayerResourcePath) Dir() (Path, error) {
 	if len(rp.elements) <= 4 {
-		return nil, errors.Errorf("unable to shorten path %q", rp)
+		return nil, clues.New("unable to shorten path").With("path", fmt.Sprintf("%q", rp))
 	}
 
 	return &dataLayerResourcePath{
diff --git a/src/pkg/repository/repository.go b/src/pkg/repository/repository.go
index 087b193bc..a8f1e2827 100644
--- a/src/pkg/repository/repository.go
+++ b/src/pkg/repository/repository.go
@@ -89,13 +89,17 @@ func Initialize(
 	s storage.Storage,
 	opts control.Options,
 ) (Repository, error) {
-	ctx = clues.AddAll(ctx, "acct_provider", acct.Provider, "storage_provider", s.Provider)
+	ctx = clues.AddAll(
+		ctx,
+		"acct_provider", acct.Provider.String(),
+		"acct_id", acct.ID(), // TODO: pii
+		"storage_provider", s.Provider.String())
 
 	kopiaRef := kopia.NewConn(s)
 	if err := kopiaRef.Initialize(ctx); err != nil {
 		// replace common internal errors so that sdk users can check results with errors.Is()
 		if kopia.IsRepoAlreadyExistsError(err) {
-			return nil, ErrorRepoAlreadyExists
+			return nil, clues.Stack(ErrorRepoAlreadyExists).WithClues(ctx)
 		}
 
 		return nil, errors.Wrap(err, "initializing kopia")
@@ -153,7 +157,11 @@ func Connect(
 	s storage.Storage,
 	opts control.Options,
 ) (Repository, error) {
-	ctx = clues.AddAll(ctx, "acct_provider", acct.Provider, "storage_provider", s.Provider)
+	ctx = clues.AddAll(
+		ctx,
+		"acct_provider", acct.Provider.String(),
+		"acct_id", acct.ID(), // TODO: pii
+		"storage_provider", s.Provider.String())
 
 	// Close/Reset the progress bar. This ensures callers don't have to worry about
 	// their output getting clobbered (#1720)
@@ -210,12 +218,12 @@ func Connect(
 
 func (r *repository) Close(ctx context.Context) error {
 	if err := r.Bus.Close(); err != nil {
-		logger.Ctx(ctx).Debugw("closing the event bus", "err", err)
+		logger.Ctx(ctx).With("err", err).Debugw("closing the event bus", clues.In(ctx).Slice()...)
 	}
 
 	if r.dataLayer != nil {
 		if err := r.dataLayer.Close(ctx); err != nil {
-			logger.Ctx(ctx).Debugw("closing Datalayer", "err", err)
+			logger.Ctx(ctx).With("err", err).Debugw("closing Datalayer", clues.In(ctx).Slice()...)
 		}
 
 		r.dataLayer = nil
@@ -223,7 +231,7 @@ func (r *repository) Close(ctx context.Context) error {
 
 	if r.modelStore != nil {
 		if err := r.modelStore.Close(ctx); err != nil {
-			logger.Ctx(ctx).Debugw("closing modelStore", "err", err)
+			logger.Ctx(ctx).With("err", err).Debugw("closing modelStore", clues.In(ctx).Slice()...)
 		}
 
 		r.modelStore = nil
diff --git a/src/pkg/services/m365/m365.go b/src/pkg/services/m365/m365.go
index 984326b6d..19d37f0d5 100644
--- a/src/pkg/services/m365/m365.go
+++ b/src/pkg/services/m365/m365.go
@@ -3,6 +3,7 @@ package m365
 import (
 	"context"
 
+	"github.com/alcionai/clues"
 	"github.com/microsoftgraph/msgraph-sdk-go/models"
 	"github.com/pkg/errors"
 
@@ -20,10 +21,10 @@ type User struct {
 
 // Users returns a list of users in the specified M365 tenant
 // TODO: Implement paging support
-func Users(ctx context.Context, m365Account account.Account) ([]*User, error) {
-	gc, err := connector.NewGraphConnector(ctx, graph.HTTPClient(graph.NoTimeout()), m365Account, connector.Users)
+func Users(ctx context.Context, acct account.Account) ([]*User, error) {
+	gc, err := connector.NewGraphConnector(ctx, graph.HTTPClient(graph.NoTimeout()), acct, connector.Users)
 	if err != nil {
-		return nil, errors.Wrap(err, "could not initialize M365 graph connection")
+		return nil, errors.Wrap(err, "initializing M365 graph connection")
 	}
 
 	users, err := discovery.Users(ctx, gc.Owners.Users())
@@ -36,7 +37,7 @@ func Users(ctx context.Context, m365Account account.Account) ([]*User, error) {
 	for _, u := range users {
 		pu, err := parseUser(u)
 		if err != nil {
-			return nil, err
+			return nil, errors.Wrap(err, "parsing userable")
 		}
 
 		ret = append(ret, pu)
@@ -45,8 +46,8 @@ func Users(ctx context.Context, m365Account account.Account) ([]*User, error) {
 	return ret, nil
 }
 
-func UserIDs(ctx context.Context, m365Account account.Account) ([]string, error) {
-	users, err := Users(ctx, m365Account)
+func UserIDs(ctx context.Context, acct account.Account) ([]string, error) {
+	users, err := Users(ctx, acct)
 	if err != nil {
 		return nil, err
 	}
@@ -61,8 +62,8 @@ func UserIDs(ctx context.Context, m365Account account.Account) ([]string, error)
 
 // UserPNs retrieves all user principleNames in the tenant.  Principle Names
 // can be used analogous userIDs in graph API queries.
-func UserPNs(ctx context.Context, m365Account account.Account) ([]string, error) {
-	users, err := Users(ctx, m365Account)
+func UserPNs(ctx context.Context, acct account.Account) ([]string, error) {
+	users, err := Users(ctx, acct)
 	if err != nil {
 		return nil, err
 	}
@@ -76,20 +77,20 @@ func UserPNs(ctx context.Context, m365Account account.Account) ([]string, error)
 }
 
 // SiteURLs returns a list of SharePoint site WebURLs in the specified M365 tenant
-func SiteURLs(ctx context.Context, m365Account account.Account) ([]string, error) {
-	gc, err := connector.NewGraphConnector(ctx, graph.HTTPClient(graph.NoTimeout()), m365Account, connector.Sites)
+func SiteURLs(ctx context.Context, acct account.Account) ([]string, error) {
+	gc, err := connector.NewGraphConnector(ctx, graph.HTTPClient(graph.NoTimeout()), acct, connector.Sites)
 	if err != nil {
-		return nil, errors.Wrap(err, "could not initialize M365 graph connection")
+		return nil, errors.Wrap(err, "initializing M365 graph connection")
 	}
 
 	return gc.GetSiteWebURLs(), nil
 }
 
 // SiteURLs returns a list of SharePoint sites IDs in the specified M365 tenant
-func SiteIDs(ctx context.Context, m365Account account.Account) ([]string, error) {
-	gc, err := connector.NewGraphConnector(ctx, graph.HTTPClient(graph.NoTimeout()), m365Account, connector.Sites)
+func SiteIDs(ctx context.Context, acct account.Account) ([]string, error) {
+	gc, err := connector.NewGraphConnector(ctx, graph.HTTPClient(graph.NoTimeout()), acct, connector.Sites)
 	if err != nil {
-		return nil, errors.Wrap(err, "could not initialize M365 graph connection")
+		return nil, errors.Wrap(err, "initializing graph connection")
 	}
 
 	return gc.GetSiteIDs(), nil
@@ -98,7 +99,8 @@ func SiteIDs(ctx context.Context, m365Account account.Account) ([]string, error)
 // parseUser extracts information from `models.Userable` we care about
 func parseUser(item models.Userable) (*User, error) {
 	if item.GetUserPrincipalName() == nil {
-		return nil, errors.Errorf("no principal name for User: %s", *item.GetId())
+		return nil, clues.New("user missing principal name").
+			With("user_id", *item.GetId()) // TODO: pii
 	}
 
 	u := &User{PrincipalName: *item.GetUserPrincipalName(), ID: *item.GetId()}
diff --git a/src/pkg/storage/common.go b/src/pkg/storage/common.go
index fd5bb24dd..e230e50fb 100644
--- a/src/pkg/storage/common.go
+++ b/src/pkg/storage/common.go
@@ -1,6 +1,7 @@
 package storage
 
 import (
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 
 	"github.com/alcionai/corso/src/pkg/credentials"
@@ -45,7 +46,7 @@ func (s Storage) CommonConfig() (CommonConfig, error) {
 // ensures all required properties are present
 func (c CommonConfig) validate() error {
 	if len(c.CorsoPassphrase) == 0 {
-		return errors.Wrap(errMissingRequired, credentials.CorsoPassphrase)
+		return clues.Stack(errMissingRequired, errors.New(credentials.CorsoPassphrase))
 	}
 
 	// kopiaCfgFilePath is not required
diff --git a/src/pkg/storage/s3.go b/src/pkg/storage/s3.go
index 67711f421..78de67ce3 100644
--- a/src/pkg/storage/s3.go
+++ b/src/pkg/storage/s3.go
@@ -3,6 +3,7 @@ package storage
 import (
 	"strconv"
 
+	"github.com/alcionai/clues"
 	"github.com/pkg/errors"
 
 	"github.com/alcionai/corso/src/internal/common"
@@ -81,7 +82,7 @@ func (c S3Config) validate() error {
 	}
 	for k, v := range check {
 		if len(v) == 0 {
-			return errors.Wrap(errMissingRequired, k)
+			return clues.Stack(errMissingRequired, errors.New(k))
 		}
 	}