diff --git a/pkg/ccl/kvccl/kvtenantccl/connector.go b/pkg/ccl/kvccl/kvtenantccl/connector.go
index dd3c760efce9..16e64f1da835 100644
--- a/pkg/ccl/kvccl/kvtenantccl/connector.go
+++ b/pkg/ccl/kvccl/kvtenantccl/connector.go
@@ -416,7 +416,7 @@ func (c *Connector) RangeLookup(
 		}
 		return resp.Descriptors, resp.PrefetchedDescriptors, nil
 	}
-	return nil, nil, ctx.Err()
+	return nil, nil, errors.Wrap(ctx.Err(), "range lookup")
 }
 
 // Regions implements the serverpb.RegionsServer interface.
@@ -482,7 +482,7 @@ func (c *Connector) TokenBucket(
 		}
 		return resp, nil
 	}
-	return nil, ctx.Err()
+	return nil, errors.Wrap(ctx.Err(), "token bucket")
 }
 
 // GetSpanConfigRecords implements the spanconfig.KVAccessor interface.
@@ -494,7 +494,7 @@ func (c *Connector) GetSpanConfigRecords(
 			Targets: spanconfig.TargetsToProtos(targets),
 		})
 		if err != nil {
-			return err
+			return errors.Wrap(err, "get span configs error")
 		}
 
 		records, err = spanconfig.EntriesToRecords(resp.SpanConfigEntries)
@@ -524,7 +524,7 @@ func (c *Connector) UpdateSpanConfigRecords(
 			MaxCommitTimestamp: maxCommitTS,
 		})
 		if err != nil {
-			return err
+			return errors.Wrap(err, "update span configs error")
 		}
 		if resp.Error.IsSet() {
 			// Logical error; propagate as such.
@@ -541,13 +541,12 @@ func (c *Connector) GetAllSystemSpanConfigsThatApply(
 ) ([]roachpb.SpanConfig, error) {
 	var spanConfigs []roachpb.SpanConfig
 	if err := c.withClient(ctx, func(ctx context.Context, c *client) error {
-		var err error
 		resp, err := c.GetAllSystemSpanConfigsThatApply(
 			ctx, &roachpb.GetAllSystemSpanConfigsThatApplyRequest{
 				TenantID: id,
 			})
 		if err != nil {
-			return err
+			return errors.Wrap(err, "get all system span configs that apply error")
 		}
 
 		spanConfigs = resp.SpanConfigs
@@ -576,7 +575,7 @@ func (c *Connector) withClient(
 		}
 		return f(ctx, c)
 	}
-	return ctx.Err()
+	return errors.Wrap(ctx.Err(), "with client")
 }
 
 // getClient returns the singleton InternalClient if one is currently active. If
@@ -639,7 +638,7 @@ func (c *Connector) dialAddrs(ctx context.Context) (*client, error) {
 			}, nil
 		}
 	}
-	return nil, ctx.Err()
+	return nil, errors.Wrap(ctx.Err(), "dial addrs")
 }
 
 func (c *Connector) dialAddr(ctx context.Context, addr string) (conn *grpc.ClientConn, err error) {
diff --git a/pkg/kv/kvclient/kvcoord/transport.go b/pkg/kv/kvclient/kvcoord/transport.go
index 83cfbffa0d34..4530227c189c 100644
--- a/pkg/kv/kvclient/kvcoord/transport.go
+++ b/pkg/kv/kvclient/kvcoord/transport.go
@@ -225,7 +225,10 @@ func (gt *grpcTransport) sendBatch(
 			span.ImportRemoteSpans(reply.CollectedSpans)
 		}
 	}
-	return reply, err
+	if err != nil {
+		return nil, errors.Wrapf(err, "ba: %s RPC error", ba.String())
+	}
+	return reply, nil
 }
 
 // NextInternalClient returns the next InternalClient to use for performing
diff --git a/pkg/kv/kvnemesis/applier_test.go b/pkg/kv/kvnemesis/applier_test.go
index 5df5f14889ac..fff1cc9c1853 100644
--- a/pkg/kv/kvnemesis/applier_test.go
+++ b/pkg/kv/kvnemesis/applier_test.go
@@ -60,7 +60,7 @@ func TestApplier(t *testing.T) {
 		// Trim out context canceled location, which can be non-deterministic.
 		// The wrapped string around the context canceled error depends on where
 		// the context cancellation was noticed.
-		actual = regexp.MustCompile(` aborted .*: context canceled`).ReplaceAllString(actual, ` context canceled`)
+		actual = regexp.MustCompile(` (aborted .*|txn exec): context canceled`).ReplaceAllString(actual, ` context canceled`)
 		assert.Equal(t, strings.TrimSpace(expected), strings.TrimSpace(actual))
 	}
 
diff --git a/pkg/kv/txn.go b/pkg/kv/txn.go
index a37f5135adcf..207b1578c6ab 100644
--- a/pkg/kv/txn.go
+++ b/pkg/kv/txn.go
@@ -988,7 +988,7 @@ func (txn *Txn) exec(ctx context.Context, fn func(context.Context, *Txn) error)
 	// error condition this loop isn't capable of handling.
 	for {
 		if err := ctx.Err(); err != nil {
-			return err
+			return errors.Wrap(err, "txn exec")
 		}
 		err = fn(ctx, txn)
 
diff --git a/pkg/rpc/context.go b/pkg/rpc/context.go
index c071a1e8654f..9725cbe07392 100644
--- a/pkg/rpc/context.go
+++ b/pkg/rpc/context.go
@@ -319,7 +319,7 @@ func (c *Connection) Connect(ctx context.Context) (*grpc.ClientConn, error) {
 	case <-c.stopper.ShouldQuiesce():
 		return nil, errors.Errorf("stopped")
 	case <-ctx.Done():
-		return nil, ctx.Err()
+		return nil, errors.Wrap(ctx.Err(), "connect")
 	}
 
 	// If connection is invalid, return latest heartbeat error.
diff --git a/pkg/rpc/nodedialer/nodedialer.go b/pkg/rpc/nodedialer/nodedialer.go
index 7b50ce91b365..1667ab938f02 100644
--- a/pkg/rpc/nodedialer/nodedialer.go
+++ b/pkg/rpc/nodedialer/nodedialer.go
@@ -106,7 +106,7 @@ func (n *Dialer) Dial(
 	}
 	// Don't trip the breaker if we're already canceled.
 	if ctxErr := ctx.Err(); ctxErr != nil {
-		return nil, ctxErr
+		return nil, errors.Wrap(ctxErr, "dial")
 	}
 	breaker := n.getBreaker(nodeID, class)
 	addr, err := n.resolver(nodeID)
@@ -185,9 +185,10 @@ func (n *Dialer) dial(
 	checkBreaker bool,
 	class rpc.ConnectionClass,
 ) (_ *grpc.ClientConn, err error) {
+	const ctxWrapMsg = "dial"
 	// Don't trip the breaker if we're already canceled.
 	if ctxErr := ctx.Err(); ctxErr != nil {
-		return nil, ctxErr
+		return nil, errors.Wrap(ctxErr, ctxWrapMsg)
 	}
 	if checkBreaker && !breaker.Ready() {
 		err = errors.Wrapf(circuit.ErrBreakerOpen, "unable to dial n%d", nodeID)
@@ -203,7 +204,7 @@ func (n *Dialer) dial(
 	if err != nil {
 		// If we were canceled during the dial, don't trip the breaker.
 		if ctxErr := ctx.Err(); ctxErr != nil {
-			return nil, ctxErr
+			return nil, errors.Wrap(ctxErr, ctxWrapMsg)
 		}
 		err = errors.Wrapf(err, "failed to connect to n%d at %v", nodeID, addr)
 		if breaker != nil {
diff --git a/pkg/server/init.go b/pkg/server/init.go
index fbcdcc608af4..aaa077e3745c 100644
--- a/pkg/server/init.go
+++ b/pkg/server/init.go
@@ -472,7 +472,7 @@ func (s *initServer) attemptJoinTo(
 
 		status, ok := grpcstatus.FromError(errors.UnwrapAll(err))
 		if !ok {
-			return nil, err
+			return nil, errors.Wrap(err, "failed to join cluster")
 		}
 
 		// TODO(irfansharif): Here we're logging the error and also returning
diff --git a/pkg/sql/internal_result_channel.go b/pkg/sql/internal_result_channel.go
index d8e4a282dddc..d85cb8bf370e 100644
--- a/pkg/sql/internal_result_channel.go
+++ b/pkg/sql/internal_result_channel.go
@@ -111,14 +111,16 @@ func newSyncIEResultChannel() *ieResultChannel {
 func (i *ieResultChannel) firstResult(
 	ctx context.Context,
 ) (_ ieIteratorResult, done bool, err error) {
+	// errors.Wrap returns nil if ctx.Err() is nil.
+	const wrapMsg = "failed to read query result"
 	select {
 	case <-ctx.Done():
-		return ieIteratorResult{}, true, ctx.Err()
+		return ieIteratorResult{}, true, errors.Wrap(ctx.Err(), wrapMsg)
 	case <-i.doneCh:
-		return ieIteratorResult{}, true, ctx.Err()
+		return ieIteratorResult{}, true, errors.Wrap(ctx.Err(), wrapMsg)
 	case res, ok := <-i.dataCh:
 		if !ok {
-			return ieIteratorResult{}, true, ctx.Err()
+			return ieIteratorResult{}, true, errors.Wrap(ctx.Err(), wrapMsg)
 		}
 		return res, false, nil
 	}
@@ -128,11 +130,13 @@ func (i *ieResultChannel) maybeUnblockWriter(ctx context.Context) (done bool, er
 	if i.async() {
 		return false, nil
 	}
+	// errors.Wrap returns nil if ctx.Err() is nil.
+	const wrapMsg = "maybe unblock writer"
 	select {
 	case <-ctx.Done():
-		return true, ctx.Err()
+		return true, errors.Wrap(ctx.Err(), wrapMsg)
 	case <-i.doneCh:
-		return true, ctx.Err()
+		return true, errors.Wrap(ctx.Err(), wrapMsg)
 	case i.waitCh <- struct{}{}:
 		return false, nil
 	}
@@ -181,13 +185,15 @@ func (i *ieResultChannel) close() error {
 var errIEResultChannelClosed = errors.New("ieResultReader closed")
 
 func (i *ieResultChannel) addResult(ctx context.Context, result ieIteratorResult) error {
+	// errors.Wrap returns nil if ctx.Err() is nil.
+	const wrapMsg = "add result"
 	select {
 	case <-ctx.Done():
-		return ctx.Err()
+		return errors.Wrap(ctx.Err(), wrapMsg)
 	case <-i.doneCh:
 		// Prefer the context error if there is one.
 		if ctxErr := ctx.Err(); ctxErr != nil {
-			return ctxErr
+			return errors.Wrap(ctx.Err(), wrapMsg)
 		}
 		return errIEResultChannelClosed
 	case i.dataCh <- result:
@@ -196,16 +202,18 @@ func (i *ieResultChannel) addResult(ctx context.Context, result ieIteratorResult
 }
 
 func (i *ieResultChannel) maybeBlock(ctx context.Context) error {
+	// errors.Wrap returns nil if ctx.Err() is nil.
+	const wrapMsg = "maybe block"
 	if i.async() {
 		return nil
 	}
 	select {
 	case <-ctx.Done():
-		return ctx.Err()
+		return errors.Wrap(ctx.Err(), wrapMsg)
 	case <-i.doneCh:
 		// Prefer the context error if there is one.
 		if ctxErr := ctx.Err(); ctxErr != nil {
-			return ctxErr
+			return errors.Wrap(ctxErr, wrapMsg)
 		}
 		return errIEResultChannelClosed
 	case <-i.waitCh:
diff --git a/pkg/sql/user.go b/pkg/sql/user.go
index 81318f01b4c4..9b7d1fecb475 100644
--- a/pkg/sql/user.go
+++ b/pkg/sql/user.go
@@ -85,7 +85,7 @@ func GetUserSessionInitInfo(
 	pwRetrieveFn func(ctx context.Context) (expired bool, hashedPassword security.PasswordHash, err error),
 	err error,
 ) {
-	runFn := getUserInfoRunFn(execCfg, username, "get-user-timeout")
+	runFn := getUserInfoRunFn(execCfg, username, "get-user-session")
 
 	if username.IsRootUser() {
 		// As explained above, for root we report that the user exists
@@ -215,7 +215,7 @@ func retrieveSessionInitInfoWithCache(
 			retrieveAuthInfo,
 		)
 		if retErr != nil {
-			return retErr
+			return errors.Wrap(retErr, "get auth info error")
 		}
 		// Avoid looking up default settings for root and non-existent users.
 		if username.IsRootUser() || !aInfo.UserExists {
@@ -231,7 +231,7 @@ func retrieveSessionInitInfoWithCache(
 			databaseName,
 			retrieveDefaultSettings,
 		)
-		return retErr
+		return errors.Wrap(retErr, "get default settings error")
 	}(); err != nil {
 		// Failed to retrieve the user account. Report in logs for later investigation.
 		log.Warningf(ctx, "user lookup for %q failed: %v", username, err)
@@ -678,7 +678,7 @@ func updateUserPasswordHash(
 	username security.SQLUsername,
 	prevHash, newHash []byte,
 ) error {
-	runFn := getUserInfoRunFn(execCfg, username, "set-hash-timeout")
+	runFn := getUserInfoRunFn(execCfg, username, "set-user-password-hash")
 
 	return runFn(ctx, func(ctx context.Context) error {
 		return DescsTxn(ctx, execCfg, func(ctx context.Context, txn *kv.Txn, d *descs.Collection) error {
diff --git a/pkg/util/limit/limiter.go b/pkg/util/limit/limiter.go
index b36a313e2b5f..264d94afed28 100644
--- a/pkg/util/limit/limiter.go
+++ b/pkg/util/limit/limiter.go
@@ -46,7 +46,7 @@ func MakeConcurrentRequestLimiter(spanName string, limit int) ConcurrentRequestL
 // is forced to block.
 func (l *ConcurrentRequestLimiter) Begin(ctx context.Context) (Reservation, error) {
 	if err := ctx.Err(); err != nil {
-		return nil, err
+		return nil, errors.Wrap(err, "limiter begin")
 	}
 
 	res, err := l.sem.TryAcquire(ctx, 1)
diff --git a/pkg/util/tracing/grpc_interceptor.go b/pkg/util/tracing/grpc_interceptor.go
index 87247f42bd04..4fffa62b53cc 100644
--- a/pkg/util/tracing/grpc_interceptor.go
+++ b/pkg/util/tracing/grpc_interceptor.go
@@ -18,6 +18,7 @@ import (
 	"sync/atomic"
 
 	"github.com/cockroachdb/cockroach/pkg/util/tracing/tracingpb"
+	"github.com/cockroachdb/errors"
 	"go.opentelemetry.io/otel/attribute"
 	"go.opentelemetry.io/otel/codes"
 	"google.golang.org/grpc"
@@ -131,7 +132,7 @@ func ServerInterceptor(tracer *Tracer) grpc.UnaryServerInterceptor {
 		req interface{},
 		info *grpc.UnaryServerInfo,
 		handler grpc.UnaryHandler,
-	) (resp interface{}, err error) {
+	) (interface{}, error) {
 		if methodExcludedFromTracing(info.FullMethod) {
 			return handler(ctx, req)
 		}
@@ -152,7 +153,7 @@ func ServerInterceptor(tracer *Tracer) grpc.UnaryServerInterceptor {
 		)
 		defer serverSpan.Finish()
 
-		resp, err = handler(ctx, req)
+		resp, err := handler(ctx, req)
 		if err != nil {
 			setGRPCErrorTag(serverSpan, err)
 			serverSpan.Recordf("error: %s", err)
@@ -295,15 +296,15 @@ func ClientInterceptor(
 		if compatibilityMode(ctx) || !methodExcludedFromTracing(method) {
 			ctx = injectSpanMeta(ctx, tracer, clientSpan)
 		}
-		var err error
 		if invoker != nil {
-			err = invoker(ctx, method, req, resp, cc, opts...)
-		}
-		if err != nil {
-			setGRPCErrorTag(clientSpan, err)
-			clientSpan.Recordf("error: %s", err)
+			err := invoker(ctx, method, req, resp, cc, opts...)
+			if err != nil {
+				setGRPCErrorTag(clientSpan, err)
+				clientSpan.Recordf("error: %s", err)
+				return err
+			}
 		}
-		return err
+		return nil
 	}
 }
 
@@ -425,7 +426,7 @@ func (cs *tracingClientStream) Header() (metadata.MD, error) {
 	if err != nil {
 		cs.finishFunc(err)
 	}
-	return md, err
+	return md, errors.Wrap(err, "header error")
 }
 
 func (cs *tracingClientStream) SendMsg(m interface{}) error {
@@ -433,22 +434,21 @@ func (cs *tracingClientStream) SendMsg(m interface{}) error {
 	if err != nil {
 		cs.finishFunc(err)
 	}
-	return err
+	return errors.Wrap(err, "send msg error")
 }
 
 func (cs *tracingClientStream) RecvMsg(m interface{}) error {
 	err := cs.ClientStream.RecvMsg(m)
 	if err == io.EOF {
 		cs.finishFunc(nil)
+		// Do not wrap EOF.
 		return err
 	} else if err != nil {
 		cs.finishFunc(err)
-		return err
-	}
-	if !cs.desc.ServerStreams {
+	} else if !cs.desc.ServerStreams {
 		cs.finishFunc(nil)
 	}
-	return err
+	return errors.Wrap(err, "recv msg error")
 }
 
 func (cs *tracingClientStream) CloseSend() error {
@@ -456,7 +456,7 @@ func (cs *tracingClientStream) CloseSend() error {
 	if err != nil {
 		cs.finishFunc(err)
 	}
-	return err
+	return errors.Wrap(err, "close send error")
 }
 
 // Recording represents a group of RecordedSpans rooted at a fixed root span, as