diff --git a/agent/pkg/proto/agent.pb.go b/agent/pkg/proto/agent.pb.go
index 747934ed..5d0a89f6 100644
--- a/agent/pkg/proto/agent.pb.go
+++ b/agent/pkg/proto/agent.pb.go
@@ -405,8 +405,7 @@ type SetAllConfigRequest struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	Path   *bool                   `protobuf:"varint,1,opt,name=path,proto3,oneof" json:"path,omitempty"`                                                                                      // Parse the keys as paths in a map or list rather than raw strings
-	Config map[string]*ConfigValue `protobuf:"bytes,2,rep,name=config,proto3" json:"config,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"` // a map of ConfigValue used by Pulumi programs
+	Config []*ConfigItem `protobuf:"bytes,1,rep,name=config,proto3" json:"config,omitempty"`
 }
 
 func (x *SetAllConfigRequest) Reset() {
@@ -441,35 +440,30 @@ func (*SetAllConfigRequest) Descriptor() ([]byte, []int) {
 	return file_agent_proto_rawDescGZIP(), []int{7}
 }
 
-func (x *SetAllConfigRequest) GetPath() bool {
-	if x != nil && x.Path != nil {
-		return *x.Path
-	}
-	return false
-}
-
-func (x *SetAllConfigRequest) GetConfig() map[string]*ConfigValue {
+func (x *SetAllConfigRequest) GetConfig() []*ConfigItem {
 	if x != nil {
 		return x.Config
 	}
 	return nil
 }
 
-type ConfigValue struct {
+type ConfigItem struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
+	Key  string `protobuf:"bytes,1,opt,name=key,proto3" json:"key,omitempty"`          // The config's key.
+	Path *bool  `protobuf:"varint,2,opt,name=path,proto3,oneof" json:"path,omitempty"` // Parse the key as a paths in a map or list rather than as a raw string.
 	// Types that are assignable to V:
 	//
-	//	*ConfigValue_Value
-	//	*ConfigValue_ValueFrom
-	V      isConfigValue_V `protobuf_oneof:"v"`
-	Secret *bool           `protobuf:"varint,3,opt,name=secret,proto3,oneof" json:"secret,omitempty"`
+	//	*ConfigItem_Value
+	//	*ConfigItem_ValueFrom
+	V      isConfigItem_V `protobuf_oneof:"v"`
+	Secret *bool          `protobuf:"varint,5,opt,name=secret,proto3,oneof" json:"secret,omitempty"` // Whether the config is a secret.
 }
 
-func (x *ConfigValue) Reset() {
-	*x = ConfigValue{}
+func (x *ConfigItem) Reset() {
+	*x = ConfigItem{}
 	if protoimpl.UnsafeEnabled {
 		mi := &file_agent_proto_msgTypes[8]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
@@ -477,13 +471,13 @@ func (x *ConfigValue) Reset() {
 	}
 }
 
-func (x *ConfigValue) String() string {
+func (x *ConfigItem) String() string {
 	return protoimpl.X.MessageStringOf(x)
 }
 
-func (*ConfigValue) ProtoMessage() {}
+func (*ConfigItem) ProtoMessage() {}
 
-func (x *ConfigValue) ProtoReflect() protoreflect.Message {
+func (x *ConfigItem) ProtoReflect() protoreflect.Message {
 	mi := &file_agent_proto_msgTypes[8]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
@@ -495,54 +489,68 @@ func (x *ConfigValue) ProtoReflect() protoreflect.Message {
 	return mi.MessageOf(x)
 }
 
-// Deprecated: Use ConfigValue.ProtoReflect.Descriptor instead.
-func (*ConfigValue) Descriptor() ([]byte, []int) {
+// Deprecated: Use ConfigItem.ProtoReflect.Descriptor instead.
+func (*ConfigItem) Descriptor() ([]byte, []int) {
 	return file_agent_proto_rawDescGZIP(), []int{8}
 }
 
-func (m *ConfigValue) GetV() isConfigValue_V {
+func (x *ConfigItem) GetKey() string {
+	if x != nil {
+		return x.Key
+	}
+	return ""
+}
+
+func (x *ConfigItem) GetPath() bool {
+	if x != nil && x.Path != nil {
+		return *x.Path
+	}
+	return false
+}
+
+func (m *ConfigItem) GetV() isConfigItem_V {
 	if m != nil {
 		return m.V
 	}
 	return nil
 }
 
-func (x *ConfigValue) GetValue() *structpb.Value {
-	if x, ok := x.GetV().(*ConfigValue_Value); ok {
+func (x *ConfigItem) GetValue() *structpb.Value {
+	if x, ok := x.GetV().(*ConfigItem_Value); ok {
 		return x.Value
 	}
 	return nil
 }
 
-func (x *ConfigValue) GetValueFrom() *ConfigValueFrom {
-	if x, ok := x.GetV().(*ConfigValue_ValueFrom); ok {
+func (x *ConfigItem) GetValueFrom() *ConfigValueFrom {
+	if x, ok := x.GetV().(*ConfigItem_ValueFrom); ok {
 		return x.ValueFrom
 	}
 	return nil
 }
 
-func (x *ConfigValue) GetSecret() bool {
+func (x *ConfigItem) GetSecret() bool {
 	if x != nil && x.Secret != nil {
 		return *x.Secret
 	}
 	return false
 }
 
-type isConfigValue_V interface {
-	isConfigValue_V()
+type isConfigItem_V interface {
+	isConfigItem_V()
 }
 
-type ConfigValue_Value struct {
-	Value *structpb.Value `protobuf:"bytes,1,opt,name=value,proto3,oneof"`
+type ConfigItem_Value struct {
+	Value *structpb.Value `protobuf:"bytes,3,opt,name=value,proto3,oneof"` // A literal value.
 }
 
-type ConfigValue_ValueFrom struct {
-	ValueFrom *ConfigValueFrom `protobuf:"bytes,2,opt,name=value_from,json=valueFrom,proto3,oneof"`
+type ConfigItem_ValueFrom struct {
+	ValueFrom *ConfigValueFrom `protobuf:"bytes,4,opt,name=value_from,json=valueFrom,proto3,oneof"` // A value read from the environment or local disk.
 }
 
-func (*ConfigValue_Value) isConfigValue_V() {}
+func (*ConfigItem_Value) isConfigItem_V() {}
 
-func (*ConfigValue_ValueFrom) isConfigValue_V() {}
+func (*ConfigItem_ValueFrom) isConfigItem_V() {}
 
 type ConfigValueFrom struct {
 	state         protoimpl.MessageState
@@ -614,11 +622,11 @@ type isConfigValueFrom_F interface {
 }
 
 type ConfigValueFrom_Env struct {
-	Env string `protobuf:"bytes,1,opt,name=env,proto3,oneof"` // the name of an environment variable to read
+	Env string `protobuf:"bytes,1,opt,name=env,proto3,oneof"` // The name of an environment variable to read>
 }
 
 type ConfigValueFrom_Path struct {
-	Path string `protobuf:"bytes,2,opt,name=path,proto3,oneof"` // the path to a file to read
+	Path string `protobuf:"bytes,2,opt,name=path,proto3,oneof"` // The path to a file to read.
 }
 
 func (*ConfigValueFrom_Env) isConfigValueFrom_F() {}
@@ -2005,262 +2013,257 @@ var file_agent_proto_rawDesc = []byte{
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 }
 
 var (
@@ -2275,7 +2278,7 @@ func file_agent_proto_rawDescGZIP() []byte {
 	return file_agent_proto_rawDescData
 }
 
-var file_agent_proto_msgTypes = make([]protoimpl.MessageInfo, 30)
+var file_agent_proto_msgTypes = make([]protoimpl.MessageInfo, 29)
 var file_agent_proto_goTypes = []any{
 	(*WhoAmIRequest)(nil),         // 0: agent.WhoAmIRequest
 	(*WhoAmIResult)(nil),          // 1: agent.WhoAmIResult
@@ -2285,7 +2288,7 @@ var file_agent_proto_goTypes = []any{
 	(*InfoResult)(nil),            // 5: agent.InfoResult
 	(*StackSummary)(nil),          // 6: agent.StackSummary
 	(*SetAllConfigRequest)(nil),   // 7: agent.SetAllConfigRequest
-	(*ConfigValue)(nil),           // 8: agent.ConfigValue
+	(*ConfigItem)(nil),            // 8: agent.ConfigItem
 	(*ConfigValueFrom)(nil),       // 9: agent.ConfigValueFrom
 	(*SetAllConfigResult)(nil),    // 10: agent.SetAllConfigResult
 	(*InstallRequest)(nil),        // 11: agent.InstallRequest
@@ -2305,61 +2308,59 @@ var file_agent_proto_goTypes = []any{
 	(*DestroyRequest)(nil),        // 25: agent.DestroyRequest
 	(*DestroyStream)(nil),         // 26: agent.DestroyStream
 	(*DestroyResult)(nil),         // 27: agent.DestroyResult
-	nil,                           // 28: agent.SetAllConfigRequest.ConfigEntry
-	nil,                           // 29: agent.UpResult.OutputsEntry
-	(*timestamppb.Timestamp)(nil), // 30: google.protobuf.Timestamp
-	(*structpb.Value)(nil),        // 31: google.protobuf.Value
-	(*structpb.Struct)(nil),       // 32: google.protobuf.Struct
+	nil,                           // 28: agent.UpResult.OutputsEntry
+	(*timestamppb.Timestamp)(nil), // 29: google.protobuf.Timestamp
+	(*structpb.Value)(nil),        // 30: google.protobuf.Value
+	(*structpb.Struct)(nil),       // 31: google.protobuf.Struct
 }
 var file_agent_proto_depIdxs = []int32{
 	6,  // 0: agent.SelectStackResult.summary:type_name -> agent.StackSummary
 	6,  // 1: agent.InfoResult.summary:type_name -> agent.StackSummary
-	30, // 2: agent.StackSummary.last_update:type_name -> google.protobuf.Timestamp
-	28, // 3: agent.SetAllConfigRequest.config:type_name -> agent.SetAllConfigRequest.ConfigEntry
-	31, // 4: agent.ConfigValue.value:type_name -> google.protobuf.Value
-	9,  // 5: agent.ConfigValue.value_from:type_name -> agent.ConfigValueFrom
-	32, // 6: agent.RefreshStream.event:type_name -> google.protobuf.Struct
+	29, // 2: agent.StackSummary.last_update:type_name -> google.protobuf.Timestamp
+	8,  // 3: agent.SetAllConfigRequest.config:type_name -> agent.ConfigItem
+	30, // 4: agent.ConfigItem.value:type_name -> google.protobuf.Value
+	9,  // 5: agent.ConfigItem.value_from:type_name -> agent.ConfigValueFrom
+	31, // 6: agent.RefreshStream.event:type_name -> google.protobuf.Struct
 	15, // 7: agent.RefreshStream.result:type_name -> agent.RefreshResult
 	24, // 8: agent.RefreshResult.summary:type_name -> agent.UpdateSummary
 	17, // 9: agent.PreviewRequest.policy_pack:type_name -> agent.PolicyPack
-	32, // 10: agent.PreviewStream.event:type_name -> google.protobuf.Struct
+	31, // 10: agent.PreviewStream.event:type_name -> google.protobuf.Struct
 	19, // 11: agent.PreviewStream.result:type_name -> agent.PreviewResult
 	24, // 12: agent.PreviewResult.summary:type_name -> agent.UpdateSummary
 	17, // 13: agent.UpRequest.policy_pack:type_name -> agent.PolicyPack
-	32, // 14: agent.UpStream.event:type_name -> google.protobuf.Struct
+	31, // 14: agent.UpStream.event:type_name -> google.protobuf.Struct
 	22, // 15: agent.UpStream.result:type_name -> agent.UpResult
 	24, // 16: agent.UpResult.summary:type_name -> agent.UpdateSummary
-	29, // 17: agent.UpResult.outputs:type_name -> agent.UpResult.OutputsEntry
-	30, // 18: agent.UpdateSummary.start_time:type_name -> google.protobuf.Timestamp
-	30, // 19: agent.UpdateSummary.end_time:type_name -> google.protobuf.Timestamp
-	32, // 20: agent.DestroyStream.event:type_name -> google.protobuf.Struct
+	28, // 17: agent.UpResult.outputs:type_name -> agent.UpResult.OutputsEntry
+	29, // 18: agent.UpdateSummary.start_time:type_name -> google.protobuf.Timestamp
+	29, // 19: agent.UpdateSummary.end_time:type_name -> google.protobuf.Timestamp
+	31, // 20: agent.DestroyStream.event:type_name -> google.protobuf.Struct
 	27, // 21: agent.DestroyStream.result:type_name -> agent.DestroyResult
 	24, // 22: agent.DestroyResult.summary:type_name -> agent.UpdateSummary
-	8,  // 23: agent.SetAllConfigRequest.ConfigEntry.value:type_name -> agent.ConfigValue
-	23, // 24: agent.UpResult.OutputsEntry.value:type_name -> agent.OutputValue
-	0,  // 25: agent.AutomationService.WhoAmI:input_type -> agent.WhoAmIRequest
-	2,  // 26: agent.AutomationService.SelectStack:input_type -> agent.SelectStackRequest
-	4,  // 27: agent.AutomationService.Info:input_type -> agent.InfoRequest
-	7,  // 28: agent.AutomationService.SetAllConfig:input_type -> agent.SetAllConfigRequest
-	11, // 29: agent.AutomationService.Install:input_type -> agent.InstallRequest
-	16, // 30: agent.AutomationService.Preview:input_type -> agent.PreviewRequest
-	13, // 31: agent.AutomationService.Refresh:input_type -> agent.RefreshRequest
-	20, // 32: agent.AutomationService.Up:input_type -> agent.UpRequest
-	25, // 33: agent.AutomationService.Destroy:input_type -> agent.DestroyRequest
-	1,  // 34: agent.AutomationService.WhoAmI:output_type -> agent.WhoAmIResult
-	3,  // 35: agent.AutomationService.SelectStack:output_type -> agent.SelectStackResult
-	5,  // 36: agent.AutomationService.Info:output_type -> agent.InfoResult
-	10, // 37: agent.AutomationService.SetAllConfig:output_type -> agent.SetAllConfigResult
-	12, // 38: agent.AutomationService.Install:output_type -> agent.InstallResult
-	18, // 39: agent.AutomationService.Preview:output_type -> agent.PreviewStream
-	14, // 40: agent.AutomationService.Refresh:output_type -> agent.RefreshStream
-	21, // 41: agent.AutomationService.Up:output_type -> agent.UpStream
-	26, // 42: agent.AutomationService.Destroy:output_type -> agent.DestroyStream
-	34, // [34:43] is the sub-list for method output_type
-	25, // [25:34] is the sub-list for method input_type
-	25, // [25:25] is the sub-list for extension type_name
-	25, // [25:25] is the sub-list for extension extendee
-	0,  // [0:25] is the sub-list for field type_name
+	23, // 23: agent.UpResult.OutputsEntry.value:type_name -> agent.OutputValue
+	0,  // 24: agent.AutomationService.WhoAmI:input_type -> agent.WhoAmIRequest
+	2,  // 25: agent.AutomationService.SelectStack:input_type -> agent.SelectStackRequest
+	4,  // 26: agent.AutomationService.Info:input_type -> agent.InfoRequest
+	7,  // 27: agent.AutomationService.SetAllConfig:input_type -> agent.SetAllConfigRequest
+	11, // 28: agent.AutomationService.Install:input_type -> agent.InstallRequest
+	16, // 29: agent.AutomationService.Preview:input_type -> agent.PreviewRequest
+	13, // 30: agent.AutomationService.Refresh:input_type -> agent.RefreshRequest
+	20, // 31: agent.AutomationService.Up:input_type -> agent.UpRequest
+	25, // 32: agent.AutomationService.Destroy:input_type -> agent.DestroyRequest
+	1,  // 33: agent.AutomationService.WhoAmI:output_type -> agent.WhoAmIResult
+	3,  // 34: agent.AutomationService.SelectStack:output_type -> agent.SelectStackResult
+	5,  // 35: agent.AutomationService.Info:output_type -> agent.InfoResult
+	10, // 36: agent.AutomationService.SetAllConfig:output_type -> agent.SetAllConfigResult
+	12, // 37: agent.AutomationService.Install:output_type -> agent.InstallResult
+	18, // 38: agent.AutomationService.Preview:output_type -> agent.PreviewStream
+	14, // 39: agent.AutomationService.Refresh:output_type -> agent.RefreshStream
+	21, // 40: agent.AutomationService.Up:output_type -> agent.UpStream
+	26, // 41: agent.AutomationService.Destroy:output_type -> agent.DestroyStream
+	33, // [33:42] is the sub-list for method output_type
+	24, // [24:33] is the sub-list for method input_type
+	24, // [24:24] is the sub-list for extension type_name
+	24, // [24:24] is the sub-list for extension extendee
+	0,  // [0:24] is the sub-list for field type_name
 }
 
 func init() { file_agent_proto_init() }
@@ -2465,7 +2466,7 @@ func file_agent_proto_init() {
 			}
 		}
 		file_agent_proto_msgTypes[8].Exporter = func(v any, i int) any {
-			switch v := v.(*ConfigValue); i {
+			switch v := v.(*ConfigItem); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2707,10 +2708,9 @@ func file_agent_proto_init() {
 	}
 	file_agent_proto_msgTypes[2].OneofWrappers = []any{}
 	file_agent_proto_msgTypes[6].OneofWrappers = []any{}
-	file_agent_proto_msgTypes[7].OneofWrappers = []any{}
 	file_agent_proto_msgTypes[8].OneofWrappers = []any{
-		(*ConfigValue_Value)(nil),
-		(*ConfigValue_ValueFrom)(nil),
+		(*ConfigItem_Value)(nil),
+		(*ConfigItem_ValueFrom)(nil),
 	}
 	file_agent_proto_msgTypes[9].OneofWrappers = []any{
 		(*ConfigValueFrom_Env)(nil),
@@ -2746,7 +2746,7 @@ func file_agent_proto_init() {
 			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
 			RawDescriptor: file_agent_proto_rawDesc,
 			NumEnums:      0,
-			NumMessages:   30,
+			NumMessages:   29,
 			NumExtensions: 0,
 			NumServices:   1,
 		},
diff --git a/agent/pkg/proto/agent.proto b/agent/pkg/proto/agent.proto
index c733c0dc..0f5cb793 100644
--- a/agent/pkg/proto/agent.proto
+++ b/agent/pkg/proto/agent.proto
@@ -91,24 +91,23 @@ message StackSummary {
 }
 
 message SetAllConfigRequest {
-  optional bool path =
-      1; // Parse the keys as paths in a map or list rather than raw strings
-  map<string, ConfigValue> config =
-      2; // a map of ConfigValue used by Pulumi programs
+  repeated ConfigItem config = 1;
 }
 
-message ConfigValue {
+message ConfigItem {
+  string key = 1; // The config's key.
+  optional bool path = 2; // Parse the key as a paths in a map or list rather than as a raw string.
   oneof v {
-    google.protobuf.Value value = 1;
-    ConfigValueFrom value_from = 2;
+    google.protobuf.Value value = 3; // A literal value.
+    ConfigValueFrom value_from = 4; // A value read from the environment or local disk.
   }
-  optional bool secret = 3;
+  optional bool secret = 5; // Whether the config is a secret.
 }
 
 message ConfigValueFrom {
   oneof f {
-    string env = 1;  // the name of an environment variable to read
-    string path = 2; // the path to a file to read
+    string env = 1;  // The name of an environment variable to read>
+    string path = 2; // The path to a file to read.
   }
 }
 
diff --git a/agent/pkg/server/grpc_test.go b/agent/pkg/server/grpc_test.go
index 263719b1..b7e847aa 100644
--- a/agent/pkg/server/grpc_test.go
+++ b/agent/pkg/server/grpc_test.go
@@ -13,9 +13,7 @@ WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 See the License for the specific language governing permissions and
 limitations under the License.
 */
-package server_test
-
-// TODO: Why are we using a black box test package?
+package server
 
 import (
 	"context"
@@ -25,7 +23,6 @@ import (
 	"time"
 
 	pb "github.com/pulumi/pulumi-kubernetes-operator/v2/agent/pkg/proto"
-	"github.com/pulumi/pulumi-kubernetes-operator/v2/agent/pkg/server"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"go.uber.org/zap"
@@ -45,7 +42,7 @@ func TestGracefulShutdown(t *testing.T) {
 	tc := newTC(ctx, t, tcOptions{ProjectDir: "./testdata/hang", Stacks: []string{"test"}})
 	log := zap.L().Named("test").Sugar()
 	lis := bufconn.Listen(1024)
-	s := server.NewGRPC(log, tc.server, nil)
+	s := NewGRPC(log, tc.server, nil)
 	go func() {
 		// This should exit cleanly if we shut down gracefully.
 		if err := s.Serve(ctx, lis); err != nil {
diff --git a/agent/pkg/server/server.go b/agent/pkg/server/server.go
index 3b60a370..07e7b90e 100644
--- a/agent/pkg/server/server.go
+++ b/agent/pkg/server/server.go
@@ -20,6 +20,7 @@ import (
 	"encoding/json"
 	"fmt"
 	"os"
+	"strings"
 	"sync"
 	"sync/atomic"
 	"time"
@@ -41,6 +42,8 @@ import (
 	"github.com/pulumi/pulumi/sdk/v3/go/auto/optrefresh"
 	"github.com/pulumi/pulumi/sdk/v3/go/auto/optup"
 	"github.com/pulumi/pulumi/sdk/v3/go/common/apitype"
+	"github.com/pulumi/pulumi/sdk/v3/go/common/resource/config"
+	"github.com/pulumi/pulumi/sdk/v3/go/common/tokens"
 )
 
 const (
@@ -242,27 +245,67 @@ func (s *Server) SetAllConfig(ctx context.Context, in *pb.SetAllConfigRequest) (
 		return nil, err
 	}
 
-	config := make(map[string]auto.ConfigValue)
-	for k, inv := range in.GetConfig() {
-		if k == "" {
-			return nil, status.Errorf(codes.InvalidArgument, "invalid config key: %s", k)
-		}
-		v, err := unmarshalConfigValue(inv)
-		if err != nil {
-			return nil, err
-		}
-		config[k] = v
+	p, err := stack.Workspace().ProjectSettings(ctx)
+	if err != nil {
+		return nil, fmt.Errorf("getting project settings: %w", err)
+	}
+
+	config, err := unmarshalConfigItems(p.Name.String(), in.Config)
+	if err != nil {
+		return nil, fmt.Errorf("config items: %w", err)
 	}
+
 	s.log.Debugw("setting all config", "config", config)
 
-	err = stack.SetAllConfigWithOptions(ctx, config, &auto.ConfigOptions{
-		Path: in.GetPath(),
-	})
+	err = stack.SetAllConfigWithOptions(ctx, config, &auto.ConfigOptions{Path: true})
 	if err != nil {
 		return nil, err
 	}
 
-	return nil, nil
+	return &pb.SetAllConfigResult{}, nil
+}
+
+// unmarshalConfigItems maps proto ConfigItems to an auto.ConfigMap whose
+// structure is appropriate for invoking with `pulumi config set-all --path`
+// for efficiency. Config items whose keys are not meant to be treated as paths
+// are escaped so they are treated as verbatim property paths.
+func unmarshalConfigItems(project string, items []*pb.ConfigItem) (auto.ConfigMap, error) {
+	out := auto.ConfigMap{}
+
+	for _, item := range items {
+		v, err := unmarshalConfigItem(item) // Resolves valueFrom.
+		if err != nil {
+			return nil, fmt.Errorf("unmarshalling %q config: %w", item.Key, err)
+		}
+
+		// ParseKey requires all keys to be explicitly namespaced, so scope any
+		// implicit keys to our project.
+		key := item.Key
+		if !strings.Contains(key, tokens.TokenDelimiter) {
+			key = project + ":" + key
+		}
+		k, err := config.ParseKey(key)
+		if err != nil {
+			return nil, fmt.Errorf("parsing %q key: %w", key, err)
+		}
+
+		// Keys which are not meant to be interpreted as paths as escaped so
+		// subsequent path parsing treats them as-is. In particular "foo"
+		// becomes `["<foo>"]`. Items which are already escaped in this way are
+		// untouched. See
+		// https://github.com/pulumi/pulumi/blob/4424d69177c47385ea4a01d8ad1b0b825d394f63/sdk/go/common/resource/properties_path.go#L32-L64
+		path := false
+		if item.Path != nil {
+			path = *item.Path
+		}
+		if !path && !(strings.HasPrefix(k.Name(), `["`) && strings.HasSuffix(k.Name(), `"]`)) {
+			k = config.MustMakeKey(k.Namespace(), fmt.Sprintf("[%q]", k.Name()))
+		}
+
+		out[k.String()] = v
+	}
+
+	return out, nil
 }
 
 func (s *Server) Install(ctx context.Context, in *pb.InstallRequest) (*pb.InstallResult, error) {
@@ -656,15 +699,15 @@ func (s *Server) Destroy(in *pb.DestroyRequest, srv pb.AutomationService_Destroy
 	return nil
 }
 
-func unmarshalConfigValue(inv *pb.ConfigValue) (auto.ConfigValue, error) {
+func unmarshalConfigItem(inv *pb.ConfigItem) (auto.ConfigValue, error) {
 	v := auto.ConfigValue{
 		Secret: inv.GetSecret(),
 	}
 	switch vv := inv.V.(type) {
-	case *pb.ConfigValue_Value:
+	case *pb.ConfigItem_Value:
 		// FUTURE: use JSON values
 		v.Value = fmt.Sprintf("%v", vv.Value.AsInterface())
-	case *pb.ConfigValue_ValueFrom:
+	case *pb.ConfigItem_ValueFrom:
 		switch from := vv.ValueFrom.F.(type) {
 		case *pb.ConfigValueFrom_Env:
 			data, ok := os.LookupEnv(from.Env)
diff --git a/agent/pkg/server/server_test.go b/agent/pkg/server/server_test.go
index b67c238f..87ba8c26 100644
--- a/agent/pkg/server/server_test.go
+++ b/agent/pkg/server/server_test.go
@@ -1,4 +1,4 @@
-package server_test
+package server
 
 import (
 	"context"
@@ -13,13 +13,16 @@ import (
 	"github.com/onsi/gomega"
 	"github.com/onsi/gomega/format"
 	"github.com/onsi/gomega/types"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 	"google.golang.org/grpc"
 	"google.golang.org/grpc/codes"
 	"google.golang.org/grpc/status"
 	"google.golang.org/protobuf/types/known/structpb"
+	"k8s.io/utils/ptr"
 
 	pb "github.com/pulumi/pulumi-kubernetes-operator/v2/agent/pkg/proto"
-	"github.com/pulumi/pulumi-kubernetes-operator/v2/agent/pkg/server"
+
 	"github.com/pulumi/pulumi/sdk/v3/go/auto"
 	"github.com/pulumi/pulumi/sdk/v3/go/common/util/fsutil"
 	"github.com/pulumi/pulumi/sdk/v3/go/common/workspace"
@@ -35,7 +38,7 @@ func TestNewServer(t *testing.T) {
 	tests := []struct {
 		name       string
 		projectDir string
-		opts       *server.Options
+		opts       *Options
 		wantErr    any
 	}{
 		{
@@ -54,7 +57,7 @@ func TestNewServer(t *testing.T) {
 		{
 			name:       "new stack",
 			projectDir: "./testdata/simple",
-			opts:       &server.Options{StackName: "new"},
+			opts:       &Options{StackName: "new"},
 		},
 	}
 	for _, tt := range tests {
@@ -66,7 +69,7 @@ func TestNewServer(t *testing.T) {
 			ctx := newContext(t)
 			ws := newWorkspace(ctx, t, tt.projectDir)
 
-			_, err := server.NewServer(ctx, ws, tt.opts)
+			_, err := NewServer(ctx, ws, tt.opts)
 			if tt.wantErr != nil {
 				g.Expect(err).To(gomega.MatchError(tt.wantErr))
 			} else {
@@ -162,7 +165,7 @@ func TestSelectStack(t *testing.T) {
 			name: "non-existent stack with create",
 			req: pb.SelectStackRequest{
 				StackName: "one",
-				Create:    Pointer(true),
+				Create:    ptr.To(true),
 			},
 		},
 	}
@@ -246,23 +249,24 @@ func TestSetAllConfig(t *testing.T) {
 	tests := []struct {
 		name    string
 		stacks  []string
-		req     pb.SetAllConfigRequest
-		wantErr any
+		req     *pb.SetAllConfigRequest
+		wantErr error
 		want    auto.ConfigMap
 	}{
 		{
 			name:    "no active stack",
 			stacks:  []string{},
-			req:     pb.SetAllConfigRequest{},
+			req:     &pb.SetAllConfigRequest{},
 			wantErr: status.Error(codes.FailedPrecondition, "no stack is selected"),
 		},
 		{
 			name:   "literal",
 			stacks: []string{TestStackName},
-			req: pb.SetAllConfigRequest{
-				Config: map[string]*pb.ConfigValue{
-					"foo": {V: &pb.ConfigValue_Value{Value: strVal}},
-				},
+			req: &pb.SetAllConfigRequest{
+				Config: []*pb.ConfigItem{{
+					Key: "foo",
+					V:   &pb.ConfigItem_Value{Value: strVal},
+				}},
 			},
 			want: auto.ConfigMap{
 				"simple:foo": {Value: "bar"},
@@ -271,11 +275,12 @@ func TestSetAllConfig(t *testing.T) {
 		{
 			name:   "env",
 			stacks: []string{TestStackName},
-			req: pb.SetAllConfigRequest{
+			req: &pb.SetAllConfigRequest{
 				// note that TestMain sets the FOO environment variable to a test value
-				Config: map[string]*pb.ConfigValue{
-					"foo": {V: &pb.ConfigValue_ValueFrom{ValueFrom: &pb.ConfigValueFrom{F: &pb.ConfigValueFrom_Env{Env: "FOO"}}}},
-				},
+				Config: []*pb.ConfigItem{{
+					Key: "foo",
+					V:   &pb.ConfigItem_ValueFrom{ValueFrom: &pb.ConfigValueFrom{F: &pb.ConfigValueFrom_Env{Env: "FOO"}}},
+				}},
 			},
 			want: auto.ConfigMap{
 				"simple:foo": {Value: "bar"},
@@ -284,11 +289,12 @@ func TestSetAllConfig(t *testing.T) {
 		{
 			name:   "file",
 			stacks: []string{TestStackName},
-			req: pb.SetAllConfigRequest{
+			req: &pb.SetAllConfigRequest{
 				// note that TestMain sets the FOO environment variable to a test value
-				Config: map[string]*pb.ConfigValue{
-					"foo": {V: &pb.ConfigValue_ValueFrom{ValueFrom: &pb.ConfigValueFrom{F: &pb.ConfigValueFrom_Path{Path: "./testdata/foo.txt"}}}},
-				},
+				Config: []*pb.ConfigItem{{
+					Key: "foo",
+					V:   &pb.ConfigItem_ValueFrom{ValueFrom: &pb.ConfigValueFrom{F: &pb.ConfigValueFrom_Path{Path: "./testdata/foo.txt"}}},
+				}},
 			},
 			want: auto.ConfigMap{
 				"simple:foo": {Value: "bar"},
@@ -297,10 +303,13 @@ func TestSetAllConfig(t *testing.T) {
 		{
 			name:   "path-based",
 			stacks: []string{TestStackName},
-			req: pb.SetAllConfigRequest{
-				Path: Pointer(true),
-				Config: map[string]*pb.ConfigValue{
-					"a.b": {V: &pb.ConfigValue_Value{Value: strVal}},
+			req: &pb.SetAllConfigRequest{
+				Config: []*pb.ConfigItem{
+					{
+						Key:  "a.b",
+						Path: ptr.To(true),
+						V:    &pb.ConfigItem_Value{Value: strVal},
+					},
 				},
 			},
 			want: auto.ConfigMap{
@@ -308,13 +317,75 @@ func TestSetAllConfig(t *testing.T) {
 			},
 		},
 		{
-			name:   "secret",
+			name:   "path-like",
 			stacks: []string{TestStackName},
-			req: pb.SetAllConfigRequest{
-				Config: map[string]*pb.ConfigValue{
-					"foo": {V: &pb.ConfigValue_Value{Value: strVal}, Secret: Pointer(true)},
+			req: &pb.SetAllConfigRequest{
+				Config: []*pb.ConfigItem{
+					{
+						Key:  "a.b",
+						Path: ptr.To(false),
+						V:    &pb.ConfigItem_Value{Value: strVal},
+					}, {
+						Key:  `"quoted[key]"`,
+						Path: ptr.To(false),
+						V:    &pb.ConfigItem_Value{Value: strVal},
+					}, {
+						Key:  `["already.escaped"]`,
+						Path: ptr.To(false),
+						V:    &pb.ConfigItem_Value{Value: strVal},
+					},
 				},
 			},
+			want: auto.ConfigMap{
+				"simple:a.b":             {Value: "bar"},
+				`simple:"quoted[key]"`:   {Value: "bar"},
+				`simple:already.escaped`: {Value: "bar"},
+			},
+		},
+		{
+			name:   "path-overlay",
+			stacks: []string{"nested"},
+			req: &pb.SetAllConfigRequest{
+				Config: []*pb.ConfigItem{
+					{
+						Key:  "myList[0]",
+						Path: ptr.To(true),
+						V:    &pb.ConfigItem_Value{Value: structpb.NewStringValue("1")},
+					},
+					{
+						Key:  "myList[1]",
+						Path: ptr.To(true),
+						V:    &pb.ConfigItem_Value{Value: structpb.NewStringValue("2")},
+					},
+					{
+						Key:  "myList[3]",
+						Path: ptr.To(true),
+						V:    &pb.ConfigItem_Value{Value: structpb.NewStringValue("four")},
+					},
+					{
+						Key:  "outer.more.inner",
+						Path: ptr.To(true),
+						V:    &pb.ConfigItem_Value{Value: structpb.NewStringValue("wrapped")},
+					},
+				},
+			},
+			want: auto.ConfigMap{
+				"aws:region":    {Value: `us-west-2`},
+				"simple:foo":    {Value: `aha`},
+				"simple:bar":    {Value: `1234`},
+				"simple:myList": {Value: `[1,2,"three","four"]`},
+				"simple:outer":  {Value: `{"inner":"my_value","more":{"inner":"wrapped"},"other":"something_else"}`},
+			},
+		},
+		{
+			name:   "secret",
+			stacks: []string{TestStackName},
+			req: &pb.SetAllConfigRequest{
+				Config: []*pb.ConfigItem{{
+					Key: "foo",
+					V:   &pb.ConfigItem_Value{Value: strVal}, Secret: ptr.To(true),
+				}},
+			},
 			want: auto.ConfigMap{
 				"simple:foo": {Value: "bar", Secret: true},
 			},
@@ -322,10 +393,11 @@ func TestSetAllConfig(t *testing.T) {
 		{
 			name:   "typed",
 			stacks: []string{TestStackName},
-			req: pb.SetAllConfigRequest{
-				Config: map[string]*pb.ConfigValue{
-					"enabled": {V: &pb.ConfigValue_Value{Value: boolVal}},
-				},
+			req: &pb.SetAllConfigRequest{
+				Config: []*pb.ConfigItem{{
+					Key: "enabled",
+					V:   &pb.ConfigItem_Value{Value: boolVal},
+				}},
 			},
 			want: auto.ConfigMap{
 				"simple:enabled": {Value: "true"},
@@ -333,22 +405,20 @@ func TestSetAllConfig(t *testing.T) {
 		},
 	}
 	for _, tt := range tests {
-		tt := tt
 		t.Run(tt.name, func(t *testing.T) {
 			t.Parallel()
-			g := gomega.NewWithT(t)
 			ctx := newContext(t)
 			tc := newTC(ctx, t, tcOptions{ProjectDir: "./testdata/simple", Stacks: tt.stacks})
-			_, err := tc.server.SetAllConfig(ctx, &tt.req)
+			_, err := tc.server.SetAllConfig(ctx, tt.req)
 			if tt.wantErr != nil {
-				g.Expect(err).To(gomega.MatchError(tt.wantErr))
-			} else {
-				g.Expect(err).ToNot(gomega.HaveOccurred())
-
-				actual, err := tc.ws.GetAllConfig(ctx, tc.stack.Name())
-				g.Expect(err).ToNot(gomega.HaveOccurred())
-				g.Expect(actual).To(gomega.Equal(tt.want))
+				assert.ErrorIs(t, err, tt.wantErr)
+				return
 			}
+			require.NoError(t, err)
+
+			actual, err := tc.ws.GetAllConfig(ctx, tc.stack.Name())
+			assert.NoError(t, err)
+			assert.Equal(t, tt.want, actual)
 		})
 	}
 }
@@ -457,6 +527,7 @@ var _ pb.AutomationService_UpServer = (*upStream)(nil)
 func (m *upStream) Context() context.Context {
 	return m.ctx
 }
+
 func (m *upStream) Send(resp *pb.UpStream) error {
 	m.mu.Lock()
 	defer m.mu.Unlock()
@@ -531,6 +602,7 @@ var _ pb.AutomationService_PreviewServer = (*previewStream)(nil)
 func (m *previewStream) Context() context.Context {
 	return m.ctx
 }
+
 func (m *previewStream) Send(resp *pb.PreviewStream) error {
 	m.mu.Lock()
 	defer m.mu.Unlock()
@@ -607,6 +679,7 @@ var _ pb.AutomationService_RefreshServer = (*refreshStream)(nil)
 func (m *refreshStream) Context() context.Context {
 	return m.ctx
 }
+
 func (m *refreshStream) Send(resp *pb.RefreshStream) error {
 	m.mu.Lock()
 	defer m.mu.Unlock()
@@ -683,6 +756,7 @@ var _ pb.AutomationService_DestroyServer = (*destroyStream)(nil)
 func (m *destroyStream) Context() context.Context {
 	return m.ctx
 }
+
 func (m *destroyStream) Send(resp *pb.DestroyStream) error {
 	m.mu.Lock()
 	defer m.mu.Unlock()
@@ -711,7 +785,7 @@ func newWorkspace(ctx context.Context, t *testing.T, templateDir string) auto.Wo
 	// generate a project based on the template, with a file backend
 	tempDir := t.TempDir()
 	if templateDir != "" {
-		err := os.MkdirAll(filepath.Join(tempDir, ".pulumi"), 0755)
+		err := os.MkdirAll(filepath.Join(tempDir, ".pulumi"), 0o755)
 		if err != nil {
 			t.Fatalf("failed to create state backend directory: %v", err)
 		}
@@ -741,10 +815,6 @@ func newWorkspace(ctx context.Context, t *testing.T, templateDir string) auto.Wo
 	return ws
 }
 
-func Pointer[T any](d T) *T {
-	return &d
-}
-
 func HasStatusCode(code codes.Code, msg types.GomegaMatcher) types.GomegaMatcher {
 	return gomega.WithTransform(func(err error) status.Status {
 		s, _ := status.FromError(err)
@@ -758,21 +828,21 @@ func HasStatusCode(code codes.Code, msg types.GomegaMatcher) types.GomegaMatcher
 type testContext struct {
 	ws     auto.Workspace
 	stack  *auto.Stack
-	server *server.Server
+	server *Server
 }
 
 type tcOptions struct {
 	ProjectDir string
 	Stacks     []string // pre-create some stacks; last one will be selected
-	ServerOpts *server.Options
+	ServerOpts *Options
 }
 
 func newTC(ctx context.Context, t *testing.T, opts tcOptions) *testContext {
 	ws := newWorkspace(ctx, t, opts.ProjectDir)
 	if opts.ServerOpts == nil {
-		opts.ServerOpts = &server.Options{}
+		opts.ServerOpts = &Options{}
 	}
-	server, err := server.NewServer(ctx, ws, opts.ServerOpts)
+	server, err := NewServer(ctx, ws, opts.ServerOpts)
 	if err != nil {
 		t.Fatalf("failed to create server: %v", err)
 	}
diff --git a/agent/pkg/server/testdata/simple/Pulumi.nested.yaml b/agent/pkg/server/testdata/simple/Pulumi.nested.yaml
new file mode 100644
index 00000000..9f008501
--- /dev/null
+++ b/agent/pkg/server/testdata/simple/Pulumi.nested.yaml
@@ -0,0 +1,11 @@
+config:
+  aws:region: us-west-2
+  simple:bar: 1234
+  simple:foo: aha
+  simple:myList:
+    - one
+    - two
+    - three
+  simple:outer:
+    inner: my_value
+    other: something_else
diff --git a/operator/internal/controller/auto/utils.go b/operator/internal/controller/auto/utils.go
index 4aa06f53..d29a93a5 100644
--- a/operator/internal/controller/auto/utils.go
+++ b/operator/internal/controller/auto/utils.go
@@ -62,15 +62,18 @@ func connect(ctx context.Context, addr string) (*grpc.ClientConn, error) {
 	}
 }
 
-func marshalConfigValue(item autov1alpha1.ConfigItem) *agentpb.ConfigValue {
-	v := &agentpb.ConfigValue{
+func marshalConfigItem(item autov1alpha1.ConfigItem) *agentpb.ConfigItem {
+	v := &agentpb.ConfigItem{
+		Key:    item.Key,
+		Path:   item.Path,
 		Secret: item.Secret,
 	}
 	if item.Value != nil {
-		v.V = &agentpb.ConfigValue_Value{
+		v.V = &agentpb.ConfigItem_Value{
 			Value: structpb.NewStringValue(*item.Value),
 		}
-	} else if item.ValueFrom != nil {
+	}
+	if item.ValueFrom != nil {
 		f := &agentpb.ConfigValueFrom{}
 		if item.ValueFrom.Env != "" {
 			f.F = &agentpb.ConfigValueFrom_Env{
@@ -81,7 +84,7 @@ func marshalConfigValue(item autov1alpha1.ConfigItem) *agentpb.ConfigValue {
 				Path: item.ValueFrom.Path,
 			}
 		}
-		v.V = &agentpb.ConfigValue_ValueFrom{
+		v.V = &agentpb.ConfigItem_ValueFrom{
 			ValueFrom: f,
 		}
 	}
diff --git a/operator/internal/controller/auto/workspace_controller.go b/operator/internal/controller/auto/workspace_controller.go
index af9a63be..f9b0d8ea 100644
--- a/operator/internal/controller/auto/workspace_controller.go
+++ b/operator/internal/controller/auto/workspace_controller.go
@@ -270,19 +270,20 @@ func (r *WorkspaceReconciler) Reconcile(ctx context.Context, req ctrl.Request) (
 				}); err != nil {
 					return err
 				}
+
+				if len(stack.Config) == 0 {
+					l.V(1).Info("No stack configuration to set")
+					return nil
+				}
+
 				l.V(1).Info("Setting the stack configuration")
+
+				config := make([]*agentpb.ConfigItem, 0, len(stack.Config))
 				for _, item := range stack.Config {
-					v := marshalConfigValue(item)
-					if _, err = wc.SetAllConfig(ctx, &agentpb.SetAllConfigRequest{
-						Path: item.Path,
-						Config: map[string]*agentpb.ConfigValue{
-							item.Key: v,
-						},
-					}); err != nil {
-						return err
-					}
+					config = append(config, marshalConfigItem(item))
 				}
-				return nil
+				_, err = wc.SetAllConfig(ctx, &agentpb.SetAllConfigRequest{Config: config})
+				return err
 			}()
 			if err != nil {
 				l.Error(err, "unable to initialize the Pulumi stack")