diff --git a/components/registry-facade/pkg/handover/handover.go b/components/registry-facade/pkg/handover/handover.go
index eccdd0ada64ae2..af2896078b130a 100644
--- a/components/registry-facade/pkg/handover/handover.go
+++ b/components/registry-facade/pkg/handover/handover.go
@@ -1,3 +1,7 @@
+// Copyright (c) 2021 Gitpod GmbH. All rights reserved.
+// Licensed under the GNU Affero General Public License (AGPL).
+// See License-AGPL.txt in the project root for license information.
+
 package handover
 
 import (
diff --git a/components/registry-facade/pkg/handover/handover_test.go b/components/registry-facade/pkg/handover/handover_test.go
index 58c2e75f3aa8b4..7544525df8022c 100644
--- a/components/registry-facade/pkg/handover/handover_test.go
+++ b/components/registry-facade/pkg/handover/handover_test.go
@@ -1,3 +1,7 @@
+// Copyright (c) 2021 Gitpod GmbH. All rights reserved.
+// Licensed under the GNU Affero General Public License (AGPL).
+// See License-AGPL.txt in the project root for license information.
+
 package handover_test
 
 import (
diff --git a/components/supervisor-api/go/info.pb.gw.go b/components/supervisor-api/go/info.pb.gw.go
index f36f9ed5438ba3..ea1385211580c9 100644
--- a/components/supervisor-api/go/info.pb.gw.go
+++ b/components/supervisor-api/go/info.pb.gw.go
@@ -1,4 +1,4 @@
-// Copyright (c) 2020 Gitpod GmbH. All rights reserved.
+// Copyright (c) 2021 Gitpod GmbH. All rights reserved.
 // Licensed under the GNU Affero General Public License (AGPL).
 // See License-AGPL.txt in the project root for license information.
 
diff --git a/components/supervisor-api/go/status.pb.gw.go b/components/supervisor-api/go/status.pb.gw.go
index 3447559ba7e908..3f84ec67fe4859 100644
--- a/components/supervisor-api/go/status.pb.gw.go
+++ b/components/supervisor-api/go/status.pb.gw.go
@@ -1,4 +1,4 @@
-// Copyright (c) 2020 Gitpod GmbH. All rights reserved.
+// Copyright (c) 2021 Gitpod GmbH. All rights reserved.
 // Licensed under the GNU Affero General Public License (AGPL).
 // See License-AGPL.txt in the project root for license information.
 
diff --git a/components/supervisor-api/go/terminal.pb.go b/components/supervisor-api/go/terminal.pb.go
index f262261d4f80ab..21ef45dd742634 100644
--- a/components/supervisor-api/go/terminal.pb.go
+++ b/components/supervisor-api/go/terminal.pb.go
@@ -39,7 +39,9 @@ type OpenTerminalRequest struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	Env map[string]string `protobuf:"bytes,2,rep,name=env,proto3" json:"env,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"`
+	Workdir     string            `protobuf:"bytes,1,opt,name=workdir,proto3" json:"workdir,omitempty"`
+	Env         map[string]string `protobuf:"bytes,2,rep,name=env,proto3" json:"env,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"`
+	Annotations map[string]string `protobuf:"bytes,3,rep,name=annotations,proto3" json:"annotations,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"`
 }
 
 func (x *OpenTerminalRequest) Reset() {
@@ -74,6 +76,13 @@ func (*OpenTerminalRequest) Descriptor() ([]byte, []int) {
 	return file_terminal_proto_rawDescGZIP(), []int{0}
 }
 
+func (x *OpenTerminalRequest) GetWorkdir() string {
+	if x != nil {
+		return x.Workdir
+	}
+	return ""
+}
+
 func (x *OpenTerminalRequest) GetEnv() map[string]string {
 	if x != nil {
 		return x.Env
@@ -81,6 +90,13 @@ func (x *OpenTerminalRequest) GetEnv() map[string]string {
 	return nil
 }
 
+func (x *OpenTerminalRequest) GetAnnotations() map[string]string {
+	if x != nil {
+		return x.Annotations
+	}
+	return nil
+}
+
 type OpenTerminalResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -705,15 +721,19 @@ type ListTerminalsResponse_Terminal struct {
 	sizeCache     protoimpl.SizeCache
 	unknownFields protoimpl.UnknownFields
 
-	Alias   string   `protobuf:"bytes,1,opt,name=alias,proto3" json:"alias,omitempty"`
-	Command []string `protobuf:"bytes,2,rep,name=command,proto3" json:"command,omitempty"`
-	Title   string   `protobuf:"bytes,3,opt,name=title,proto3" json:"title,omitempty"`
+	Alias          string            `protobuf:"bytes,1,opt,name=alias,proto3" json:"alias,omitempty"`
+	Command        []string          `protobuf:"bytes,2,rep,name=command,proto3" json:"command,omitempty"`
+	Title          string            `protobuf:"bytes,3,opt,name=title,proto3" json:"title,omitempty"`
+	Pid            int64             `protobuf:"varint,4,opt,name=pid,proto3" json:"pid,omitempty"`
+	InitialWorkdir string            `protobuf:"bytes,5,opt,name=initial_workdir,json=initialWorkdir,proto3" json:"initial_workdir,omitempty"`
+	CurrentWorkdir string            `protobuf:"bytes,6,opt,name=current_workdir,json=currentWorkdir,proto3" json:"current_workdir,omitempty"`
+	Annotations    map[string]string `protobuf:"bytes,7,rep,name=annotations,proto3" json:"annotations,omitempty" protobuf_key:"bytes,1,opt,name=key,proto3" protobuf_val:"bytes,2,opt,name=value,proto3"`
 }
 
 func (x *ListTerminalsResponse_Terminal) Reset() {
 	*x = ListTerminalsResponse_Terminal{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_terminal_proto_msgTypes[13]
+		mi := &file_terminal_proto_msgTypes[14]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -726,7 +746,7 @@ func (x *ListTerminalsResponse_Terminal) String() string {
 func (*ListTerminalsResponse_Terminal) ProtoMessage() {}
 
 func (x *ListTerminalsResponse_Terminal) ProtoReflect() protoreflect.Message {
-	mi := &file_terminal_proto_msgTypes[13]
+	mi := &file_terminal_proto_msgTypes[14]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -763,116 +783,171 @@ func (x *ListTerminalsResponse_Terminal) GetTitle() string {
 	return ""
 }
 
+func (x *ListTerminalsResponse_Terminal) GetPid() int64 {
+	if x != nil {
+		return x.Pid
+	}
+	return 0
+}
+
+func (x *ListTerminalsResponse_Terminal) GetInitialWorkdir() string {
+	if x != nil {
+		return x.InitialWorkdir
+	}
+	return ""
+}
+
+func (x *ListTerminalsResponse_Terminal) GetCurrentWorkdir() string {
+	if x != nil {
+		return x.CurrentWorkdir
+	}
+	return ""
+}
+
+func (x *ListTerminalsResponse_Terminal) GetAnnotations() map[string]string {
+	if x != nil {
+		return x.Annotations
+	}
+	return nil
+}
+
 var File_terminal_proto protoreflect.FileDescriptor
 
 var file_terminal_proto_rawDesc = []byte{
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-	0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x57, 0x72, 0x69, 0x74, 0x65, 0x54, 0x65,
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 	0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x22,
-	0x82, 0xd3, 0xe4, 0x93, 0x02, 0x1c, 0x22, 0x1a, 0x2f, 0x76, 0x31, 0x2f, 0x74, 0x65, 0x72, 0x6d,
-	0x69, 0x6e, 0x61, 0x6c, 0x2f, 0x77, 0x72, 0x69, 0x74, 0x65, 0x2f, 0x7b, 0x61, 0x6c, 0x69, 0x61,
-	0x73, 0x7d, 0x12, 0x54, 0x0a, 0x07, 0x53, 0x65, 0x74, 0x53, 0x69, 0x7a, 0x65, 0x12, 0x22, 0x2e,
-	0x73, 0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x53, 0x65, 0x74, 0x54, 0x65,
-	0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x53, 0x69, 0x7a, 0x65, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73,
-	0x74, 0x1a, 0x23, 0x2e, 0x73, 0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x53,
-	0x65, 0x74, 0x54, 0x65, 0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x53, 0x69, 0x7a, 0x65, 0x52, 0x65,
-	0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x00, 0x42, 0x07, 0x5a, 0x05, 0x2e, 0x3b, 0x61, 0x70,
-	0x69, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
+	0x82, 0xd3, 0xe4, 0x93, 0x02, 0x1c, 0x12, 0x1a, 0x2f, 0x76, 0x31, 0x2f, 0x74, 0x65, 0x72, 0x6d,
+	0x69, 0x6e, 0x61, 0x6c, 0x2f, 0x63, 0x6c, 0x6f, 0x73, 0x65, 0x2f, 0x7b, 0x61, 0x6c, 0x69, 0x61,
+	0x73, 0x7d, 0x12, 0x66, 0x0a, 0x04, 0x4c, 0x69, 0x73, 0x74, 0x12, 0x20, 0x2e, 0x73, 0x75, 0x70,
+	0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x4c, 0x69, 0x73, 0x74, 0x54, 0x65, 0x72, 0x6d,
+	0x69, 0x6e, 0x61, 0x6c, 0x73, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x21, 0x2e, 0x73,
+	0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x4c, 0x69, 0x73, 0x74, 0x54, 0x65,
+	0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22,
+	0x19, 0x82, 0xd3, 0xe4, 0x93, 0x02, 0x13, 0x12, 0x11, 0x2f, 0x76, 0x31, 0x2f, 0x74, 0x65, 0x72,
+	0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x2f, 0x6c, 0x69, 0x73, 0x74, 0x12, 0x76, 0x0a, 0x06, 0x4c, 0x69,
+	0x73, 0x74, 0x65, 0x6e, 0x12, 0x21, 0x2e, 0x73, 0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f,
+	0x72, 0x2e, 0x4c, 0x69, 0x73, 0x74, 0x65, 0x6e, 0x54, 0x65, 0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c,
+	0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x22, 0x2e, 0x73, 0x75, 0x70, 0x65, 0x72, 0x76,
+	0x69, 0x73, 0x6f, 0x72, 0x2e, 0x4c, 0x69, 0x73, 0x74, 0x65, 0x6e, 0x54, 0x65, 0x72, 0x6d, 0x69,
+	0x6e, 0x61, 0x6c, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x23, 0x82, 0xd3, 0xe4,
+	0x93, 0x02, 0x1d, 0x12, 0x1b, 0x2f, 0x76, 0x31, 0x2f, 0x74, 0x65, 0x72, 0x6d, 0x69, 0x6e, 0x61,
+	0x6c, 0x2f, 0x6c, 0x69, 0x73, 0x74, 0x65, 0x6e, 0x2f, 0x7b, 0x61, 0x6c, 0x69, 0x61, 0x73, 0x7d,
+	0x30, 0x01, 0x12, 0x70, 0x0a, 0x05, 0x57, 0x72, 0x69, 0x74, 0x65, 0x12, 0x20, 0x2e, 0x73, 0x75,
+	0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x57, 0x72, 0x69, 0x74, 0x65, 0x54, 0x65,
+	0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x52, 0x65, 0x71, 0x75, 0x65, 0x73, 0x74, 0x1a, 0x21, 0x2e,
+	0x73, 0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x57, 0x72, 0x69, 0x74, 0x65,
+	0x54, 0x65, 0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65,
+	0x22, 0x22, 0x82, 0xd3, 0xe4, 0x93, 0x02, 0x1c, 0x22, 0x1a, 0x2f, 0x76, 0x31, 0x2f, 0x74, 0x65,
+	0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x2f, 0x77, 0x72, 0x69, 0x74, 0x65, 0x2f, 0x7b, 0x61, 0x6c,
+	0x69, 0x61, 0x73, 0x7d, 0x12, 0x54, 0x0a, 0x07, 0x53, 0x65, 0x74, 0x53, 0x69, 0x7a, 0x65, 0x12,
+	0x22, 0x2e, 0x73, 0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72, 0x2e, 0x53, 0x65, 0x74,
+	0x54, 0x65, 0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x53, 0x69, 0x7a, 0x65, 0x52, 0x65, 0x71, 0x75,
+	0x65, 0x73, 0x74, 0x1a, 0x23, 0x2e, 0x73, 0x75, 0x70, 0x65, 0x72, 0x76, 0x69, 0x73, 0x6f, 0x72,
+	0x2e, 0x53, 0x65, 0x74, 0x54, 0x65, 0x72, 0x6d, 0x69, 0x6e, 0x61, 0x6c, 0x53, 0x69, 0x7a, 0x65,
+	0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x22, 0x00, 0x42, 0x07, 0x5a, 0x05, 0x2e, 0x3b,
+	0x61, 0x70, 0x69, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
@@ -887,7 +962,7 @@ func file_terminal_proto_rawDescGZIP() []byte {
 	return file_terminal_proto_rawDescData
 }
 
-var file_terminal_proto_msgTypes = make([]protoimpl.MessageInfo, 14)
+var file_terminal_proto_msgTypes = make([]protoimpl.MessageInfo, 16)
 var file_terminal_proto_goTypes = []interface{}{
 	(*OpenTerminalRequest)(nil),            // 0: supervisor.OpenTerminalRequest
 	(*OpenTerminalResponse)(nil),           // 1: supervisor.OpenTerminalResponse
@@ -902,28 +977,32 @@ var file_terminal_proto_goTypes = []interface{}{
 	(*SetTerminalSizeRequest)(nil),         // 10: supervisor.SetTerminalSizeRequest
 	(*SetTerminalSizeResponse)(nil),        // 11: supervisor.SetTerminalSizeResponse
 	nil,                                    // 12: supervisor.OpenTerminalRequest.EnvEntry
-	(*ListTerminalsResponse_Terminal)(nil), // 13: supervisor.ListTerminalsResponse.Terminal
+	nil,                                    // 13: supervisor.OpenTerminalRequest.AnnotationsEntry
+	(*ListTerminalsResponse_Terminal)(nil), // 14: supervisor.ListTerminalsResponse.Terminal
+	nil,                                    // 15: supervisor.ListTerminalsResponse.Terminal.AnnotationsEntry
 }
 var file_terminal_proto_depIdxs = []int32{
 	12, // 0: supervisor.OpenTerminalRequest.env:type_name -> supervisor.OpenTerminalRequest.EnvEntry
-	13, // 1: supervisor.ListTerminalsResponse.terminals:type_name -> supervisor.ListTerminalsResponse.Terminal
-	0,  // 2: supervisor.TerminalService.Open:input_type -> supervisor.OpenTerminalRequest
-	2,  // 3: supervisor.TerminalService.Close:input_type -> supervisor.CloseTerminalRequest
-	4,  // 4: supervisor.TerminalService.List:input_type -> supervisor.ListTerminalsRequest
-	6,  // 5: supervisor.TerminalService.Listen:input_type -> supervisor.ListenTerminalRequest
-	8,  // 6: supervisor.TerminalService.Write:input_type -> supervisor.WriteTerminalRequest
-	10, // 7: supervisor.TerminalService.SetSize:input_type -> supervisor.SetTerminalSizeRequest
-	1,  // 8: supervisor.TerminalService.Open:output_type -> supervisor.OpenTerminalResponse
-	3,  // 9: supervisor.TerminalService.Close:output_type -> supervisor.CloseTerminalResponse
-	5,  // 10: supervisor.TerminalService.List:output_type -> supervisor.ListTerminalsResponse
-	7,  // 11: supervisor.TerminalService.Listen:output_type -> supervisor.ListenTerminalResponse
-	9,  // 12: supervisor.TerminalService.Write:output_type -> supervisor.WriteTerminalResponse
-	11, // 13: supervisor.TerminalService.SetSize:output_type -> supervisor.SetTerminalSizeResponse
-	8,  // [8:14] is the sub-list for method output_type
-	2,  // [2:8] is the sub-list for method input_type
-	2,  // [2:2] is the sub-list for extension type_name
-	2,  // [2:2] is the sub-list for extension extendee
-	0,  // [0:2] is the sub-list for field type_name
+	13, // 1: supervisor.OpenTerminalRequest.annotations:type_name -> supervisor.OpenTerminalRequest.AnnotationsEntry
+	14, // 2: supervisor.ListTerminalsResponse.terminals:type_name -> supervisor.ListTerminalsResponse.Terminal
+	15, // 3: supervisor.ListTerminalsResponse.Terminal.annotations:type_name -> supervisor.ListTerminalsResponse.Terminal.AnnotationsEntry
+	0,  // 4: supervisor.TerminalService.Open:input_type -> supervisor.OpenTerminalRequest
+	2,  // 5: supervisor.TerminalService.Close:input_type -> supervisor.CloseTerminalRequest
+	4,  // 6: supervisor.TerminalService.List:input_type -> supervisor.ListTerminalsRequest
+	6,  // 7: supervisor.TerminalService.Listen:input_type -> supervisor.ListenTerminalRequest
+	8,  // 8: supervisor.TerminalService.Write:input_type -> supervisor.WriteTerminalRequest
+	10, // 9: supervisor.TerminalService.SetSize:input_type -> supervisor.SetTerminalSizeRequest
+	1,  // 10: supervisor.TerminalService.Open:output_type -> supervisor.OpenTerminalResponse
+	3,  // 11: supervisor.TerminalService.Close:output_type -> supervisor.CloseTerminalResponse
+	5,  // 12: supervisor.TerminalService.List:output_type -> supervisor.ListTerminalsResponse
+	7,  // 13: supervisor.TerminalService.Listen:output_type -> supervisor.ListenTerminalResponse
+	9,  // 14: supervisor.TerminalService.Write:output_type -> supervisor.WriteTerminalResponse
+	11, // 15: supervisor.TerminalService.SetSize:output_type -> supervisor.SetTerminalSizeResponse
+	10, // [10:16] is the sub-list for method output_type
+	4,  // [4:10] is the sub-list for method input_type
+	4,  // [4:4] is the sub-list for extension type_name
+	4,  // [4:4] is the sub-list for extension extendee
+	0,  // [0:4] is the sub-list for field type_name
 }
 
 func init() { file_terminal_proto_init() }
@@ -1076,7 +1155,7 @@ func file_terminal_proto_init() {
 				return nil
 			}
 		}
-		file_terminal_proto_msgTypes[13].Exporter = func(v interface{}, i int) interface{} {
+		file_terminal_proto_msgTypes[14].Exporter = func(v interface{}, i int) interface{} {
 			switch v := v.(*ListTerminalsResponse_Terminal); i {
 			case 0:
 				return &v.state
@@ -1103,7 +1182,7 @@ func file_terminal_proto_init() {
 			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
 			RawDescriptor: file_terminal_proto_rawDesc,
 			NumEnums:      0,
-			NumMessages:   14,
+			NumMessages:   16,
 			NumExtensions: 0,
 			NumServices:   1,
 		},
diff --git a/components/supervisor-api/go/terminal.pb.gw.go b/components/supervisor-api/go/terminal.pb.gw.go
index 6d199ca059a6b4..fbe4df7a154bc7 100644
--- a/components/supervisor-api/go/terminal.pb.gw.go
+++ b/components/supervisor-api/go/terminal.pb.gw.go
@@ -1,4 +1,4 @@
-// Copyright (c) 2020 Gitpod GmbH. All rights reserved.
+// Copyright (c) 2021 Gitpod GmbH. All rights reserved.
 // Licensed under the GNU Affero General Public License (AGPL).
 // See License-AGPL.txt in the project root for license information.
 
diff --git a/components/supervisor-api/go/token.pb.go b/components/supervisor-api/go/token.pb.go
index 6504552944a26c..b3702ef1c5f164 100644
--- a/components/supervisor-api/go/token.pb.go
+++ b/components/supervisor-api/go/token.pb.go
@@ -167,7 +167,8 @@ type GetTokenResponse struct {
 	unknownFields protoimpl.UnknownFields
 
 	Token string `protobuf:"bytes,1,opt,name=token,proto3" json:"token,omitempty"`
-	User  string `protobuf:"bytes,2,opt,name=user,proto3" json:"user,omitempty"`
+	//* The username of the account associated with the token.
+	User string `protobuf:"bytes,2,opt,name=user,proto3" json:"user,omitempty"`
 }
 
 func (x *GetTokenResponse) Reset() {
diff --git a/components/supervisor-api/go/token.pb.gw.go b/components/supervisor-api/go/token.pb.gw.go
index b69dc1d8b4a638..1830985d303a3d 100644
--- a/components/supervisor-api/go/token.pb.gw.go
+++ b/components/supervisor-api/go/token.pb.gw.go
@@ -1,4 +1,4 @@
-// Copyright (c) 2020 Gitpod GmbH. All rights reserved.
+// Copyright (c) 2021 Gitpod GmbH. All rights reserved.
 // Licensed under the GNU Affero General Public License (AGPL).
 // See License-AGPL.txt in the project root for license information.
 
diff --git a/components/supervisor-api/terminal.proto b/components/supervisor-api/terminal.proto
index 6b68a24ab5c909..8067a534c8db85 100644
--- a/components/supervisor-api/terminal.proto
+++ b/components/supervisor-api/terminal.proto
@@ -48,7 +48,9 @@ service TerminalService {
 }
 
 message OpenTerminalRequest {
+    string workdir = 1;
     map<string, string> env = 2;
+    map<string, string> annotations = 3;
 }
 message OpenTerminalResponse {
     string alias = 1;
@@ -69,6 +71,10 @@ message ListTerminalsResponse {
         string alias = 1;
         repeated string command = 2;
         string title = 3;
+        int64 pid = 4;
+        string initial_workdir = 5;
+        string current_workdir = 6;
+        map<string, string> annotations = 7;
     }
 
     repeated Terminal terminals = 1;
diff --git a/components/supervisor/cmd/terminal-list.go b/components/supervisor/cmd/terminal-list.go
index 1a156ffdea0451..9bea1add261edd 100644
--- a/components/supervisor/cmd/terminal-list.go
+++ b/components/supervisor/cmd/terminal-list.go
@@ -8,6 +8,7 @@ import (
 	"context"
 	"fmt"
 	"os"
+	"sort"
 	"strings"
 	"text/tabwriter"
 	"time"
@@ -34,9 +35,14 @@ var terminalListCmd = &cobra.Command{
 		tw := tabwriter.NewWriter(os.Stdout, 2, 4, 1, ' ', 0)
 		defer tw.Flush()
 
-		fmt.Fprintf(tw, "ALIAS\tCOMMAND\n")
+		fmt.Fprintf(tw, "ALIAS\tPID\tCOMMAND\tANNOTATIONS\n")
 		for _, term := range resp.Terminals {
-			fmt.Fprintf(tw, "%s\t%s\n", term.Alias, strings.Join(term.Command, " "))
+			annotations := make([]string, 0, len(term.Annotations))
+			for k, v := range term.Annotations {
+				annotations = append(annotations, fmt.Sprintf("%s=%s", k, v))
+			}
+			sort.Slice(annotations, func(i, j int) bool { return annotations[i] < annotations[j] })
+			fmt.Fprintf(tw, "%s\t%d\t%s\t%s\n", term.Alias, term.Pid, strings.Join(term.Command, " "), strings.Join(annotations, ","))
 		}
 	},
 }
diff --git a/components/supervisor/pkg/ports/ports.go b/components/supervisor/pkg/ports/ports.go
index 7d975fc1e141fd..f4034c30c655fb 100644
--- a/components/supervisor/pkg/ports/ports.go
+++ b/components/supervisor/pkg/ports/ports.go
@@ -103,8 +103,11 @@ func (s *Subscription) Updates() <-chan []*api.PortsStatus {
 }
 
 // Run starts the port manager which keeps running until one of its observers stops.
-func (pm *Manager) Run() {
-	ctx, cancel := context.WithCancel(context.Background())
+func (pm *Manager) Run(ctx context.Context, wg *sync.WaitGroup) {
+	defer wg.Done()
+	defer log.Debug("portManager shutdown")
+
+	ctx, cancel := context.WithCancel(ctx)
 	defer func() {
 		// We copy the subscriptions to a list prior to closing them, to prevent a data race
 		// between the map iteration and entry removal when closing the subscription.
diff --git a/components/supervisor/pkg/ports/ports_test.go b/components/supervisor/pkg/ports/ports_test.go
index c097e23560eecd..7961dfea1bbbe7 100644
--- a/components/supervisor/pkg/ports/ports_test.go
+++ b/components/supervisor/pkg/ports/ports_test.go
@@ -471,12 +471,11 @@ func TestPortsUpdateState(t *testing.T) {
 				return ioutil.NopCloser(nil), nil
 			}
 
+			ctx, cancel := context.WithCancel(context.Background())
+			defer cancel()
 			var wg sync.WaitGroup
 			wg.Add(3)
-			go func() {
-				defer wg.Done()
-				pm.Run()
-			}()
+			go pm.Run(ctx, &wg)
 			sub, err := pm.Subscribe()
 			if err != nil {
 				t.Fatal(err)
@@ -607,12 +606,11 @@ func TestPortsConcurrentSubscribe(t *testing.T) {
 		return ioutil.NopCloser(nil), nil
 	}
 
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
 	var wg sync.WaitGroup
 	wg.Add(2)
-	go func() {
-		defer wg.Done()
-		pm.Run()
-	}()
+	go pm.Run(ctx, &wg)
 	go func() {
 		defer wg.Done()
 		defer close(config.Error)
diff --git a/components/supervisor/pkg/supervisor/supervisor.go b/components/supervisor/pkg/supervisor/supervisor.go
index bfee1f0330a8e4..b15d482c22a427 100644
--- a/components/supervisor/pkg/supervisor/supervisor.go
+++ b/components/supervisor/pkg/supervisor/supervisor.go
@@ -5,6 +5,7 @@
 package supervisor
 
 import (
+	"bufio"
 	"context"
 	"encoding/json"
 	"fmt"
@@ -14,6 +15,7 @@ import (
 	"os"
 	"os/exec"
 	"os/signal"
+	"path/filepath"
 	"runtime"
 	"strconv"
 	"strings"
@@ -169,20 +171,30 @@ func Run(options ...RunOption) {
 	}
 	apiServices = append(apiServices, additionalServices...)
 
+	// The reaper can be turned into a terminating reaper by writing true to this channel.
+	// When in terminating mode, the reaper will send SIGTERM to each child that gets reparented
+	// to us and is still running. We use this mechanism to send SIGTERM to a shell child processes
+	// that get reparented once their parent shell terminates during shutdown.
+	terminatingReaper := make(chan bool)
+	// We keep the reaper until the bitter end because:
+	//   - it doesn't need graceful shutdown
+	//   - we want to do as much work as possible (SIGTERM'ing reparented processes during shutdown).
+	go reaper(terminatingReaper)
+
+	var ideWG sync.WaitGroup
+	ideWG.Add(1)
+	go startAndWatchIDE(ctx, cfg, &ideWG, ideReady)
+
 	var wg sync.WaitGroup
-	wg.Add(6)
-	go reaper(ctx, &wg)
-	go startAndWatchIDE(ctx, cfg, &wg, ideReady)
+	wg.Add(4)
 	go startContentInit(ctx, cfg, &wg, cstate)
 	go startAPIEndpoint(ctx, cfg, &wg, apiServices, apiEndpointOpts...)
 	go taskManager.Run(ctx, &wg)
-	go func() {
-		defer wg.Done()
-		if cfg.isHeadless() {
-			return
-		}
-		portMgmt.Run()
-	}()
+
+	if !cfg.isHeadless() {
+		wg.Add(1)
+		go portMgmt.Run(ctx, &wg)
+	}
 
 	if cfg.PreventMetadataAccess {
 		go func() {
@@ -203,15 +215,21 @@ func Run(options ...RunOption) {
 	}
 
 	log.Info("received SIGTERM - tearing down")
+	terminatingReaper <- true
+	cancel()
 	err = termMux.Close()
 	if err != nil {
 		log.WithError(err).Error("terminal closure failed")
 	}
+
+	// terminate all child processes once the IDE is gone
+	ideWG.Wait()
+	terminateChildProcesses()
+
 	if !opts.InNamespace {
 		callDaemonTeardown()
 	}
 
-	cancel()
 	wg.Wait()
 }
 
@@ -305,16 +323,17 @@ func hasMetadataAccess() bool {
 	return false
 }
 
-func reaper(ctx context.Context, wg *sync.WaitGroup) {
-	defer wg.Done()
+func reaper(terminatingReaper <-chan bool) {
+	defer log.Debug("reaper shutdown")
 
+	var terminating bool
 	sigs := make(chan os.Signal, 128)
 	signal.Notify(sigs, syscall.SIGCHLD)
 	for {
 		select {
-		case <-ctx.Done():
-			return
 		case <-sigs:
+		case terminating = <-terminatingReaper:
+			continue
 		}
 
 		pid, err := unix.Wait4(-1, nil, 0, nil)
@@ -325,12 +344,33 @@ func reaper(ctx context.Context, wg *sync.WaitGroup) {
 		}
 		if err != nil {
 			log.WithField("pid", pid).WithError(err).Debug("cannot call waitpid() for re-parented child")
+			continue
+		}
+
+		if !terminating {
+			continue
+		}
+		proc, err := os.FindProcess(pid)
+		if err != nil {
+			log.WithField("pid", pid).WithError(err).Debug("cannot find re-parented process")
+			continue
 		}
+		err = proc.Signal(syscall.SIGTERM)
+		if err != nil {
+			if !strings.Contains(err.Error(), "os: process already finished") {
+				log.WithField("pid", pid).WithError(err).Debug("cannot send SIGTERM to re-parented process")
+			}
+
+			continue
+		}
+		log.WithField("pid", pid).Debug("SIGTERM'ed reparented child process")
 	}
 }
 
 func startAndWatchIDE(ctx context.Context, cfg *Config, wg *sync.WaitGroup, ideReady *ideReadyState) {
 	defer wg.Done()
+	defer log.Debug("startAndWatchIDE shutdown")
+
 	if cfg.isHeadless() {
 		ideReady.Set(true)
 		return
@@ -383,7 +423,7 @@ supervisorLoop:
 			}()
 
 			err = cmd.Wait()
-			if err != nil && !strings.Contains(err.Error(), "signal: interrupt") {
+			if err != nil && !(strings.Contains(err.Error(), "signal: interrupt") || strings.Contains(err.Error(), "wait: no child processes")) {
 				log.WithError(err).Warn("IDE was stopped")
 			}
 
@@ -411,7 +451,7 @@ supervisorLoop:
 	case <-ideStopped:
 		return
 	case <-time.After(timeBudgetIDEShutdown):
-		log.Error("IDE did not stop in time - sending SIGKILL")
+		log.WithField("timeBudgetIDEShutdown", timeBudgetIDEShutdown.String()).Error("IDE did not stop in time - sending SIGKILL")
 		cmd.Process.Signal(syscall.SIGKILL)
 	}
 }
@@ -530,6 +570,7 @@ func isBlacklistedEnvvar(name string) bool {
 
 func startAPIEndpoint(ctx context.Context, cfg *Config, wg *sync.WaitGroup, services []RegisterableService, opts ...grpc.ServerOption) {
 	defer wg.Done()
+	defer log.Debug("startAPIEndpoint shutdown")
 
 	l, err := net.Listen("tcp", fmt.Sprintf(":%d", cfg.APIEndpointPort))
 	if err != nil {
@@ -642,6 +683,52 @@ func startContentInit(ctx context.Context, cfg *Config, wg *sync.WaitGroup, cst
 	cst.MarkContentReady(src)
 }
 
+func terminateChildProcesses() {
+	ppid := strconv.Itoa(os.Getpid())
+	dirs, err := ioutil.ReadDir("/proc")
+	if err != nil {
+		log.WithError(err).Warn("cannot terminate child processes")
+		return
+	}
+	for _, d := range dirs {
+		pid, err := strconv.Atoi(d.Name())
+		if err != nil {
+			// not a PID
+			continue
+		}
+		proc, err := os.FindProcess(pid)
+		if err != nil {
+			continue
+		}
+
+		var isChild bool
+		f, err := os.Open(filepath.Join("/proc", d.Name(), "status"))
+		if err != nil {
+			continue
+		}
+		scan := bufio.NewScanner(f)
+		for scan.Scan() {
+			l := strings.TrimSpace(scan.Text())
+			if !strings.HasPrefix(l, "PPid:") {
+				continue
+			}
+
+			isChild = strings.HasSuffix(l, ppid)
+			break
+		}
+		if !isChild {
+			continue
+		}
+
+		err = proc.Signal(unix.SIGTERM)
+		if err != nil {
+			log.WithError(err).WithField("pid", pid).Warn("cannot terminate child processe")
+			continue
+		}
+		log.WithField("pid", pid).Debug("SIGTERM'ed child process")
+	}
+}
+
 func callDaemonTeardown() {
 	log.Info("asking ws-daemon to tear down this workspace")
 	ctx, cancel := context.WithTimeout(context.Background(), timeBudgetDaemonTeardown)
diff --git a/components/supervisor/pkg/supervisor/tasks.go b/components/supervisor/pkg/supervisor/tasks.go
index 283f527920f78b..7c4702b0ca15ab 100644
--- a/components/supervisor/pkg/supervisor/tasks.go
+++ b/components/supervisor/pkg/supervisor/tasks.go
@@ -200,6 +200,8 @@ func (tm *tasksManager) init(ctx context.Context) {
 
 func (tm *tasksManager) Run(ctx context.Context, wg *sync.WaitGroup) {
 	defer wg.Done()
+	defer log.Debug("tasksManager shutdown")
+
 	tm.init(ctx)
 
 	for _, t := range tm.tasks {
diff --git a/components/supervisor/pkg/terminal/service.go b/components/supervisor/pkg/terminal/service.go
index 98e1161c3fb7d2..3f248dfb450adb 100644
--- a/components/supervisor/pkg/terminal/service.go
+++ b/components/supervisor/pkg/terminal/service.go
@@ -6,9 +6,11 @@ package terminal
 
 import (
 	"context"
+	"fmt"
 	"io"
 	"os"
 	"os/exec"
+	"path/filepath"
 	"time"
 
 	"github.com/creack/pty"
@@ -65,17 +67,26 @@ func (srv *MuxTerminalService) RegisterREST(mux *runtime.ServeMux, grpcEndpoint
 func (srv *MuxTerminalService) Open(ctx context.Context, req *api.OpenTerminalRequest) (*api.OpenTerminalResponse, error) {
 	return srv.OpenWithOptions(ctx, req, TermOptions{
 		ReadTimeout: 5 * time.Second,
+		Annotations: req.Annotations,
 	})
 }
 
-// OpenWithOptions opens a new terminal running the shell with given options
+// OpenWithOptions opens a new terminal running the shell with given options.
+// req.Annotations override options.Annotations.
 func (srv *MuxTerminalService) OpenWithOptions(ctx context.Context, req *api.OpenTerminalRequest, options TermOptions) (*api.OpenTerminalResponse, error) {
 	cmd := exec.Command(srv.DefaultShell)
-	cmd.Dir = srv.DefaultWorkdir
+	if req.Workdir == "" {
+		cmd.Dir = srv.DefaultWorkdir
+	} else {
+		cmd.Dir = req.Workdir
+	}
 	cmd.Env = append(srv.Env, "TERM=xterm-color")
 	for key, value := range req.Env {
 		cmd.Env = append(cmd.Env, key+"="+value)
 	}
+	for k, v := range req.Annotations {
+		options.Annotations[k] = v
+	}
 	alias, err := srv.Mux.Start(cmd, options)
 	if err != nil {
 		return nil, status.Error(codes.Internal, err.Error())
@@ -110,9 +121,27 @@ func (srv *MuxTerminalService) List(ctx context.Context, req *api.ListTerminalsR
 
 	res := make([]*api.ListTerminalsResponse_Terminal, 0, len(srv.Mux.terms))
 	for alias, term := range srv.Mux.terms {
+		var (
+			pid int64
+			cwd string
+			err error
+		)
+		if proc := term.Command.Process; proc != nil {
+			pid = int64(proc.Pid)
+			cwd, err = filepath.EvalSymlinks(fmt.Sprintf("/proc/%d/cwd", pid))
+			if err != nil {
+				log.WithError(err).WithField("pid", pid).Warn("unable to resolve terminal's current working dir")
+				cwd = term.Command.Dir
+			}
+		}
+
 		res = append(res, &api.ListTerminalsResponse_Terminal{
-			Alias:   alias,
-			Command: term.Command.Args,
+			Alias:          alias,
+			Command:        term.Command.Args,
+			Pid:            pid,
+			InitialWorkdir: term.Command.Dir,
+			CurrentWorkdir: cwd,
+			Annotations:    term.Annotations,
 		})
 	}
 
diff --git a/components/supervisor/pkg/terminal/terminal.go b/components/supervisor/pkg/terminal/terminal.go
index 0714d894e9a597..b039e91b4f5a6e 100644
--- a/components/supervisor/pkg/terminal/terminal.go
+++ b/components/supervisor/pkg/terminal/terminal.go
@@ -85,8 +85,8 @@ func (m *Mux) Close() error {
 	var err error
 	for k := range m.terms {
 		cerr := m.doClose(k, closeTerminaldefaultGracePeriod)
-		if cerr == nil {
-			log.WithError(err).WithField("alias", k).Warn("cannot properly close terminal")
+		if cerr != nil {
+			log.WithError(cerr).WithField("alias", k).Warn("cannot properly close terminal")
 			if err != nil {
 				err = cerr
 			}
@@ -142,7 +142,7 @@ func gracefullyShutdownProcess(p *os.Process, gracePeriod time.Duration) error {
 		return p.Kill()
 	}
 
-	err := p.Signal(unix.SIGINT)
+	err := p.Signal(unix.SIGTERM)
 	if err != nil {
 		return err
 	}
@@ -192,6 +192,7 @@ func newTerm(pty *os.File, cmd *exec.Cmd, options TermOptions) (*Term, error) {
 			listener: make(map[*multiWriterListener]struct{}),
 			recorder: recorder,
 		},
+		Annotations: options.Annotations,
 
 		StarterToken: token.String(),
 
@@ -205,6 +206,9 @@ func newTerm(pty *os.File, cmd *exec.Cmd, options TermOptions) (*Term, error) {
 type TermOptions struct {
 	// timeout after which a listener is dropped. Use 0 for no timeout.
 	ReadTimeout time.Duration
+
+	// Annotations are user-defined metadata that's attached to a terminal
+	Annotations map[string]string
 }
 
 // Term is a pseudo-terminal
@@ -213,6 +217,7 @@ type Term struct {
 	Command      *exec.Cmd
 	Title        string
 	StarterToken string
+	Annotations  map[string]string
 
 	Stdout *multiWriter
 
diff --git a/components/supervisor/pkg/terminal/terminal_test.go b/components/supervisor/pkg/terminal/terminal_test.go
index bf736755e7447c..166202378f15ae 100644
--- a/components/supervisor/pkg/terminal/terminal_test.go
+++ b/components/supervisor/pkg/terminal/terminal_test.go
@@ -18,6 +18,86 @@ import (
 	"golang.org/x/sync/errgroup"
 )
 
+func TestAnnotations(t *testing.T) {
+	tests := []struct {
+		Desc        string
+		Req         *api.OpenTerminalRequest
+		Opts        *TermOptions
+		Expectation map[string]string
+	}{
+		{
+			Desc: "no annotations",
+			Req: &api.OpenTerminalRequest{
+				Annotations: map[string]string{},
+			},
+			Expectation: map[string]string{},
+		},
+		{
+			Desc: "request annotation",
+			Req: &api.OpenTerminalRequest{
+				Annotations: map[string]string{
+					"hello": "world",
+				},
+			},
+			Expectation: map[string]string{
+				"hello": "world",
+			},
+		},
+		{
+			Desc: "option annotation",
+			Req: &api.OpenTerminalRequest{
+				Annotations: map[string]string{
+					"hello": "world",
+				},
+			},
+			Opts: &TermOptions{
+				Annotations: map[string]string{
+					"hello": "foo",
+					"bar":   "baz",
+				},
+			},
+			Expectation: map[string]string{
+				"hello": "world",
+				"bar":   "baz",
+			},
+		},
+	}
+
+	for _, test := range tests {
+		t.Run(test.Desc, func(t *testing.T) {
+			mux := NewMux()
+			defer mux.Close()
+
+			terminalService := NewMuxTerminalService(mux)
+			var err error
+			if test.Opts == nil {
+				_, err = terminalService.Open(context.Background(), test.Req)
+			} else {
+				_, err = terminalService.OpenWithOptions(context.Background(), test.Req, *test.Opts)
+			}
+			if err != nil {
+				t.Fatal(err)
+				return
+			}
+
+			lr, err := terminalService.List(context.Background(), &api.ListTerminalsRequest{})
+			if err != nil {
+				t.Fatal(err)
+				return
+			}
+			if len(lr.Terminals) != 1 {
+				t.Fatalf("expected exactly one terminal, got %d", len(lr.Terminals))
+				return
+			}
+
+			if diff := cmp.Diff(test.Expectation, lr.Terminals[0].Annotations); diff != "" {
+				t.Errorf("unexpected output (-want +got):\n%s", diff)
+			}
+		})
+
+	}
+}
+
 func TestTerminals(t *testing.T) {
 	tests := []struct {
 		Desc        string
diff --git a/dev/addlicense/BUILD.yaml b/dev/addlicense/BUILD.yaml
index 8afcf20d00e66d..d058205e54025e 100644
--- a/dev/addlicense/BUILD.yaml
+++ b/dev/addlicense/BUILD.yaml
@@ -9,3 +9,6 @@ packages:
     env:
       - CGO_ENABLED=0
       - GOOS=linux
+    config:
+      dontLint: true
+      dontTest: true
\ No newline at end of file
diff --git a/test/leeway-build.sh b/test/leeway-build.sh
index 8dc467793dba6d..29bb7333a32824 100755
--- a/test/leeway-build.sh
+++ b/test/leeway-build.sh
@@ -1,4 +1,8 @@
 #!/bin/bash
+# Copyright (c) 2021 Gitpod GmbH. All rights reserved.
+# Licensed under the GNU Affero General Public License (AGPL).
+# See License-AGPL.txt in the project root for license information.
+
 
 mkdir -p bin