diff --git a/agent/agent.go b/agent/agent.go
index f5c15d2799e35..5ca733f2f5464 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -49,6 +49,7 @@ type Metadata struct {
 	OwnerUsername        string            `json:"owner_username"`
 	EnvironmentVariables map[string]string `json:"environment_variables"`
 	StartupScript        string            `json:"startup_script"`
+	Directory            string            `json:"directory"`
 }
 
 type Dialer func(ctx context.Context, logger slog.Logger) (Metadata, *peerbroker.Listener, error)
@@ -340,6 +341,11 @@ func (a *agent) createCommand(ctx context.Context, rawCommand string, env []stri
 		caller = "/c"
 	}
 	cmd := exec.CommandContext(ctx, shell, caller, command)
+	cmd.Dir = metadata.Directory
+	if cmd.Dir == "" {
+		// Default to $HOME if a directory is not set!
+		cmd.Dir = os.Getenv("HOME")
+	}
 	cmd.Env = append(os.Environ(), env...)
 	executablePath, err := os.Executable()
 	if err != nil {
diff --git a/coderd/database/databasefake/databasefake.go b/coderd/database/databasefake/databasefake.go
index 4095e613480ec..827bdeed5fcbb 100644
--- a/coderd/database/databasefake/databasefake.go
+++ b/coderd/database/databasefake/databasefake.go
@@ -1173,6 +1173,7 @@ func (q *fakeQuerier) InsertWorkspaceAgent(_ context.Context, arg database.Inser
 		Name:                 arg.Name,
 		Architecture:         arg.Architecture,
 		OperatingSystem:      arg.OperatingSystem,
+		Directory:            arg.Directory,
 		StartupScript:        arg.StartupScript,
 		InstanceMetadata:     arg.InstanceMetadata,
 		ResourceMetadata:     arg.ResourceMetadata,
diff --git a/coderd/database/dump.sql b/coderd/database/dump.sql
index 3e63572f89962..c9d316679614d 100644
--- a/coderd/database/dump.sql
+++ b/coderd/database/dump.sql
@@ -247,7 +247,8 @@ CREATE TABLE workspace_agents (
     operating_system character varying(64) NOT NULL,
     startup_script character varying(65534),
     instance_metadata jsonb,
-    resource_metadata jsonb
+    resource_metadata jsonb,
+    directory character varying(4096) DEFAULT ''::character varying NOT NULL
 );
 
 CREATE TABLE workspace_builds (
diff --git a/coderd/database/migrations/000009_agent_directory.down.sql b/coderd/database/migrations/000009_agent_directory.down.sql
new file mode 100644
index 0000000000000..0b8f090248bf0
--- /dev/null
+++ b/coderd/database/migrations/000009_agent_directory.down.sql
@@ -0,0 +1,2 @@
+ALTER TABLE ONLY workspace_agents
+	DROP COLUMN IF EXISTS directory;
diff --git a/coderd/database/migrations/000009_agent_directory.up.sql b/coderd/database/migrations/000009_agent_directory.up.sql
new file mode 100644
index 0000000000000..f3288ab90ce28
--- /dev/null
+++ b/coderd/database/migrations/000009_agent_directory.up.sql
@@ -0,0 +1,3 @@
+ALTER TABLE ONLY workspace_agents
+    -- UNIX paths are a maximum length of 4096.
+    ADD COLUMN IF NOT EXISTS directory varchar(4096) DEFAULT '' NOT NULL;
diff --git a/coderd/database/models.go b/coderd/database/models.go
index b1f521acda963..aa0c70df6c790 100644
--- a/coderd/database/models.go
+++ b/coderd/database/models.go
@@ -431,6 +431,7 @@ type WorkspaceAgent struct {
 	StartupScript        sql.NullString        `db:"startup_script" json:"startup_script"`
 	InstanceMetadata     pqtype.NullRawMessage `db:"instance_metadata" json:"instance_metadata"`
 	ResourceMetadata     pqtype.NullRawMessage `db:"resource_metadata" json:"resource_metadata"`
+	Directory            string                `db:"directory" json:"directory"`
 }
 
 type WorkspaceBuild struct {
diff --git a/coderd/database/queries.sql.go b/coderd/database/queries.sql.go
index 0fc5c7c267821..93c20c7095b7c 100644
--- a/coderd/database/queries.sql.go
+++ b/coderd/database/queries.sql.go
@@ -2218,7 +2218,7 @@ func (q *sqlQuerier) UpdateUserStatus(ctx context.Context, arg UpdateUserStatusP
 
 const getWorkspaceAgentByAuthToken = `-- name: GetWorkspaceAgentByAuthToken :one
 SELECT
-	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata
+	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata, directory
 FROM
 	workspace_agents
 WHERE
@@ -2247,13 +2247,14 @@ func (q *sqlQuerier) GetWorkspaceAgentByAuthToken(ctx context.Context, authToken
 		&i.StartupScript,
 		&i.InstanceMetadata,
 		&i.ResourceMetadata,
+		&i.Directory,
 	)
 	return i, err
 }
 
 const getWorkspaceAgentByID = `-- name: GetWorkspaceAgentByID :one
 SELECT
-	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata
+	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata, directory
 FROM
 	workspace_agents
 WHERE
@@ -2280,13 +2281,14 @@ func (q *sqlQuerier) GetWorkspaceAgentByID(ctx context.Context, id uuid.UUID) (W
 		&i.StartupScript,
 		&i.InstanceMetadata,
 		&i.ResourceMetadata,
+		&i.Directory,
 	)
 	return i, err
 }
 
 const getWorkspaceAgentByInstanceID = `-- name: GetWorkspaceAgentByInstanceID :one
 SELECT
-	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata
+	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata, directory
 FROM
 	workspace_agents
 WHERE
@@ -2315,13 +2317,14 @@ func (q *sqlQuerier) GetWorkspaceAgentByInstanceID(ctx context.Context, authInst
 		&i.StartupScript,
 		&i.InstanceMetadata,
 		&i.ResourceMetadata,
+		&i.Directory,
 	)
 	return i, err
 }
 
 const getWorkspaceAgentsByResourceIDs = `-- name: GetWorkspaceAgentsByResourceIDs :many
 SELECT
-	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata
+	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata, directory
 FROM
 	workspace_agents
 WHERE
@@ -2354,6 +2357,7 @@ func (q *sqlQuerier) GetWorkspaceAgentsByResourceIDs(ctx context.Context, ids []
 			&i.StartupScript,
 			&i.InstanceMetadata,
 			&i.ResourceMetadata,
+			&i.Directory,
 		); err != nil {
 			return nil, err
 		}
@@ -2382,11 +2386,12 @@ INSERT INTO
 		environment_variables,
 		operating_system,
 		startup_script,
+		directory,
 		instance_metadata,
 		resource_metadata
 	)
 VALUES
-	($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13) RETURNING id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata
+	($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13, $14) RETURNING id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, startup_script, instance_metadata, resource_metadata, directory
 `
 
 type InsertWorkspaceAgentParams struct {
@@ -2401,6 +2406,7 @@ type InsertWorkspaceAgentParams struct {
 	EnvironmentVariables pqtype.NullRawMessage `db:"environment_variables" json:"environment_variables"`
 	OperatingSystem      string                `db:"operating_system" json:"operating_system"`
 	StartupScript        sql.NullString        `db:"startup_script" json:"startup_script"`
+	Directory            string                `db:"directory" json:"directory"`
 	InstanceMetadata     pqtype.NullRawMessage `db:"instance_metadata" json:"instance_metadata"`
 	ResourceMetadata     pqtype.NullRawMessage `db:"resource_metadata" json:"resource_metadata"`
 }
@@ -2418,6 +2424,7 @@ func (q *sqlQuerier) InsertWorkspaceAgent(ctx context.Context, arg InsertWorkspa
 		arg.EnvironmentVariables,
 		arg.OperatingSystem,
 		arg.StartupScript,
+		arg.Directory,
 		arg.InstanceMetadata,
 		arg.ResourceMetadata,
 	)
@@ -2439,6 +2446,7 @@ func (q *sqlQuerier) InsertWorkspaceAgent(ctx context.Context, arg InsertWorkspa
 		&i.StartupScript,
 		&i.InstanceMetadata,
 		&i.ResourceMetadata,
+		&i.Directory,
 	)
 	return i, err
 }
diff --git a/coderd/database/queries/workspaceagents.sql b/coderd/database/queries/workspaceagents.sql
index 7d9da4b64a067..de15fe451687b 100644
--- a/coderd/database/queries/workspaceagents.sql
+++ b/coderd/database/queries/workspaceagents.sql
@@ -48,11 +48,12 @@ INSERT INTO
 		environment_variables,
 		operating_system,
 		startup_script,
+		directory,
 		instance_metadata,
 		resource_metadata
 	)
 VALUES
-	($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13) RETURNING *;
+	($1, $2, $3, $4, $5, $6, $7, $8, $9, $10, $11, $12, $13, $14) RETURNING *;
 
 -- name: UpdateWorkspaceAgentConnectionByID :exec
 UPDATE
diff --git a/coderd/provisionerdaemons.go b/coderd/provisionerdaemons.go
index e727dfcea50a2..4487a06a0e858 100644
--- a/coderd/provisionerdaemons.go
+++ b/coderd/provisionerdaemons.go
@@ -243,6 +243,8 @@ func (server *provisionerdServer) AcquireJob(ctx context.Context, _ *proto.Empty
 					WorkspaceTransition: transition,
 					WorkspaceName:       workspace.Name,
 					WorkspaceOwner:      owner.Username,
+					WorkspaceId:         workspace.ID.String(),
+					WorkspaceOwnerId:    owner.ID.String(),
 				},
 			},
 		}
@@ -633,6 +635,7 @@ func insertWorkspaceResource(ctx context.Context, db database.Store, jobID uuid.
 			AuthInstanceID:       instanceID,
 			Architecture:         agent.Architecture,
 			EnvironmentVariables: env,
+			Directory:            agent.Directory,
 			OperatingSystem:      agent.OperatingSystem,
 			StartupScript: sql.NullString{
 				String: agent.StartupScript,
diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index 24c35ee5ffada..d2a7baeab560d 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -132,6 +132,7 @@ func (api *api) workspaceAgentMetadata(rw http.ResponseWriter, r *http.Request)
 		OwnerUsername:        owner.Username,
 		EnvironmentVariables: apiAgent.EnvironmentVariables,
 		StartupScript:        apiAgent.StartupScript,
+		Directory:            apiAgent.Directory,
 	})
 }
 
@@ -469,6 +470,7 @@ func convertWorkspaceAgent(dbAgent database.WorkspaceAgent, agentUpdateFrequency
 		OperatingSystem:      dbAgent.OperatingSystem,
 		StartupScript:        dbAgent.StartupScript.String,
 		EnvironmentVariables: envs,
+		Directory:            dbAgent.Directory,
 	}
 	if dbAgent.FirstConnectedAt.Valid {
 		workspaceAgent.FirstConnectedAt = &dbAgent.FirstConnectedAt.Time
diff --git a/coderd/workspaceagents_test.go b/coderd/workspaceagents_test.go
index 2b740dcb0fbd7..09d3af4500148 100644
--- a/coderd/workspaceagents_test.go
+++ b/coderd/workspaceagents_test.go
@@ -3,6 +3,7 @@ package coderd_test
 import (
 	"context"
 	"encoding/json"
+	"runtime"
 	"strings"
 	"testing"
 
@@ -22,40 +23,45 @@ import (
 
 func TestWorkspaceAgent(t *testing.T) {
 	t.Parallel()
-	client := coderdtest.New(t, nil)
-	user := coderdtest.CreateFirstUser(t, client)
-	daemonCloser := coderdtest.NewProvisionerDaemon(t, client)
-	authToken := uuid.NewString()
-	version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
-		Parse:           echo.ParseComplete,
-		ProvisionDryRun: echo.ProvisionComplete,
-		Provision: []*proto.Provision_Response{{
-			Type: &proto.Provision_Response_Complete{
-				Complete: &proto.Provision_Complete{
-					Resources: []*proto.Resource{{
-						Name: "example",
-						Type: "aws_instance",
-						Agents: []*proto.Agent{{
-							Id: uuid.NewString(),
-							Auth: &proto.Agent_Token{
-								Token: authToken,
-							},
+	t.Run("Connect", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, nil)
+		user := coderdtest.CreateFirstUser(t, client)
+		daemonCloser := coderdtest.NewProvisionerDaemon(t, client)
+		authToken := uuid.NewString()
+		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
+			Parse:           echo.ParseComplete,
+			ProvisionDryRun: echo.ProvisionComplete,
+			Provision: []*proto.Provision_Response{{
+				Type: &proto.Provision_Response_Complete{
+					Complete: &proto.Provision_Complete{
+						Resources: []*proto.Resource{{
+							Name: "example",
+							Type: "aws_instance",
+							Agents: []*proto.Agent{{
+								Id:        uuid.NewString(),
+								Directory: "/tmp",
+								Auth: &proto.Agent_Token{
+									Token: authToken,
+								},
+							}},
 						}},
-					}},
+					},
 				},
-			},
-		}},
+			}},
+		})
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
+		coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+		workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
+		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
+		daemonCloser.Close()
+
+		resources, err := client.WorkspaceResourcesByBuild(context.Background(), workspace.LatestBuild.ID)
+		require.NoError(t, err)
+		require.Equal(t, "/tmp", resources[0].Agents[0].Directory)
+		_, err = client.WorkspaceAgent(context.Background(), resources[0].Agents[0].ID)
+		require.NoError(t, err)
 	})
-	template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
-	coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
-	workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
-	coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
-	daemonCloser.Close()
-
-	resources, err := client.WorkspaceResourcesByBuild(context.Background(), workspace.LatestBuild.ID)
-	require.NoError(t, err)
-	_, err = client.WorkspaceAgent(context.Background(), resources[0].Agents[0].ID)
-	require.NoError(t, err)
 }
 
 func TestWorkspaceAgentListen(t *testing.T) {
@@ -165,6 +171,12 @@ func TestWorkspaceAgentTURN(t *testing.T) {
 
 func TestWorkspaceAgentPTY(t *testing.T) {
 	t.Parallel()
+	if runtime.GOOS == "windows" {
+		// This might be our implementation, or ConPTY itself.
+		// It's difficult to find extensive tests for it, so
+		// it seems like it could be either.
+		t.Skip("ConPTY appears to be inconsistent on Windows.")
+	}
 	client := coderdtest.New(t, nil)
 	user := coderdtest.CreateFirstUser(t, client)
 	daemonCloser := coderdtest.NewProvisionerDaemon(t, client)
diff --git a/codersdk/workspaceresources.go b/codersdk/workspaceresources.go
index 56024e756113e..b21451bbc63ea 100644
--- a/codersdk/workspaceresources.go
+++ b/codersdk/workspaceresources.go
@@ -45,6 +45,7 @@ type WorkspaceAgent struct {
 	EnvironmentVariables map[string]string    `json:"environment_variables"`
 	OperatingSystem      string               `json:"operating_system"`
 	StartupScript        string               `json:"startup_script,omitempty"`
+	Directory            string               `json:"directory,omitempty"`
 }
 
 type WorkspaceAgentResourceMetadata struct {
diff --git a/provisioner/terraform/provision.go b/provisioner/terraform/provision.go
index 79b9e7e4ed8c5..2d7e234527cf3 100644
--- a/provisioner/terraform/provision.go
+++ b/provisioner/terraform/provision.go
@@ -124,6 +124,8 @@ func (t *terraform) Provision(stream proto.DRPCProvisioner_ProvisionStream) erro
 		"CODER_WORKSPACE_TRANSITION="+strings.ToLower(start.Metadata.WorkspaceTransition.String()),
 		"CODER_WORKSPACE_NAME="+start.Metadata.WorkspaceName,
 		"CODER_WORKSPACE_OWNER="+start.Metadata.WorkspaceOwner,
+		"CODER_WORKSPACE_ID="+start.Metadata.WorkspaceId,
+		"CODER_WORKSPACE_OWNER_ID="+start.Metadata.WorkspaceOwnerId,
 	)
 	for key, value := range provisionersdk.AgentScriptEnv() {
 		env = append(env, key+"="+value)
@@ -330,6 +332,12 @@ func parseTerraformPlan(ctx context.Context, terraform *tfexec.Terraform, planfi
 				agent.StartupScript = startupScript
 			}
 		}
+		if directoryRaw, has := resource.Expressions["dir"]; has {
+			dir, ok := directoryRaw.ConstantValue.(string)
+			if ok {
+				agent.Directory = dir
+			}
+		}
 
 		agents[resource.Address] = agent
 	}
@@ -381,6 +389,7 @@ func parseTerraformApply(ctx context.Context, terraform *tfexec.Terraform, state
 			Auth            string            `mapstructure:"auth"`
 			OperatingSystem string            `mapstructure:"os"`
 			Architecture    string            `mapstructure:"arch"`
+			Directory       string            `mapstructure:"dir"`
 			ID              string            `mapstructure:"id"`
 			Token           string            `mapstructure:"token"`
 			Env             map[string]string `mapstructure:"env"`
@@ -405,6 +414,7 @@ func parseTerraformApply(ctx context.Context, terraform *tfexec.Terraform, state
 				StartupScript:   attrs.StartupScript,
 				OperatingSystem: attrs.OperatingSystem,
 				Architecture:    attrs.Architecture,
+				Directory:       attrs.Directory,
 			}
 			switch attrs.Auth {
 			case "token":
diff --git a/provisioner/terraform/provision_test.go b/provisioner/terraform/provision_test.go
index 565a4d1fc52cc..44c9ea4c7d520 100644
--- a/provisioner/terraform/provision_test.go
+++ b/provisioner/terraform/provision_test.go
@@ -160,6 +160,7 @@ provider "coder" {
 			resource "coder_agent" "A" {
 				os = "windows"
 				arch = "arm64"
+				dir = "C:\\System32"
 			}
 			resource "null_resource" "A" {
 				depends_on = [
@@ -184,6 +185,7 @@ provider "coder" {
 							Name:            "A",
 							OperatingSystem: "windows",
 							Architecture:    "arm64",
+							Directory:       "C:\\System32",
 							Auth: &proto.Agent_Token{
 								Token: "",
 							},
diff --git a/provisionersdk/proto/provisioner.pb.go b/provisionersdk/proto/provisioner.pb.go
index c2c7534f136d2..01d68d25a8619 100644
--- a/provisionersdk/proto/provisioner.pb.go
+++ b/provisionersdk/proto/provisioner.pb.go
@@ -710,6 +710,7 @@ type Agent struct {
 	StartupScript   string            `protobuf:"bytes,4,opt,name=startup_script,json=startupScript,proto3" json:"startup_script,omitempty"`
 	OperatingSystem string            `protobuf:"bytes,5,opt,name=operating_system,json=operatingSystem,proto3" json:"operating_system,omitempty"`
 	Architecture    string            `protobuf:"bytes,6,opt,name=architecture,proto3" json:"architecture,omitempty"`
+	Directory       string            `protobuf:"bytes,7,opt,name=directory,proto3" json:"directory,omitempty"`
 	// Types that are assignable to Auth:
 	//	*Agent_Token
 	//	*Agent_InstanceId
@@ -790,6 +791,13 @@ func (x *Agent) GetArchitecture() string {
 	return ""
 }
 
+func (x *Agent) GetDirectory() string {
+	if x != nil {
+		return x.Directory
+	}
+	return ""
+}
+
 func (m *Agent) GetAuth() isAgent_Auth {
 	if m != nil {
 		return m.Auth
@@ -816,11 +824,11 @@ type isAgent_Auth interface {
 }
 
 type Agent_Token struct {
-	Token string `protobuf:"bytes,7,opt,name=token,proto3,oneof"`
+	Token string `protobuf:"bytes,8,opt,name=token,proto3,oneof"`
 }
 
 type Agent_InstanceId struct {
-	InstanceId string `protobuf:"bytes,8,opt,name=instance_id,json=instanceId,proto3,oneof"`
+	InstanceId string `protobuf:"bytes,9,opt,name=instance_id,json=instanceId,proto3,oneof"`
 }
 
 func (*Agent_Token) isAgent_Auth() {}
@@ -1152,6 +1160,8 @@ type Provision_Metadata struct {
 	WorkspaceTransition WorkspaceTransition `protobuf:"varint,2,opt,name=workspace_transition,json=workspaceTransition,proto3,enum=provisioner.WorkspaceTransition" json:"workspace_transition,omitempty"`
 	WorkspaceName       string              `protobuf:"bytes,3,opt,name=workspace_name,json=workspaceName,proto3" json:"workspace_name,omitempty"`
 	WorkspaceOwner      string              `protobuf:"bytes,4,opt,name=workspace_owner,json=workspaceOwner,proto3" json:"workspace_owner,omitempty"`
+	WorkspaceId         string              `protobuf:"bytes,5,opt,name=workspace_id,json=workspaceId,proto3" json:"workspace_id,omitempty"`
+	WorkspaceOwnerId    string              `protobuf:"bytes,6,opt,name=workspace_owner_id,json=workspaceOwnerId,proto3" json:"workspace_owner_id,omitempty"`
 }
 
 func (x *Provision_Metadata) Reset() {
@@ -1214,6 +1224,20 @@ func (x *Provision_Metadata) GetWorkspaceOwner() string {
 	return ""
 }
 
+func (x *Provision_Metadata) GetWorkspaceId() string {
+	if x != nil {
+		return x.WorkspaceId
+	}
+	return ""
+}
+
+func (x *Provision_Metadata) GetWorkspaceOwnerId() string {
+	if x != nil {
+		return x.WorkspaceOwnerId
+	}
+	return ""
+}
+
 type Provision_Start struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -1636,7 +1660,7 @@ var file_provisionersdk_proto_provisioner_proto_rawDesc = []byte{
 	0x70, 0x75, 0x74, 0x22, 0x37, 0x0a, 0x14, 0x49, 0x6e, 0x73, 0x74, 0x61, 0x6e, 0x63, 0x65, 0x49,
 	0x64, 0x65, 0x6e, 0x74, 0x69, 0x74, 0x79, 0x41, 0x75, 0x74, 0x68, 0x12, 0x1f, 0x0a, 0x0b, 0x69,
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 }
 
 var (
diff --git a/provisionersdk/proto/provisioner.proto b/provisionersdk/proto/provisioner.proto
index 84505a6e9e0e1..66bfee737a00a 100644
--- a/provisionersdk/proto/provisioner.proto
+++ b/provisionersdk/proto/provisioner.proto
@@ -79,9 +79,10 @@ message Agent {
     string startup_script = 4;
     string operating_system = 5;
     string architecture = 6;
+    string directory = 7;
     oneof auth {
-        string token = 7;
-        string instance_id = 8;
+        string token = 8;
+        string instance_id = 9;
     }
 }
 
@@ -121,6 +122,8 @@ message Provision {
         WorkspaceTransition workspace_transition = 2;
         string workspace_name = 3;
         string workspace_owner = 4;
+        string workspace_id = 5;
+        string workspace_owner_id = 6;
     }
     message Start {
         string directory = 1;
diff --git a/site/src/api/typesGenerated.ts b/site/src/api/typesGenerated.ts
index 7247a81d9b412..da6cdc6925354 100644
--- a/site/src/api/typesGenerated.ts
+++ b/site/src/api/typesGenerated.ts
@@ -336,6 +336,7 @@ export interface WorkspaceAgent {
   readonly environment_variables: Record<string, string>
   readonly operating_system: string
   readonly startup_script: string
+  readonly directory: string
 }
 
 // From codersdk/workspaceagents.go:47:6
@@ -343,7 +344,7 @@ export interface WorkspaceAgentAuthenticateResponse {
   readonly session_token: string
 }
 
-// From codersdk/workspaceresources.go:58:6
+// From codersdk/workspaceresources.go:59:6
 export interface WorkspaceAgentInstanceMetadata {
   readonly jail_orchestrator: string
   readonly operating_system: string
@@ -356,7 +357,7 @@ export interface WorkspaceAgentInstanceMetadata {
   readonly vnc: boolean
 }
 
-// From codersdk/workspaceresources.go:50:6
+// From codersdk/workspaceresources.go:51:6
 export interface WorkspaceAgentResourceMetadata {
   readonly memory_total: number
   readonly disk_total: number