diff --git a/cmd/ctr/commands/containers/containers.go b/cmd/ctr/commands/containers/containers.go
index 9cf5df465..5bd9fb456 100644
--- a/cmd/ctr/commands/containers/containers.go
+++ b/cmd/ctr/commands/containers/containers.go
@@ -20,10 +20,10 @@ var Command = cli.Command{
 	Usage:   "manage containers",
 	Aliases: []string{"c"},
 	Subcommands: []cli.Command{
-		listCommand,
 		deleteCommand,
-		setLabelsCommand,
 		infoCommand,
+		listCommand,
+		setLabelsCommand,
 	},
 }
 
diff --git a/cmd/ctr/commands/content/content.go b/cmd/ctr/commands/content/content.go
index 2cfbeaa06..d3cd8da4e 100644
--- a/cmd/ctr/commands/content/content.go
+++ b/cmd/ctr/commands/content/content.go
@@ -27,16 +27,16 @@ var (
 		Name:  "content",
 		Usage: "manage content",
 		Subcommands: cli.Commands{
-			listCommand,
-			ingestCommand,
 			activeIngestCommand,
-			getCommand,
-			editCommand,
 			deleteCommand,
-			setLabelsCommand,
+			editCommand,
 			fetchCommand,
 			fetchObjectCommand,
+			getCommand,
+			ingestCommand,
+			listCommand,
 			pushObjectCommand,
+			setLabelsCommand,
 		},
 	}
 
diff --git a/cmd/ctr/commands/namespaces/namespaces.go b/cmd/ctr/commands/namespaces/namespaces.go
index ec0ba3739..bedaf8522 100644
--- a/cmd/ctr/commands/namespaces/namespaces.go
+++ b/cmd/ctr/commands/namespaces/namespaces.go
@@ -20,9 +20,9 @@ var Command = cli.Command{
 	Usage: "manage namespaces",
 	Subcommands: cli.Commands{
 		createCommand,
-		setLabelsCommand,
 		listCommand,
 		removeCommand,
+		setLabelsCommand,
 	},
 }
 
diff --git a/cmd/ctr/pprof.go b/cmd/ctr/commands/pprof/pprof.go
similarity index 95%
rename from cmd/ctr/pprof.go
rename to cmd/ctr/commands/pprof/pprof.go
index 68e232480..8192d1135 100644
--- a/cmd/ctr/pprof.go
+++ b/cmd/ctr/commands/pprof/pprof.go
@@ -1,4 +1,4 @@
-package main
+package pprof
 
 import (
 	"fmt"
@@ -17,7 +17,8 @@ type pprofDialer struct {
 	addr  string
 }
 
-var pprofCommand = cli.Command{
+// Command is the cli command for providing golang pprof outputs for containerd
+var Command = cli.Command{
 	Name:  "pprof",
 	Usage: "provide golang pprof outputs for containerd",
 	Flags: []cli.Flag{
@@ -28,12 +29,12 @@ var pprofCommand = cli.Command{
 		},
 	},
 	Subcommands: []cli.Command{
+		pprofBlockCommand,
 		pprofGoroutinesCommand,
 		pprofHeapCommand,
 		pprofProfileCommand,
-		pprofTraceCommand,
-		pprofBlockCommand,
 		pprofThreadcreateCommand,
+		pprofTraceCommand,
 	},
 }
 
@@ -91,7 +92,7 @@ var pprofTraceCommand = cli.Command{
 	Flags: []cli.Flag{
 		cli.DurationFlag{
 			Name:  "seconds,s",
-			Usage: "Trace time (seconds)",
+			Usage: "trace time (seconds)",
 			Value: time.Duration(5 * time.Second),
 		},
 	},
diff --git a/cmd/ctr/pprof_unix.go b/cmd/ctr/commands/pprof/pprof_unix.go
similarity index 94%
rename from cmd/ctr/pprof_unix.go
rename to cmd/ctr/commands/pprof/pprof_unix.go
index 009b5da5e..5d22e3edd 100644
--- a/cmd/ctr/pprof_unix.go
+++ b/cmd/ctr/commands/pprof/pprof_unix.go
@@ -1,6 +1,6 @@
 // +build !windows
 
-package main
+package pprof
 
 import "net"
 
diff --git a/cmd/ctr/pprof_windows.go b/cmd/ctr/commands/pprof/pprof_windows.go
similarity index 95%
rename from cmd/ctr/pprof_windows.go
rename to cmd/ctr/commands/pprof/pprof_windows.go
index c7bacebee..c59c175fe 100644
--- a/cmd/ctr/pprof_windows.go
+++ b/cmd/ctr/commands/pprof/pprof_windows.go
@@ -1,4 +1,4 @@
-package main
+package pprof
 
 import (
 	"net"
diff --git a/cmd/ctr/run.go b/cmd/ctr/commands/run/run.go
similarity index 64%
rename from cmd/ctr/run.go
rename to cmd/ctr/commands/run/run.go
index 88bacf2d2..184f6540a 100644
--- a/cmd/ctr/run.go
+++ b/cmd/ctr/commands/run/run.go
@@ -1,13 +1,16 @@
-package main
+package run
 
 import (
 	gocontext "context"
+	"encoding/csv"
 	"fmt"
 	"runtime"
+	"strings"
 
 	"github.com/containerd/console"
 	"github.com/containerd/containerd"
 	"github.com/containerd/containerd/cmd/ctr/commands"
+	"github.com/containerd/containerd/cmd/ctr/commands/tasks"
 	"github.com/containerd/containerd/containers"
 	specs "github.com/opencontainers/runtime-spec/specs-go"
 	"github.com/pkg/errors"
@@ -15,10 +18,6 @@ import (
 	"github.com/urfave/cli"
 )
 
-type resizer interface {
-	Resize(ctx gocontext.Context, w, h uint32) error
-}
-
 func withEnv(context *cli.Context) containerd.SpecOpts {
 	return func(_ gocontext.Context, _ *containerd.Client, _ *containers.Container, s *specs.Spec) error {
 		env := context.StringSlice("env")
@@ -42,10 +41,84 @@ func withMounts(context *cli.Context) containerd.SpecOpts {
 	}
 }
 
-var runCommand = cli.Command{
+// parseMountFlag parses a mount string in the form "type=foo,source=/path,destination=/target,options=rbind:rw"
+func parseMountFlag(m string) (specs.Mount, error) {
+	mount := specs.Mount{}
+	r := csv.NewReader(strings.NewReader(m))
+
+	fields, err := r.Read()
+	if err != nil {
+		return mount, err
+	}
+
+	for _, field := range fields {
+		v := strings.Split(field, "=")
+		if len(v) != 2 {
+			return mount, fmt.Errorf("invalid mount specification: expected key=val")
+		}
+
+		key := v[0]
+		val := v[1]
+		switch key {
+		case "type":
+			mount.Type = val
+		case "source", "src":
+			mount.Source = val
+		case "destination", "dst":
+			mount.Destination = val
+		case "options":
+			mount.Options = strings.Split(val, ":")
+		default:
+			return mount, fmt.Errorf("mount option %q not supported", key)
+		}
+	}
+
+	return mount, nil
+}
+
+// replaceOrAppendEnvValues returns the defaults with the overrides either
+// replaced by env key or appended to the list
+func replaceOrAppendEnvValues(defaults, overrides []string) []string {
+	cache := make(map[string]int, len(defaults))
+	for i, e := range defaults {
+		parts := strings.SplitN(e, "=", 2)
+		cache[parts[0]] = i
+	}
+
+	for _, value := range overrides {
+		// Values w/o = means they want this env to be removed/unset.
+		if !strings.Contains(value, "=") {
+			if i, exists := cache[value]; exists {
+				defaults[i] = "" // Used to indicate it should be removed
+			}
+			continue
+		}
+
+		// Just do a normal set/update
+		parts := strings.SplitN(value, "=", 2)
+		if i, exists := cache[parts[0]]; exists {
+			defaults[i] = value
+		} else {
+			defaults = append(defaults, value)
+		}
+	}
+
+	// Now remove all entries that we want to "unset"
+	for i := 0; i < len(defaults); i++ {
+		if defaults[i] == "" {
+			defaults = append(defaults[:i], defaults[i+1:]...)
+			i--
+		}
+	}
+
+	return defaults
+}
+
+// Command runs a container
+var Command = cli.Command{
 	Name:      "run",
 	Usage:     "run a container",
-	ArgsUsage: "Image|RootFS ID [COMMAND] [ARG...]",
+	ArgsUsage: "[flags] Image|RootFS ID [COMMAND] [ARG...]",
 	Flags: append([]cli.Flag{
 		cli.BoolFlag{
 			Name:  "tty,t",
@@ -125,7 +198,7 @@ var runCommand = cli.Command{
 		if context.Bool("rm") && !detach {
 			defer container.Delete(ctx, containerd.WithSnapshotCleanup)
 		}
-		task, err := newTask(ctx, client, container, context.String("checkpoint"), tty, context.Bool("null-io"))
+		task, err := tasks.NewTask(ctx, client, container, context.String("checkpoint"), tty, context.Bool("null-io"))
 		if err != nil {
 			return err
 		}
@@ -151,7 +224,7 @@ var runCommand = cli.Command{
 			return nil
 		}
 		if tty {
-			if err := handleConsoleResize(ctx, task, con); err != nil {
+			if err := tasks.HandleConsoleResize(ctx, task, con); err != nil {
 				logrus.WithError(err).Error("console resize")
 			}
 		} else {
diff --git a/cmd/ctr/run_unix.go b/cmd/ctr/commands/run/run_unix.go
similarity index 62%
rename from cmd/ctr/run_unix.go
rename to cmd/ctr/commands/run/run_unix.go
index a2a8574ae..ee518abd5 100644
--- a/cmd/ctr/run_unix.go
+++ b/cmd/ctr/commands/run/run_unix.go
@@ -1,56 +1,23 @@
 // +build !windows
 
-package main
+package run
 
 import (
 	gocontext "context"
-	"os"
-	"os/signal"
 
-	"golang.org/x/sys/unix"
-
-	"github.com/containerd/console"
 	"github.com/containerd/containerd"
 	"github.com/containerd/containerd/cmd/ctr/commands"
 	specs "github.com/opencontainers/runtime-spec/specs-go"
-	"github.com/pkg/errors"
-	"github.com/sirupsen/logrus"
 	"github.com/urfave/cli"
 )
 
 func init() {
-	runCommand.Flags = append(runCommand.Flags, cli.BoolFlag{
+	Command.Flags = append(Command.Flags, cli.BoolFlag{
 		Name:  "rootfs",
-		Usage: "use custom rootfs that is not managed by containerd snapshotter.",
+		Usage: "use custom rootfs that is not managed by containerd snapshotter",
 	})
 }
 
-func handleConsoleResize(ctx gocontext.Context, task resizer, con console.Console) error {
-	// do an initial resize of the console
-	size, err := con.Size()
-	if err != nil {
-		return err
-	}
-	if err := task.Resize(ctx, uint32(size.Width), uint32(size.Height)); err != nil {
-		logrus.WithError(err).Error("resize pty")
-	}
-	s := make(chan os.Signal, 16)
-	signal.Notify(s, unix.SIGWINCH)
-	go func() {
-		for range s {
-			size, err := con.Size()
-			if err != nil {
-				logrus.WithError(err).Error("get pty size")
-				continue
-			}
-			if err := task.Resize(ctx, uint32(size.Width), uint32(size.Height)); err != nil {
-				logrus.WithError(err).Error("resize pty")
-			}
-		}
-	}()
-	return nil
-}
-
 func withTTY() containerd.SpecOpts {
 	return containerd.WithTTY
 }
@@ -115,24 +82,3 @@ func newContainer(ctx gocontext.Context, client *containerd.Client, context *cli
 	cOpts = append([]containerd.NewContainerOpts{containerd.WithNewSpec(opts...)}, cOpts...)
 	return client.NewContainer(ctx, id, cOpts...)
 }
-
-func newTask(ctx gocontext.Context, client *containerd.Client, container containerd.Container, checkpoint string, tty, nullIO bool) (containerd.Task, error) {
-	if checkpoint == "" {
-		io := containerd.Stdio
-		if tty {
-			io = containerd.StdioTerminal
-		}
-		if nullIO {
-			if tty {
-				return nil, errors.New("tty and null-io cannot be used together")
-			}
-			io = containerd.NullIO
-		}
-		return container.NewTask(ctx, io)
-	}
-	im, err := client.GetImage(ctx, checkpoint)
-	if err != nil {
-		return nil, err
-	}
-	return container.NewTask(ctx, containerd.Stdio, containerd.WithTaskCheckpoint(im))
-}
diff --git a/cmd/ctr/run_windows.go b/cmd/ctr/commands/run/run_windows.go
similarity index 67%
rename from cmd/ctr/run_windows.go
rename to cmd/ctr/commands/run/run_windows.go
index b50c8dbf4..5a004b65f 100644
--- a/cmd/ctr/run_windows.go
+++ b/cmd/ctr/commands/run/run_windows.go
@@ -1,15 +1,13 @@
-package main
+package run
 
 import (
 	gocontext "context"
-	"time"
 
 	"github.com/containerd/console"
 	"github.com/containerd/containerd"
 	"github.com/containerd/containerd/cmd/ctr/commands"
 	"github.com/containerd/containerd/containers"
 	"github.com/containerd/containerd/errdefs"
-	"github.com/containerd/containerd/log"
 	specs "github.com/opencontainers/runtime-spec/specs-go"
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
@@ -19,7 +17,7 @@ import (
 const pipeRoot = `\\.\pipe`
 
 func init() {
-	runCommand.Flags = append(runCommand.Flags, cli.StringSliceFlag{
+	Command.Flags = append(Command.Flags, cli.StringSliceFlag{
 		Name:  "layer",
 		Usage: "HCSSHIM Layers to be used",
 	})
@@ -36,34 +34,6 @@ func withLayers(context *cli.Context) containerd.SpecOpts {
 	}
 }
 
-func handleConsoleResize(ctx gocontext.Context, task resizer, con console.Console) error {
-	// do an initial resize of the console
-	size, err := con.Size()
-	if err != nil {
-		return err
-	}
-	go func() {
-		prevSize := size
-		for {
-			time.Sleep(time.Millisecond * 250)
-
-			size, err := con.Size()
-			if err != nil {
-				log.G(ctx).WithError(err).Error("get pty size")
-				continue
-			}
-
-			if size.Width != prevSize.Width || size.Height != prevSize.Height {
-				if err := task.Resize(ctx, uint32(size.Width), uint32(size.Height)); err != nil {
-					logrus.WithError(err).Error("resize pty")
-				}
-				prevSize = size
-			}
-		}
-	}()
-	return nil
-}
-
 func withTTY(terminal bool) containerd.SpecOpts {
 	if !terminal {
 		return func(ctx gocontext.Context, client *containerd.Client, c *containers.Container, s *specs.Spec) error {
@@ -117,17 +87,3 @@ func newContainer(ctx gocontext.Context, client *containerd.Client, context *cli
 		// TODO(mlaventure): containerd.WithImage(image),
 	)
 }
-
-func newTask(ctx gocontext.Context, client *containerd.Client, container containerd.Container, _ string, tty, nullIO bool) (containerd.Task, error) {
-	io := containerd.Stdio
-	if tty {
-		io = containerd.StdioTerminal
-	}
-	if nullIO {
-		if tty {
-			return nil, errors.New("tty and null-io cannot be used together")
-		}
-		io = containerd.NullIO
-	}
-	return container.NewTask(ctx, io)
-}
diff --git a/cmd/ctr/utils_unix.go b/cmd/ctr/commands/shim/io_unix.go
similarity index 98%
rename from cmd/ctr/utils_unix.go
rename to cmd/ctr/commands/shim/io_unix.go
index 69967f6f3..f328f006b 100644
--- a/cmd/ctr/utils_unix.go
+++ b/cmd/ctr/commands/shim/io_unix.go
@@ -1,6 +1,6 @@
 // +build !windows
 
-package main
+package shim
 
 import (
 	gocontext "context"
diff --git a/cmd/ctr/utils_windows.go b/cmd/ctr/commands/shim/io_windows.go
similarity index 99%
rename from cmd/ctr/utils_windows.go
rename to cmd/ctr/commands/shim/io_windows.go
index ac364f792..4125b3fdd 100644
--- a/cmd/ctr/utils_windows.go
+++ b/cmd/ctr/commands/shim/io_windows.go
@@ -1,4 +1,4 @@
-package main
+package shim
 
 import (
 	"io"
diff --git a/cmd/ctr/shim.go b/cmd/ctr/commands/shim/shim.go
similarity index 70%
rename from cmd/ctr/shim.go
rename to cmd/ctr/commands/shim/shim.go
index c3145cbb4..63428c99c 100644
--- a/cmd/ctr/shim.go
+++ b/cmd/ctr/commands/shim/shim.go
@@ -1,6 +1,6 @@
 // +build !windows
 
-package main
+package shim
 
 import (
 	"fmt"
@@ -45,7 +45,8 @@ var fifoFlags = []cli.Flag{
 	},
 }
 
-var shimCommand = cli.Command{
+// Command is the cli command for interacting with a shim
+var Command = cli.Command{
 	Name:  "shim",
 	Usage: "interact with a shim directly",
 	Flags: []cli.Flag{
@@ -55,89 +56,14 @@ var shimCommand = cli.Command{
 		},
 	},
 	Subcommands: []cli.Command{
-		shimCreateCommand,
-		shimStartCommand,
-		shimDeleteCommand,
-		shimStateCommand,
-		shimExecCommand,
+		deleteCommand,
+		execCommand,
+		startCommand,
+		stateCommand,
 	},
 }
 
-var shimCreateCommand = cli.Command{
-	Name:  "create",
-	Usage: "create a container with a shim",
-	Flags: append(fifoFlags,
-		cli.StringFlag{
-			Name:  "bundle",
-			Usage: "bundle path for the container",
-		},
-		cli.StringFlag{
-			Name:  "runtime",
-			Value: "runc",
-			Usage: "runtime to use for the container",
-		},
-		cli.BoolFlag{
-			Name:  "attach,a",
-			Usage: "stay attached to the container and open the fifos",
-		},
-	),
-	Action: func(context *cli.Context) error {
-		var (
-			id  = context.Args().First()
-			ctx = gocontext.Background()
-		)
-
-		if id == "" {
-			return errors.New("container id must be provided")
-		}
-		service, err := getShimService(context)
-		if err != nil {
-			return err
-		}
-		tty := context.Bool("tty")
-		wg, err := prepareStdio(context.String("stdin"), context.String("stdout"), context.String("stderr"), tty)
-		if err != nil {
-			return err
-		}
-		r, err := service.Create(ctx, &shim.CreateTaskRequest{
-			ID:       id,
-			Bundle:   context.String("bundle"),
-			Runtime:  context.String("runtime"),
-			Stdin:    context.String("stdin"),
-			Stdout:   context.String("stdout"),
-			Stderr:   context.String("stderr"),
-			Terminal: tty,
-		})
-		if err != nil {
-			return err
-		}
-		fmt.Printf("container created with id %s and pid %d\n", id, r.Pid)
-		if context.Bool("attach") {
-			if tty {
-				current := console.Current()
-				defer current.Reset()
-				if err := current.SetRaw(); err != nil {
-					return err
-				}
-				size, err := current.Size()
-				if err != nil {
-					return err
-				}
-				if _, err := service.ResizePty(ctx, &shim.ResizePtyRequest{
-					ID:     id,
-					Width:  uint32(size.Width),
-					Height: uint32(size.Height),
-				}); err != nil {
-					return err
-				}
-			}
-			wg.Wait()
-		}
-		return nil
-	},
-}
-
-var shimStartCommand = cli.Command{
+var startCommand = cli.Command{
 	Name:  "start",
 	Usage: "start a container with a shim",
 	Action: func(context *cli.Context) error {
@@ -152,7 +78,7 @@ var shimStartCommand = cli.Command{
 	},
 }
 
-var shimDeleteCommand = cli.Command{
+var deleteCommand = cli.Command{
 	Name:  "delete",
 	Usage: "delete a container with a shim",
 	Action: func(context *cli.Context) error {
@@ -169,7 +95,7 @@ var shimDeleteCommand = cli.Command{
 	},
 }
 
-var shimStateCommand = cli.Command{
+var stateCommand = cli.Command{
 	Name:  "state",
 	Usage: "get the state of all the processes of the shim",
 	Action: func(context *cli.Context) error {
@@ -188,7 +114,7 @@ var shimStateCommand = cli.Command{
 	},
 }
 
-var shimExecCommand = cli.Command{
+var execCommand = cli.Command{
 	Name:  "exec",
 	Usage: "exec a new process in the shim's container",
 	Flags: append(fifoFlags,
diff --git a/cmd/ctr/commands/signals_linux.go b/cmd/ctr/commands/signal_map_linux.go
similarity index 100%
rename from cmd/ctr/commands/signals_linux.go
rename to cmd/ctr/commands/signal_map_linux.go
diff --git a/cmd/ctr/commands/signals_unix.go b/cmd/ctr/commands/signal_map_unix.go
similarity index 100%
rename from cmd/ctr/commands/signals_unix.go
rename to cmd/ctr/commands/signal_map_unix.go
diff --git a/cmd/ctr/commands/signals_windows.go b/cmd/ctr/commands/signal_map_windows.go
similarity index 100%
rename from cmd/ctr/commands/signals_windows.go
rename to cmd/ctr/commands/signal_map_windows.go
diff --git a/cmd/ctr/commands/snapshot/snapshot.go b/cmd/ctr/commands/snapshot/snapshot.go
index 9def7a819..734871823 100644
--- a/cmd/ctr/commands/snapshot/snapshot.go
+++ b/cmd/ctr/commands/snapshot/snapshot.go
@@ -23,17 +23,17 @@ var Command = cli.Command{
 	Usage: "manage snapshots",
 	Flags: commands.SnapshotterFlags,
 	Subcommands: cli.Commands{
-		listCommand,
-		usageCommand,
-		removeCommand,
-		prepareCommand,
-		viewCommand,
-		treeCommand,
-		mountCommand,
 		commitCommand,
 		infoCommand,
+		listCommand,
+		mountCommand,
+		prepareCommand,
+		removeCommand,
 		setLabelCommand,
+		treeCommand,
 		unpackCommand,
+		usageCommand,
+		viewCommand,
 	},
 }
 
diff --git a/cmd/ctr/attach.go b/cmd/ctr/commands/tasks/attach.go
similarity index 92%
rename from cmd/ctr/attach.go
rename to cmd/ctr/commands/tasks/attach.go
index f1af6ab30..22e6fb90e 100644
--- a/cmd/ctr/attach.go
+++ b/cmd/ctr/commands/tasks/attach.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"os"
@@ -10,7 +10,7 @@ import (
 	"github.com/urfave/cli"
 )
 
-var taskAttachCommand = cli.Command{
+var attachCommand = cli.Command{
 	Name:      "attach",
 	Usage:     "attach to the IO of a running container",
 	ArgsUsage: "CONTAINER",
@@ -51,7 +51,7 @@ var taskAttachCommand = cli.Command{
 		}
 
 		if tty {
-			if err := handleConsoleResize(ctx, task, con); err != nil {
+			if err := HandleConsoleResize(ctx, task, con); err != nil {
 				logrus.WithError(err).Error("console resize")
 			}
 		} else {
diff --git a/cmd/ctr/checkpoint.go b/cmd/ctr/commands/tasks/checkpoint.go
similarity index 92%
rename from cmd/ctr/checkpoint.go
rename to cmd/ctr/commands/tasks/checkpoint.go
index 6f4c2fdd9..6915caf84 100644
--- a/cmd/ctr/checkpoint.go
+++ b/cmd/ctr/commands/tasks/checkpoint.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"fmt"
@@ -9,10 +9,10 @@ import (
 	"github.com/urfave/cli"
 )
 
-var taskCheckpointCommand = cli.Command{
+var checkpointCommand = cli.Command{
 	Name:      "checkpoint",
 	Usage:     "checkpoint a container",
-	ArgsUsage: "CONTAINER",
+	ArgsUsage: "[flags] CONTAINER",
 	Flags: []cli.Flag{
 		cli.BoolFlag{
 			Name:  "exit",
diff --git a/cmd/ctr/task_delete.go b/cmd/ctr/commands/tasks/delete.go
similarity index 93%
rename from cmd/ctr/task_delete.go
rename to cmd/ctr/commands/tasks/delete.go
index dbae378c1..ba60fe625 100644
--- a/cmd/ctr/task_delete.go
+++ b/cmd/ctr/commands/tasks/delete.go
@@ -1,11 +1,11 @@
-package main
+package tasks
 
 import (
 	"github.com/containerd/containerd/cmd/ctr/commands"
 	"github.com/urfave/cli"
 )
 
-var taskDeleteCommand = cli.Command{
+var deleteCommand = cli.Command{
 	Name:      "delete",
 	Usage:     "delete a task",
 	ArgsUsage: "CONTAINER",
diff --git a/cmd/ctr/exec.go b/cmd/ctr/commands/tasks/exec.go
similarity index 93%
rename from cmd/ctr/exec.go
rename to cmd/ctr/commands/tasks/exec.go
index 65659827d..f3303ade2 100644
--- a/cmd/ctr/exec.go
+++ b/cmd/ctr/commands/tasks/exec.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"errors"
@@ -11,10 +11,10 @@ import (
 )
 
 //TODO:(jessvalarezo) exec-id is optional here, update to required arg
-var taskExecCommand = cli.Command{
+var execCommand = cli.Command{
 	Name:      "exec",
 	Usage:     "execute additional processes in an existing container",
-	ArgsUsage: "CONTAINER CMD [ARG...]",
+	ArgsUsage: "[flags] CONTAINER CMD [ARG...]",
 	Flags: []cli.Flag{
 		cli.StringFlag{
 			Name:  "cwd",
@@ -84,7 +84,7 @@ var taskExecCommand = cli.Command{
 			}
 		}
 		if tty {
-			if err := handleConsoleResize(ctx, process, con); err != nil {
+			if err := HandleConsoleResize(ctx, process, con); err != nil {
 				logrus.WithError(err).Error("console resize")
 			}
 		} else {
diff --git a/cmd/ctr/kill.go b/cmd/ctr/commands/tasks/kill.go
similarity index 94%
rename from cmd/ctr/kill.go
rename to cmd/ctr/commands/tasks/kill.go
index 159f409ee..5b1a5f427 100644
--- a/cmd/ctr/kill.go
+++ b/cmd/ctr/commands/tasks/kill.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"github.com/containerd/containerd/cmd/ctr/commands"
@@ -8,10 +8,10 @@ import (
 
 // TODO:(jessvalarezo) the pid flag is not used here
 // update to be able to signal given pid
-var taskKillCommand = cli.Command{
+var killCommand = cli.Command{
 	Name:      "kill",
 	Usage:     "signal a container (default: SIGTERM)",
-	ArgsUsage: "CONTAINER",
+	ArgsUsage: "[flags] CONTAINER",
 	Flags: []cli.Flag{
 		cli.StringFlag{
 			Name:  "signal, s",
diff --git a/cmd/ctr/task.go b/cmd/ctr/commands/tasks/list.go
similarity index 68%
rename from cmd/ctr/task.go
rename to cmd/ctr/commands/tasks/list.go
index 243394380..0ae3def51 100644
--- a/cmd/ctr/task.go
+++ b/cmd/ctr/commands/tasks/list.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"fmt"
@@ -10,28 +10,11 @@ import (
 	"github.com/urfave/cli"
 )
 
-var tasksCommand = cli.Command{
-	Name:    "tasks",
-	Usage:   "manage tasks",
-	Aliases: []string{"t"},
-	Subcommands: []cli.Command{
-		taskAttachCommand,
-		taskCheckpointCommand,
-		taskExecCommand,
-		taskKillCommand,
-		taskPauseCommand,
-		taskPsCommand,
-		taskResumeCommand,
-		taskStartCommand,
-		taskDeleteCommand,
-		taskListCommand,
-	},
-}
-
-var taskListCommand = cli.Command{
-	Name:    "list",
-	Usage:   "list tasks",
-	Aliases: []string{"ls"},
+var listCommand = cli.Command{
+	Name:      "list",
+	Usage:     "list tasks",
+	Aliases:   []string{"ls"},
+	ArgsUsage: "[flags]",
 	Flags: []cli.Flag{
 		cli.BoolFlag{
 			Name:  "quiet, q",
diff --git a/cmd/ctr/pause.go b/cmd/ctr/commands/tasks/pause.go
similarity index 91%
rename from cmd/ctr/pause.go
rename to cmd/ctr/commands/tasks/pause.go
index 92944f67e..3f46456a1 100644
--- a/cmd/ctr/pause.go
+++ b/cmd/ctr/commands/tasks/pause.go
@@ -1,11 +1,11 @@
-package main
+package tasks
 
 import (
 	"github.com/containerd/containerd/cmd/ctr/commands"
 	"github.com/urfave/cli"
 )
 
-var taskPauseCommand = cli.Command{
+var pauseCommand = cli.Command{
 	Name:      "pause",
 	Usage:     "pause an existing container",
 	ArgsUsage: "CONTAINER",
diff --git a/cmd/ctr/ps.go b/cmd/ctr/commands/tasks/ps.go
similarity index 96%
rename from cmd/ctr/ps.go
rename to cmd/ctr/commands/tasks/ps.go
index 058dec473..f371e4458 100644
--- a/cmd/ctr/ps.go
+++ b/cmd/ctr/commands/tasks/ps.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"fmt"
@@ -11,7 +11,7 @@ import (
 	"github.com/urfave/cli"
 )
 
-var taskPsCommand = cli.Command{
+var psCommand = cli.Command{
 	Name:      "ps",
 	Usage:     "list processes for container",
 	ArgsUsage: "CONTAINER",
diff --git a/cmd/ctr/resume.go b/cmd/ctr/commands/tasks/resume.go
similarity index 91%
rename from cmd/ctr/resume.go
rename to cmd/ctr/commands/tasks/resume.go
index 92d860711..d1680edd3 100644
--- a/cmd/ctr/resume.go
+++ b/cmd/ctr/commands/tasks/resume.go
@@ -1,11 +1,11 @@
-package main
+package tasks
 
 import (
 	"github.com/containerd/containerd/cmd/ctr/commands"
 	"github.com/urfave/cli"
 )
 
-var taskResumeCommand = cli.Command{
+var resumeCommand = cli.Command{
 	Name:      "resume",
 	Usage:     "resume a paused container",
 	ArgsUsage: "CONTAINER",
diff --git a/cmd/ctr/start.go b/cmd/ctr/commands/tasks/start.go
similarity index 90%
rename from cmd/ctr/start.go
rename to cmd/ctr/commands/tasks/start.go
index 9f37af9ee..df09a9b9a 100644
--- a/cmd/ctr/start.go
+++ b/cmd/ctr/commands/tasks/start.go
@@ -1,4 +1,4 @@
-package main
+package tasks
 
 import (
 	"github.com/containerd/console"
@@ -8,7 +8,7 @@ import (
 	"github.com/urfave/cli"
 )
 
-var taskStartCommand = cli.Command{
+var startCommand = cli.Command{
 	Name:      "start",
 	Usage:     "start a container that have been created",
 	ArgsUsage: "CONTAINER",
@@ -43,7 +43,7 @@ var taskStartCommand = cli.Command{
 
 		tty := spec.Process.Terminal
 
-		task, err := newTask(ctx, client, container, "", tty, context.Bool("null-io"))
+		task, err := NewTask(ctx, client, container, "", tty, context.Bool("null-io"))
 		if err != nil {
 			return err
 		}
@@ -66,7 +66,7 @@ var taskStartCommand = cli.Command{
 			return err
 		}
 		if tty {
-			if err := handleConsoleResize(ctx, task, con); err != nil {
+			if err := HandleConsoleResize(ctx, task, con); err != nil {
 				logrus.WithError(err).Error("console resize")
 			}
 		} else {
diff --git a/cmd/ctr/commands/tasks/tasks.go b/cmd/ctr/commands/tasks/tasks.go
new file mode 100644
index 000000000..356e3e4fe
--- /dev/null
+++ b/cmd/ctr/commands/tasks/tasks.go
@@ -0,0 +1,30 @@
+package tasks
+
+import (
+	gocontext "context"
+
+	"github.com/urfave/cli"
+)
+
+type resizer interface {
+	Resize(ctx gocontext.Context, w, h uint32) error
+}
+
+// Command is the cli command for managing tasks
+var Command = cli.Command{
+	Name:    "tasks",
+	Usage:   "manage tasks",
+	Aliases: []string{"t"},
+	Subcommands: []cli.Command{
+		attachCommand,
+		checkpointCommand,
+		deleteCommand,
+		execCommand,
+		listCommand,
+		killCommand,
+		pauseCommand,
+		psCommand,
+		resumeCommand,
+		startCommand,
+	},
+}
diff --git a/cmd/ctr/commands/tasks/tasks_unix.go b/cmd/ctr/commands/tasks/tasks_unix.go
new file mode 100644
index 000000000..edda13b31
--- /dev/null
+++ b/cmd/ctr/commands/tasks/tasks_unix.go
@@ -0,0 +1,64 @@
+// +build !windows
+
+package tasks
+
+import (
+	gocontext "context"
+	"os"
+	"os/signal"
+
+	"github.com/containerd/console"
+	"github.com/containerd/containerd"
+	"github.com/containerd/containerd/log"
+	"github.com/pkg/errors"
+	"golang.org/x/sys/unix"
+)
+
+// HandleConsoleResize resizes the console
+func HandleConsoleResize(ctx gocontext.Context, task resizer, con console.Console) error {
+	// do an initial resize of the console
+	size, err := con.Size()
+	if err != nil {
+		return err
+	}
+	if err := task.Resize(ctx, uint32(size.Width), uint32(size.Height)); err != nil {
+		log.G(ctx).WithError(err).Error("resize pty")
+	}
+	s := make(chan os.Signal, 16)
+	signal.Notify(s, unix.SIGWINCH)
+	go func() {
+		for range s {
+			size, err := con.Size()
+			if err != nil {
+				log.G(ctx).WithError(err).Error("get pty size")
+				continue
+			}
+			if err := task.Resize(ctx, uint32(size.Width), uint32(size.Height)); err != nil {
+				log.G(ctx).WithError(err).Error("resize pty")
+			}
+		}
+	}()
+	return nil
+}
+
+// NewTask creates a new task
+func NewTask(ctx gocontext.Context, client *containerd.Client, container containerd.Container, checkpoint string, tty, nullIO bool) (containerd.Task, error) {
+	if checkpoint == "" {
+		io := containerd.Stdio
+		if tty {
+			io = containerd.StdioTerminal
+		}
+		if nullIO {
+			if tty {
+				return nil, errors.New("tty and null-io cannot be used together")
+			}
+			io = containerd.NullIO
+		}
+		return container.NewTask(ctx, io)
+	}
+	im, err := client.GetImage(ctx, checkpoint)
+	if err != nil {
+		return nil, err
+	}
+	return container.NewTask(ctx, containerd.Stdio, containerd.WithTaskCheckpoint(im))
+}
diff --git a/cmd/ctr/commands/tasks/tasks_windows.go b/cmd/ctr/commands/tasks/tasks_windows.go
new file mode 100644
index 000000000..dda2fb1d6
--- /dev/null
+++ b/cmd/ctr/commands/tasks/tasks_windows.go
@@ -0,0 +1,55 @@
+package tasks
+
+import (
+	gocontext "context"
+	"time"
+
+	"github.com/containerd/console"
+	"github.com/containerd/containerd"
+	"github.com/containerd/containerd/log"
+	"github.com/pkg/errors"
+)
+
+// HandleConsoleResize resizes the console
+func HandleConsoleResize(ctx gocontext.Context, task resizer, con console.Console) error {
+	// do an initial resize of the console
+	size, err := con.Size()
+	if err != nil {
+		return err
+	}
+	go func() {
+		prevSize := size
+		for {
+			time.Sleep(time.Millisecond * 250)
+
+			size, err := con.Size()
+			if err != nil {
+				log.G(ctx).WithError(err).Error("get pty size")
+				continue
+			}
+
+			if size.Width != prevSize.Width || size.Height != prevSize.Height {
+				if err := task.Resize(ctx, uint32(size.Width), uint32(size.Height)); err != nil {
+					log.G(ctx).WithError(err).Error("resize pty")
+				}
+				prevSize = size
+			}
+		}
+	}()
+	return nil
+}
+
+// NewTask creates a new task
+func NewTask(ctx gocontext.Context, client *containerd.Client, container containerd.Container, _ string, tty, nullIO bool) (containerd.Task, error) {
+	io := containerd.Stdio
+	if tty {
+		io = containerd.StdioTerminal
+	}
+	if nullIO {
+		if tty {
+			return nil, errors.New("tty and null-io cannot be used together")
+		}
+		io = containerd.NullIO
+	}
+	return container.NewTask(ctx, io)
+}
diff --git a/cmd/ctr/main.go b/cmd/ctr/main.go
index f3e547324..3b96a0413 100644
--- a/cmd/ctr/main.go
+++ b/cmd/ctr/main.go
@@ -12,7 +12,10 @@ import (
 	"github.com/containerd/containerd/cmd/ctr/commands/images"
 	namespacesCmd "github.com/containerd/containerd/cmd/ctr/commands/namespaces"
 	"github.com/containerd/containerd/cmd/ctr/commands/plugins"
+	"github.com/containerd/containerd/cmd/ctr/commands/pprof"
+	"github.com/containerd/containerd/cmd/ctr/commands/run"
 	"github.com/containerd/containerd/cmd/ctr/commands/snapshot"
+	"github.com/containerd/containerd/cmd/ctr/commands/tasks"
 	versionCmd "github.com/containerd/containerd/cmd/ctr/commands/version"
 	"github.com/containerd/containerd/namespaces"
 	"github.com/containerd/containerd/server"
@@ -79,10 +82,10 @@ containerd CLI
 		events.Command,
 		images.Command,
 		namespacesCmd.Command,
-		pprofCommand,
-		runCommand,
+		pprof.Command,
+		run.Command,
 		snapshot.Command,
-		tasksCommand,
+		tasks.Command,
 	}, extraCmds...)
 	app.Before = func(context *cli.Context) error {
 		if context.GlobalBool("debug") {
diff --git a/cmd/ctr/main_unix.go b/cmd/ctr/main_unix.go
index a8c51956c..cd25dc213 100644
--- a/cmd/ctr/main_unix.go
+++ b/cmd/ctr/main_unix.go
@@ -2,6 +2,8 @@
 
 package main
 
+import "github.com/containerd/containerd/cmd/ctr/commands/shim"
+
 func init() {
-	extraCmds = append(extraCmds, shimCommand)
+	extraCmds = append(extraCmds, shim.Command)
 }
diff --git a/cmd/ctr/utils.go b/cmd/ctr/utils.go
deleted file mode 100644
index ad00b40ef..000000000
--- a/cmd/ctr/utils.go
+++ /dev/null
@@ -1,82 +0,0 @@
-package main
-
-import (
-	"encoding/csv"
-	"fmt"
-	"strings"
-
-	specs "github.com/opencontainers/runtime-spec/specs-go"
-)
-
-// parseMountFlag parses a mount string in the form "type=foo,source=/path,destination=/target,options=rbind:rw"
-func parseMountFlag(m string) (specs.Mount, error) {
-	mount := specs.Mount{}
-	r := csv.NewReader(strings.NewReader(m))
-
-	fields, err := r.Read()
-	if err != nil {
-		return mount, err
-	}
-
-	for _, field := range fields {
-		v := strings.Split(field, "=")
-		if len(v) != 2 {
-			return mount, fmt.Errorf("invalid mount specification: expected key=val")
-		}
-
-		key := v[0]
-		val := v[1]
-		switch key {
-		case "type":
-			mount.Type = val
-		case "source", "src":
-			mount.Source = val
-		case "destination", "dst":
-			mount.Destination = val
-		case "options":
-			mount.Options = strings.Split(val, ":")
-		default:
-			return mount, fmt.Errorf("mount option %q not supported", key)
-		}
-	}
-
-	return mount, nil
-}
-
-// replaceOrAppendEnvValues returns the defaults with the overrides either
-// replaced by env key or appended to the list
-func replaceOrAppendEnvValues(defaults, overrides []string) []string {
-	cache := make(map[string]int, len(defaults))
-	for i, e := range defaults {
-		parts := strings.SplitN(e, "=", 2)
-		cache[parts[0]] = i
-	}
-
-	for _, value := range overrides {
-		// Values w/o = means they want this env to be removed/unset.
-		if !strings.Contains(value, "=") {
-			if i, exists := cache[value]; exists {
-				defaults[i] = "" // Used to indicate it should be removed
-			}
-			continue
-		}
-
-		// Just do a normal set/update
-		parts := strings.SplitN(value, "=", 2)
-		if i, exists := cache[parts[0]]; exists {
-			defaults[i] = value
-		} else {
-			defaults = append(defaults, value)
-		}
-	}
-
-	// Now remove all entries that we want to "unset"
-	for i := 0; i < len(defaults); i++ {
-		if defaults[i] == "" {
-			defaults = append(defaults[:i], defaults[i+1:]...)
-			i--
-		}
-	}
-
-	return defaults
-}