diff --git a/cli/command/builder/client_test.go b/cli/command/builder/client_test.go
new file mode 100644
index 0000000000..6214dcf30d
--- /dev/null
+++ b/cli/command/builder/client_test.go
@@ -0,0 +1,20 @@
+package builder
+
+import (
+	"context"
+
+	"github.com/docker/docker/api/types"
+	"github.com/docker/docker/client"
+)
+
+type fakeClient struct {
+	client.Client
+	builderPruneFunc func(ctx context.Context, opts types.BuildCachePruneOptions) (*types.BuildCachePruneReport, error)
+}
+
+func (c *fakeClient) BuildCachePrune(ctx context.Context, opts types.BuildCachePruneOptions) (*types.BuildCachePruneReport, error) {
+	if c.builderPruneFunc != nil {
+		return c.builderPruneFunc(ctx, opts)
+	}
+	return nil, nil
+}
diff --git a/cli/command/builder/prune.go b/cli/command/builder/prune.go
index 6286218cac..cd453cbbc0 100644
--- a/cli/command/builder/prune.go
+++ b/cli/command/builder/prune.go
@@ -66,8 +66,10 @@ func runPrune(ctx context.Context, dockerCli command.Cli, options pruneOptions)
 	if options.all {
 		warning = allCacheWarning
 	}
-	if !options.force && !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), warning) {
-		return 0, "", nil
+	if !options.force {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), warning); !r || err != nil {
+			return 0, "", err
+		}
 	}
 
 	report, err := dockerCli.Client().BuildCachePrune(ctx, types.BuildCachePruneOptions{
diff --git a/cli/command/builder/prune_test.go b/cli/command/builder/prune_test.go
new file mode 100644
index 0000000000..57ea995445
--- /dev/null
+++ b/cli/command/builder/prune_test.go
@@ -0,0 +1,28 @@
+package builder
+
+import (
+	"context"
+	"errors"
+	"testing"
+
+	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/internal/test"
+	"github.com/docker/docker/api/types"
+	"gotest.tools/v3/assert"
+)
+
+func TestBuilderPromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		builderPruneFunc: func(ctx context.Context, opts types.BuildCachePruneOptions) (*types.BuildCachePruneReport, error) {
+			return nil, errors.New("fakeClient builderPruneFunc should not be called")
+		},
+	})
+	cmd := NewPruneCommand(cli)
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+}
diff --git a/cli/command/container/client_test.go b/cli/command/container/client_test.go
index 4b17fb3ca9..c45f34040f 100644
--- a/cli/command/container/client_test.go
+++ b/cli/command/container/client_test.go
@@ -6,6 +6,7 @@ import (
 
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/api/types/container"
+	"github.com/docker/docker/api/types/filters"
 	"github.com/docker/docker/api/types/image"
 	"github.com/docker/docker/api/types/network"
 	"github.com/docker/docker/api/types/system"
@@ -35,6 +36,7 @@ type fakeClient struct {
 	containerExecResizeFunc func(id string, options container.ResizeOptions) error
 	containerRemoveFunc     func(ctx context.Context, containerID string, options container.RemoveOptions) error
 	containerKillFunc       func(ctx context.Context, containerID, signal string) error
+	containerPruneFunc      func(ctx context.Context, pruneFilters filters.Args) (types.ContainersPruneReport, error)
 	Version                 string
 }
 
@@ -164,3 +166,10 @@ func (f *fakeClient) ContainerKill(ctx context.Context, containerID, signal stri
 	}
 	return nil
 }
+
+func (f *fakeClient) ContainersPrune(ctx context.Context, pruneFilters filters.Args) (types.ContainersPruneReport, error) {
+	if f.containerPruneFunc != nil {
+		return f.containerPruneFunc(ctx, pruneFilters)
+	}
+	return types.ContainersPruneReport{}, nil
+}
diff --git a/cli/command/container/prune.go b/cli/command/container/prune.go
index 0db41092e8..583473fac7 100644
--- a/cli/command/container/prune.go
+++ b/cli/command/container/prune.go
@@ -53,8 +53,10 @@ Are you sure you want to continue?`
 func runPrune(ctx context.Context, dockerCli command.Cli, options pruneOptions) (spaceReclaimed uint64, output string, err error) {
 	pruneFilters := command.PruneFilters(dockerCli, options.filter.Value())
 
-	if !options.force && !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), warning) {
-		return 0, "", nil
+	if !options.force {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), warning); !r || err != nil {
+			return 0, "", err
+		}
 	}
 
 	report, err := dockerCli.Client().ContainersPrune(ctx, pruneFilters)
diff --git a/cli/command/container/prune_test.go b/cli/command/container/prune_test.go
new file mode 100644
index 0000000000..05cf87b37b
--- /dev/null
+++ b/cli/command/container/prune_test.go
@@ -0,0 +1,29 @@
+package container
+
+import (
+	"context"
+	"testing"
+
+	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/internal/test"
+	"github.com/docker/docker/api/types"
+	"github.com/docker/docker/api/types/filters"
+	"github.com/pkg/errors"
+	"gotest.tools/v3/assert"
+)
+
+func TestContainerPrunePromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		containerPruneFunc: func(ctx context.Context, pruneFilters filters.Args) (types.ContainersPruneReport, error) {
+			return types.ContainersPruneReport{}, errors.New("fakeClient containerPruneFunc should not be called")
+		},
+	})
+	cmd := NewPruneCommand(cli)
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+}
diff --git a/cli/command/image/prune.go b/cli/command/image/prune.go
index 205a9dedb3..d627633cd5 100644
--- a/cli/command/image/prune.go
+++ b/cli/command/image/prune.go
@@ -67,8 +67,10 @@ func runPrune(ctx context.Context, dockerCli command.Cli, options pruneOptions)
 	if options.all {
 		warning = allImageWarning
 	}
-	if !options.force && !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), warning) {
-		return 0, "", nil
+	if !options.force {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), warning); !r || err != nil {
+			return 0, "", err
+		}
 	}
 
 	report, err := dockerCli.Client().ImagesPrune(ctx, pruneFilters)
diff --git a/cli/command/image/prune_test.go b/cli/command/image/prune_test.go
index a60c283c68..472f9f7f6d 100644
--- a/cli/command/image/prune_test.go
+++ b/cli/command/image/prune_test.go
@@ -1,10 +1,12 @@
 package image
 
 import (
+	"context"
 	"fmt"
 	"io"
 	"testing"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/docker/cli/internal/test"
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/api/types/filters"
@@ -101,3 +103,19 @@ func TestNewPruneCommandSuccess(t *testing.T) {
 		golden.Assert(t, cli.OutBuffer().String(), fmt.Sprintf("prune-command-success.%s.golden", tc.name))
 	}
 }
+
+func TestPrunePromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		imagesPruneFunc: func(pruneFilter filters.Args) (types.ImagesPruneReport, error) {
+			return types.ImagesPruneReport{}, errors.New("fakeClient imagesPruneFunc should not be called")
+		},
+	})
+	cmd := NewPruneCommand(cli)
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+}
diff --git a/cli/command/network/client_test.go b/cli/command/network/client_test.go
index 18c91e251d..d2fa4111fb 100644
--- a/cli/command/network/client_test.go
+++ b/cli/command/network/client_test.go
@@ -4,6 +4,7 @@ import (
 	"context"
 
 	"github.com/docker/docker/api/types"
+	"github.com/docker/docker/api/types/filters"
 	"github.com/docker/docker/api/types/network"
 	"github.com/docker/docker/client"
 )
@@ -15,6 +16,8 @@ type fakeClient struct {
 	networkDisconnectFunc func(ctx context.Context, networkID, container string, force bool) error
 	networkRemoveFunc     func(ctx context.Context, networkID string) error
 	networkListFunc       func(ctx context.Context, options types.NetworkListOptions) ([]types.NetworkResource, error)
+	networkPruneFunc      func(ctx context.Context, pruneFilters filters.Args) (types.NetworksPruneReport, error)
+	networkInspectFunc    func(ctx context.Context, networkID string, options types.NetworkInspectOptions) (types.NetworkResource, []byte, error)
 }
 
 func (c *fakeClient) NetworkCreate(ctx context.Context, name string, options types.NetworkCreate) (types.NetworkCreateResponse, error) {
@@ -52,6 +55,16 @@ func (c *fakeClient) NetworkRemove(ctx context.Context, networkID string) error
 	return nil
 }
 
-func (c *fakeClient) NetworkInspectWithRaw(context.Context, string, types.NetworkInspectOptions) (types.NetworkResource, []byte, error) {
+func (c *fakeClient) NetworkInspectWithRaw(ctx context.Context, networkID string, opts types.NetworkInspectOptions) (types.NetworkResource, []byte, error) {
+	if c.networkInspectFunc != nil {
+		return c.networkInspectFunc(ctx, networkID, opts)
+	}
 	return types.NetworkResource{}, nil, nil
 }
+
+func (c *fakeClient) NetworksPrune(ctx context.Context, pruneFilter filters.Args) (types.NetworksPruneReport, error) {
+	if c.networkPruneFunc != nil {
+		return c.networkPruneFunc(ctx, pruneFilter)
+	}
+	return types.NetworksPruneReport{}, nil
+}
diff --git a/cli/command/network/prune.go b/cli/command/network/prune.go
index f097878ac8..5f06770327 100644
--- a/cli/command/network/prune.go
+++ b/cli/command/network/prune.go
@@ -49,8 +49,10 @@ Are you sure you want to continue?`
 func runPrune(ctx context.Context, dockerCli command.Cli, options pruneOptions) (output string, err error) {
 	pruneFilters := command.PruneFilters(dockerCli, options.filter.Value())
 
-	if !options.force && !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), warning) {
-		return "", nil
+	if !options.force {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), warning); !r || err != nil {
+			return "", err
+		}
 	}
 
 	report, err := dockerCli.Client().NetworksPrune(ctx, pruneFilters)
diff --git a/cli/command/network/prune_test.go b/cli/command/network/prune_test.go
new file mode 100644
index 0000000000..9cf62a38e0
--- /dev/null
+++ b/cli/command/network/prune_test.go
@@ -0,0 +1,29 @@
+package network
+
+import (
+	"context"
+	"testing"
+
+	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/internal/test"
+	"github.com/docker/docker/api/types"
+	"github.com/docker/docker/api/types/filters"
+	"github.com/pkg/errors"
+	"gotest.tools/v3/assert"
+)
+
+func TestNetworkPrunePromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		networkPruneFunc: func(ctx context.Context, pruneFilters filters.Args) (types.NetworksPruneReport, error) {
+			return types.NetworksPruneReport{}, errors.New("fakeClient networkPruneFunc should not be called")
+		},
+	})
+	cmd := NewPruneCommand(cli)
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+}
diff --git a/cli/command/network/remove.go b/cli/command/network/remove.go
index cefd06c065..b584a4c37c 100644
--- a/cli/command/network/remove.go
+++ b/cli/command/network/remove.go
@@ -46,10 +46,15 @@ func runRemove(ctx context.Context, dockerCli command.Cli, networks []string, op
 	status := 0
 
 	for _, name := range networks {
-		if nw, _, err := client.NetworkInspectWithRaw(ctx, name, types.NetworkInspectOptions{}); err == nil &&
-			nw.Ingress &&
-			!command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), ingressWarning) {
-			continue
+		nw, _, err := client.NetworkInspectWithRaw(ctx, name, types.NetworkInspectOptions{})
+		if err == nil && nw.Ingress {
+			r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), ingressWarning)
+			if err != nil {
+				return err
+			}
+			if !r {
+				continue
+			}
 		}
 		if err := client.NetworkRemove(ctx, name); err != nil {
 			if opts.force && errdefs.IsNotFound(err) {
diff --git a/cli/command/network/remove_test.go b/cli/command/network/remove_test.go
index 98ea2592f6..5ad2a61df9 100644
--- a/cli/command/network/remove_test.go
+++ b/cli/command/network/remove_test.go
@@ -5,7 +5,9 @@ import (
 	"io"
 	"testing"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/docker/cli/internal/test"
+	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/errdefs"
 	"github.com/pkg/errors"
 	"gotest.tools/v3/assert"
@@ -94,3 +96,27 @@ func TestNetworkRemoveForce(t *testing.T) {
 		})
 	}
 }
+
+func TestNetworkRemovePromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		networkRemoveFunc: func(ctx context.Context, networkID string) error {
+			return errors.New("fakeClient networkRemoveFunc should not be called")
+		},
+		networkInspectFunc: func(ctx context.Context, networkID string, options types.NetworkInspectOptions) (types.NetworkResource, []byte, error) {
+			return types.NetworkResource{
+				ID:      "existing-network",
+				Name:    "existing-network",
+				Ingress: true,
+			}, nil, nil
+		},
+	})
+	cmd := newRemoveCommand(cli)
+	cmd.SetArgs([]string{"existing-network"})
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+}
diff --git a/cli/command/plugin/client_test.go b/cli/command/plugin/client_test.go
index c2bd136d0c..8eaf06896d 100644
--- a/cli/command/plugin/client_test.go
+++ b/cli/command/plugin/client_test.go
@@ -19,6 +19,7 @@ type fakeClient struct {
 	pluginInstallFunc func(name string, options types.PluginInstallOptions) (io.ReadCloser, error)
 	pluginListFunc    func(filter filters.Args) (types.PluginsListResponse, error)
 	pluginInspectFunc func(name string) (*types.Plugin, []byte, error)
+	pluginUpgradeFunc func(name string, options types.PluginInstallOptions) (io.ReadCloser, error)
 }
 
 func (c *fakeClient) PluginCreate(_ context.Context, createContext io.Reader, createOptions types.PluginCreateOptions) error {
@@ -75,3 +76,10 @@ func (c *fakeClient) PluginInspectWithRaw(_ context.Context, name string) (*type
 func (c *fakeClient) Info(context.Context) (system.Info, error) {
 	return system.Info{}, nil
 }
+
+func (c *fakeClient) PluginUpgrade(ctx context.Context, name string, options types.PluginInstallOptions) (io.ReadCloser, error) {
+	if c.pluginUpgradeFunc != nil {
+		return c.pluginUpgradeFunc(name, options)
+	}
+	return nil, nil
+}
diff --git a/cli/command/plugin/install.go b/cli/command/plugin/install.go
index beea9af86d..f1aa9d8725 100644
--- a/cli/command/plugin/install.go
+++ b/cli/command/plugin/install.go
@@ -142,6 +142,7 @@ func acceptPrivileges(dockerCli command.Cli, name string) func(privileges types.
 		for _, privilege := range privileges {
 			fmt.Fprintf(dockerCli.Out(), " - %s: %v\n", privilege.Name, privilege.Value)
 		}
-		return command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), "Do you grant the above permissions?"), nil
+		ctx := context.TODO()
+		return command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), "Do you grant the above permissions?")
 	}
 }
diff --git a/cli/command/plugin/testdata/plugin-upgrade-terminate.golden b/cli/command/plugin/testdata/plugin-upgrade-terminate.golden
new file mode 100644
index 0000000000..511aad36cc
--- /dev/null
+++ b/cli/command/plugin/testdata/plugin-upgrade-terminate.golden
@@ -0,0 +1,2 @@
+Upgrading plugin foo/bar from localhost:5000/foo/bar:v0.1.0 to localhost:5000/foo/bar:v1.0.0
+Plugin images do not match, are you sure? [y/N] 
\ No newline at end of file
diff --git a/cli/command/plugin/upgrade.go b/cli/command/plugin/upgrade.go
index 5134f3642d..fc7abb4127 100644
--- a/cli/command/plugin/upgrade.go
+++ b/cli/command/plugin/upgrade.go
@@ -63,7 +63,10 @@ func runUpgrade(ctx context.Context, dockerCli command.Cli, opts pluginOptions)
 
 	fmt.Fprintf(dockerCli.Out(), "Upgrading plugin %s from %s to %s\n", p.Name, reference.FamiliarString(old), reference.FamiliarString(remote))
 	if !opts.skipRemoteCheck && remote.String() != old.String() {
-		if !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), "Plugin images do not match, are you sure?") {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), "Plugin images do not match, are you sure?"); !r || err != nil {
+			if err != nil {
+				return errors.Wrap(err, "canceling upgrade request")
+			}
 			return errors.New("canceling upgrade request")
 		}
 	}
diff --git a/cli/command/plugin/upgrade_test.go b/cli/command/plugin/upgrade_test.go
new file mode 100644
index 0000000000..6511e4364c
--- /dev/null
+++ b/cli/command/plugin/upgrade_test.go
@@ -0,0 +1,42 @@
+package plugin
+
+import (
+	"context"
+	"io"
+	"testing"
+
+	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/internal/test"
+	"github.com/docker/docker/api/types"
+	"github.com/pkg/errors"
+	"gotest.tools/v3/assert"
+	"gotest.tools/v3/golden"
+)
+
+func TestUpgradePromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		pluginUpgradeFunc: func(name string, options types.PluginInstallOptions) (io.ReadCloser, error) {
+			return nil, errors.New("should not be called")
+		},
+		pluginInspectFunc: func(name string) (*types.Plugin, []byte, error) {
+			return &types.Plugin{
+				ID:              "5724e2c8652da337ab2eedd19fc6fc0ec908e4bd907c7421bf6a8dfc70c4c078",
+				Name:            "foo/bar",
+				Enabled:         false,
+				PluginReference: "localhost:5000/foo/bar:v0.1.0",
+			}, []byte{}, nil
+		},
+	})
+	cmd := newUpgradeCommand(cli)
+	// need to set a remote address that does not match the plugin
+	// reference sent by the `pluginInspectFunc`
+	cmd.SetArgs([]string{"foo/bar", "localhost:5000/foo/bar:v1.0.0"})
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+	golden.Assert(t, cli.OutBuffer().String(), "plugin-upgrade-terminate.golden")
+}
diff --git a/cli/command/system/client_test.go b/cli/command/system/client_test.go
index a275426fe1..01dc4b3d25 100644
--- a/cli/command/system/client_test.go
+++ b/cli/command/system/client_test.go
@@ -5,15 +5,18 @@ import (
 
 	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/api/types/events"
+	"github.com/docker/docker/api/types/filters"
 	"github.com/docker/docker/client"
 )
 
 type fakeClient struct {
 	client.Client
 
-	version       string
-	serverVersion func(ctx context.Context) (types.Version, error)
-	eventsFn      func(context.Context, types.EventsOptions) (<-chan events.Message, <-chan error)
+	version            string
+	serverVersion      func(ctx context.Context) (types.Version, error)
+	eventsFn           func(context.Context, types.EventsOptions) (<-chan events.Message, <-chan error)
+	containerPruneFunc func(ctx context.Context, pruneFilters filters.Args) (types.ContainersPruneReport, error)
+	networkPruneFunc   func(ctx context.Context, pruneFilter filters.Args) (types.NetworksPruneReport, error)
 }
 
 func (cli *fakeClient) ServerVersion(ctx context.Context) (types.Version, error) {
@@ -27,3 +30,17 @@ func (cli *fakeClient) ClientVersion() string {
 func (cli *fakeClient) Events(ctx context.Context, opts types.EventsOptions) (<-chan events.Message, <-chan error) {
 	return cli.eventsFn(ctx, opts)
 }
+
+func (cli *fakeClient) ContainersPrune(ctx context.Context, pruneFilters filters.Args) (types.ContainersPruneReport, error) {
+	if cli.containerPruneFunc != nil {
+		return cli.containerPruneFunc(ctx, pruneFilters)
+	}
+	return types.ContainersPruneReport{}, nil
+}
+
+func (cli *fakeClient) NetworksPrune(ctx context.Context, pruneFilter filters.Args) (types.NetworksPruneReport, error) {
+	if cli.networkPruneFunc != nil {
+		return cli.networkPruneFunc(ctx, pruneFilter)
+	}
+	return types.NetworksPruneReport{}, nil
+}
diff --git a/cli/command/system/prune.go b/cli/command/system/prune.go
index d91c450bf6..b3200ecfad 100644
--- a/cli/command/system/prune.go
+++ b/cli/command/system/prune.go
@@ -74,8 +74,10 @@ func runPrune(ctx context.Context, dockerCli command.Cli, options pruneOptions)
 	if options.pruneVolumes && options.filter.Value().Contains("until") {
 		return fmt.Errorf(`ERROR: The "until" filter is not supported with "--volumes"`)
 	}
-	if !options.force && !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), confirmationMessage(dockerCli, options)) {
-		return nil
+	if !options.force {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), confirmationMessage(dockerCli, options)); !r || err != nil {
+			return err
+		}
 	}
 	pruneFuncs := []func(ctx context.Context, dockerCli command.Cli, all bool, filter opts.FilterOpt) (uint64, string, error){
 		container.RunPrune,
diff --git a/cli/command/system/prune_test.go b/cli/command/system/prune_test.go
index ff0f7ae699..30cfb727a2 100644
--- a/cli/command/system/prune_test.go
+++ b/cli/command/system/prune_test.go
@@ -1,10 +1,15 @@
 package system
 
 import (
+	"context"
 	"testing"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/docker/cli/cli/config/configfile"
 	"github.com/docker/cli/internal/test"
+	"github.com/docker/docker/api/types"
+	"github.com/docker/docker/api/types/filters"
+	"github.com/pkg/errors"
 	"gotest.tools/v3/assert"
 	is "gotest.tools/v3/assert/cmp"
 )
@@ -49,3 +54,23 @@ func TestPrunePromptFilters(t *testing.T) {
 Are you sure you want to continue? [y/N] `
 	assert.Check(t, is.Equal(expected, cli.OutBuffer().String()))
 }
+
+func TestSystemPrunePromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		containerPruneFunc: func(ctx context.Context, pruneFilters filters.Args) (types.ContainersPruneReport, error) {
+			return types.ContainersPruneReport{}, errors.New("fakeClient containerPruneFunc should not be called")
+		},
+		networkPruneFunc: func(ctx context.Context, pruneFilters filters.Args) (types.NetworksPruneReport, error) {
+			return types.NetworksPruneReport{}, errors.New("fakeClient networkPruneFunc should not be called")
+		},
+	})
+
+	cmd := newPruneCommand(cli)
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+}
diff --git a/cli/command/trust/revoke.go b/cli/command/trust/revoke.go
index 0c52aaeebd..ac391a69c2 100644
--- a/cli/command/trust/revoke.go
+++ b/cli/command/trust/revoke.go
@@ -3,7 +3,6 @@ package trust
 import (
 	"context"
 	"fmt"
-	"os"
 
 	"github.com/docker/cli/cli"
 	"github.com/docker/cli/cli/command"
@@ -44,7 +43,11 @@ func revokeTrust(ctx context.Context, dockerCLI command.Cli, remote string, opti
 		return fmt.Errorf("cannot use a digest reference for IMAGE:TAG")
 	}
 	if imgRefAndAuth.Tag() == "" && !options.forceYes {
-		deleteRemote := command.PromptForConfirmation(os.Stdin, dockerCLI.Out(), fmt.Sprintf("Please confirm you would like to delete all signature data for %s?", remote))
+		deleteRemote, err := command.PromptForConfirmation(ctx, dockerCLI.In(), dockerCLI.Out(), fmt.Sprintf("Please confirm you would like to delete all signature data for %s?", remote))
+		if err != nil {
+			fmt.Fprintf(dockerCLI.Out(), "\nAborting action.\n")
+			return errors.Wrap(err, "aborting action")
+		}
 		if !deleteRemote {
 			fmt.Fprintf(dockerCLI.Out(), "\nAborting action.\n")
 			return nil
diff --git a/cli/command/trust/revoke_test.go b/cli/command/trust/revoke_test.go
index ca20189adb..a48e9898d5 100644
--- a/cli/command/trust/revoke_test.go
+++ b/cli/command/trust/revoke_test.go
@@ -1,9 +1,11 @@
 package trust
 
 import (
+	"context"
 	"io"
 	"testing"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/docker/cli/cli/trust"
 	"github.com/docker/cli/internal/test"
 	"github.com/docker/cli/internal/test/notary"
@@ -12,6 +14,7 @@ import (
 	"github.com/theupdateframework/notary/trustpinning"
 	"gotest.tools/v3/assert"
 	is "gotest.tools/v3/assert/cmp"
+	"gotest.tools/v3/golden"
 )
 
 func TestTrustRevokeCommandErrors(t *testing.T) {
@@ -148,3 +151,18 @@ func TestGetSignableRolesForTargetAndRemoveError(t *testing.T) {
 	err = getSignableRolesForTargetAndRemove(target, notaryRepo)
 	assert.Error(t, err, "client is offline")
 }
+
+func TestRevokeTrustPromptTermination(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{})
+	cmd := newRevokeCommand(cli)
+	cmd.SetArgs([]string{"example/trust-demo"})
+	test.TerminatePrompt(ctx, t, cmd, cli, func(t *testing.T, err error) {
+		t.Helper()
+		assert.ErrorIs(t, err, command.ErrPromptTerminated)
+	})
+	assert.Equal(t, cli.ErrBuffer().String(), "")
+	golden.Assert(t, cli.OutBuffer().String(), "trust-revoke-prompt-termination.golden")
+}
diff --git a/cli/command/trust/signer_remove.go b/cli/command/trust/signer_remove.go
index bef3d3b271..06deaa7e0d 100644
--- a/cli/command/trust/signer_remove.go
+++ b/cli/command/trust/signer_remove.go
@@ -3,7 +3,6 @@ package trust
 import (
 	"context"
 	"fmt"
-	"os"
 	"strings"
 
 	"github.com/docker/cli/cli"
@@ -76,6 +75,22 @@ func isLastSignerForReleases(roleWithSig data.Role, allRoles []client.RoleWithSi
 	return counter < releasesRoleWithSigs.Threshold, nil
 }
 
+func maybePromptForSignerRemoval(ctx context.Context, dockerCLI command.Cli, repoName, signerName string, isLastSigner, forceYes bool) (bool, error) {
+	if isLastSigner && !forceYes {
+		message := fmt.Sprintf("The signer \"%s\" signed the last released version of %s. "+
+			"Removing this signer will make %s unpullable. "+
+			"Are you sure you want to continue?",
+			signerName, repoName, repoName,
+		)
+		removeSigner, err := command.PromptForConfirmation(ctx, dockerCLI.In(), dockerCLI.Out(), message)
+		if err != nil {
+			return false, err
+		}
+		return removeSigner, nil
+	}
+	return false, nil
+}
+
 // removeSingleSigner attempts to remove a single signer and returns whether signer removal happened.
 // The signer not being removed doesn't necessarily raise an error e.g. user choosing "No" when prompted for confirmation.
 func removeSingleSigner(ctx context.Context, dockerCLI command.Cli, repoName, signerName string, forceYes bool) (bool, error) {
@@ -110,28 +125,26 @@ func removeSingleSigner(ctx context.Context, dockerCLI command.Cli, repoName, si
 	if err != nil {
 		return false, err
 	}
-	if ok, err := isLastSignerForReleases(role, allRoles); ok && !forceYes {
-		removeSigner := command.PromptForConfirmation(os.Stdin, dockerCLI.Out(), fmt.Sprintf("The signer \"%s\" signed the last released version of %s. "+
-			"Removing this signer will make %s unpullable. "+
-			"Are you sure you want to continue?",
-			signerName, repoName, repoName,
-		))
 
-		if !removeSigner {
-			fmt.Fprintf(dockerCLI.Out(), "\nAborting action.\n")
-			return false, nil
-		}
-	} else if err != nil {
-		return false, err
-	}
-	if err = notaryRepo.RemoveDelegationKeys(releasesRoleTUFName, role.KeyIDs); err != nil {
-		return false, err
-	}
-	if err = notaryRepo.RemoveDelegationRole(signerDelegation); err != nil {
+	isLastSigner, err := isLastSignerForReleases(role, allRoles)
+	if err != nil {
 		return false, err
 	}
 
-	if err = notaryRepo.Publish(); err != nil {
+	ok, err := maybePromptForSignerRemoval(ctx, dockerCLI, repoName, signerName, isLastSigner, forceYes)
+	if err != nil || !ok {
+		fmt.Fprintf(dockerCLI.Out(), "\nAborting action.\n")
+		return false, err
+	}
+
+	if err := notaryRepo.RemoveDelegationKeys(releasesRoleTUFName, role.KeyIDs); err != nil {
+		return false, err
+	}
+	if err := notaryRepo.RemoveDelegationRole(signerDelegation); err != nil {
+		return false, err
+	}
+
+	if err := notaryRepo.Publish(); err != nil {
 		return false, err
 	}
 
diff --git a/cli/command/trust/signer_remove_test.go b/cli/command/trust/signer_remove_test.go
index 05fa679715..9b54bcaf2f 100644
--- a/cli/command/trust/signer_remove_test.go
+++ b/cli/command/trust/signer_remove_test.go
@@ -111,7 +111,8 @@ func TestIsLastSignerForReleases(t *testing.T) {
 	releaserole.Name = releasesRoleTUFName
 	releaserole.Threshold = 1
 	allrole := []client.RoleWithSignatures{releaserole}
-	lastsigner, _ := isLastSignerForReleases(role, allrole)
+	lastsigner, err := isLastSignerForReleases(role, allrole)
+	assert.Error(t, err, "all signed tags are currently revoked, use docker trust sign to fix")
 	assert.Check(t, is.Equal(false, lastsigner))
 
 	role.KeyIDs = []string{"deadbeef"}
@@ -120,13 +121,15 @@ func TestIsLastSignerForReleases(t *testing.T) {
 	releaserole.Signatures = []data.Signature{sig}
 	releaserole.Threshold = 1
 	allrole = []client.RoleWithSignatures{releaserole}
-	lastsigner, _ = isLastSignerForReleases(role, allrole)
+	lastsigner, err = isLastSignerForReleases(role, allrole)
+	assert.NilError(t, err)
 	assert.Check(t, is.Equal(true, lastsigner))
 
 	sig.KeyID = "8badf00d"
 	releaserole.Signatures = []data.Signature{sig}
 	releaserole.Threshold = 1
 	allrole = []client.RoleWithSignatures{releaserole}
-	lastsigner, _ = isLastSignerForReleases(role, allrole)
+	lastsigner, err = isLastSignerForReleases(role, allrole)
+	assert.NilError(t, err)
 	assert.Check(t, is.Equal(false, lastsigner))
 }
diff --git a/cli/command/trust/testdata/trust-revoke-prompt-termination.golden b/cli/command/trust/testdata/trust-revoke-prompt-termination.golden
new file mode 100644
index 0000000000..bf854da789
--- /dev/null
+++ b/cli/command/trust/testdata/trust-revoke-prompt-termination.golden
@@ -0,0 +1,2 @@
+Please confirm you would like to delete all signature data for example/trust-demo? [y/N] 
+Aborting action.
diff --git a/cli/command/utils.go b/cli/command/utils.go
index 5c83efc986..df1f876faf 100644
--- a/cli/command/utils.go
+++ b/cli/command/utils.go
@@ -5,12 +5,15 @@ package command
 
 import (
 	"bufio"
+	"context"
 	"fmt"
 	"io"
 	"os"
+	"os/signal"
 	"path/filepath"
 	"runtime"
 	"strings"
+	"syscall"
 
 	"github.com/docker/cli/cli/streams"
 	"github.com/docker/docker/api/types/filters"
@@ -72,12 +75,21 @@ func PrettyPrint(i any) string {
 	}
 }
 
-// PromptForConfirmation requests and checks confirmation from user.
-// This will display the provided message followed by ' [y/N] '. If
-// the user input 'y' or 'Y' it returns true other false.  If no
-// message is provided "Are you sure you want to proceed? [y/N] "
-// will be used instead.
-func PromptForConfirmation(ins io.Reader, outs io.Writer, message string) bool {
+type PromptError error
+
+var ErrPromptTerminated = PromptError(errors.New("prompt terminated"))
+
+// PromptForConfirmation requests and checks confirmation from the user.
+// This will display the provided message followed by ' [y/N] '. If the user
+// input 'y' or 'Y' it returns true otherwise false. If no message is provided,
+// "Are you sure you want to proceed? [y/N] " will be used instead.
+//
+// If the user terminates the CLI with SIGINT or SIGTERM while the prompt is
+// active, the prompt will return false with an ErrPromptTerminated error.
+// When the prompt returns an error, the caller should propagate the error up
+// the stack and close the io.Reader used for the prompt which will prevent the
+// background goroutine from blocking indefinitely.
+func PromptForConfirmation(ctx context.Context, ins io.Reader, outs io.Writer, message string) (bool, error) {
 	if message == "" {
 		message = "Are you sure you want to proceed?"
 	}
@@ -90,9 +102,31 @@ func PromptForConfirmation(ins io.Reader, outs io.Writer, message string) bool {
 		ins = streams.NewIn(os.Stdin)
 	}
 
-	reader := bufio.NewReader(ins)
-	answer, _, _ := reader.ReadLine()
-	return strings.ToLower(string(answer)) == "y"
+	result := make(chan bool)
+
+	// Catch the termination signal and exit the prompt gracefully.
+	// The caller is responsible for properly handling the termination.
+	notifyCtx, notifyCancel := signal.NotifyContext(ctx, syscall.SIGINT, syscall.SIGTERM)
+	defer notifyCancel()
+
+	go func() {
+		var res bool
+		scanner := bufio.NewScanner(ins)
+		if scanner.Scan() {
+			answer := strings.TrimSpace(scanner.Text())
+			if strings.EqualFold(answer, "y") {
+				res = true
+			}
+		}
+		result <- res
+	}()
+
+	select {
+	case <-notifyCtx.Done():
+		return false, ErrPromptTerminated
+	case r := <-result:
+		return r, nil
+	}
 }
 
 // PruneFilters returns consolidated prune filters obtained from config.json and cli
diff --git a/cli/command/utils_test.go b/cli/command/utils_test.go
index 5ca5d0b3bb..869b33b644 100644
--- a/cli/command/utils_test.go
+++ b/cli/command/utils_test.go
@@ -1,36 +1,46 @@
-package command
+package command_test
 
 import (
+	"bufio"
+	"bytes"
+	"context"
+	"fmt"
+	"io"
 	"os"
 	"path/filepath"
+	"strings"
+	"syscall"
 	"testing"
+	"time"
 
+	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/internal/test"
 	"github.com/pkg/errors"
 	"gotest.tools/v3/assert"
 )
 
 func TestStringSliceReplaceAt(t *testing.T) {
-	out, ok := StringSliceReplaceAt([]string{"abc", "foo", "bar", "bax"}, []string{"foo", "bar"}, []string{"baz"}, -1)
+	out, ok := command.StringSliceReplaceAt([]string{"abc", "foo", "bar", "bax"}, []string{"foo", "bar"}, []string{"baz"}, -1)
 	assert.Assert(t, ok)
 	assert.DeepEqual(t, []string{"abc", "baz", "bax"}, out)
 
-	out, ok = StringSliceReplaceAt([]string{"foo"}, []string{"foo", "bar"}, []string{"baz"}, -1)
+	out, ok = command.StringSliceReplaceAt([]string{"foo"}, []string{"foo", "bar"}, []string{"baz"}, -1)
 	assert.Assert(t, !ok)
 	assert.DeepEqual(t, []string{"foo"}, out)
 
-	out, ok = StringSliceReplaceAt([]string{"abc", "foo", "bar", "bax"}, []string{"foo", "bar"}, []string{"baz"}, 0)
+	out, ok = command.StringSliceReplaceAt([]string{"abc", "foo", "bar", "bax"}, []string{"foo", "bar"}, []string{"baz"}, 0)
 	assert.Assert(t, !ok)
 	assert.DeepEqual(t, []string{"abc", "foo", "bar", "bax"}, out)
 
-	out, ok = StringSliceReplaceAt([]string{"foo", "bar", "bax"}, []string{"foo", "bar"}, []string{"baz"}, 0)
+	out, ok = command.StringSliceReplaceAt([]string{"foo", "bar", "bax"}, []string{"foo", "bar"}, []string{"baz"}, 0)
 	assert.Assert(t, ok)
 	assert.DeepEqual(t, []string{"baz", "bax"}, out)
 
-	out, ok = StringSliceReplaceAt([]string{"abc", "foo", "bar", "baz"}, []string{"foo", "bar"}, nil, -1)
+	out, ok = command.StringSliceReplaceAt([]string{"abc", "foo", "bar", "baz"}, []string{"foo", "bar"}, nil, -1)
 	assert.Assert(t, ok)
 	assert.DeepEqual(t, []string{"abc", "baz"}, out)
 
-	out, ok = StringSliceReplaceAt([]string{"foo"}, nil, []string{"baz"}, -1)
+	out, ok = command.StringSliceReplaceAt([]string{"foo"}, nil, []string{"baz"}, -1)
 	assert.Assert(t, !ok)
 	assert.DeepEqual(t, []string{"foo"}, out)
 }
@@ -59,7 +69,7 @@ func TestValidateOutputPath(t *testing.T) {
 
 	for _, testcase := range testcases {
 		t.Run(testcase.path, func(t *testing.T) {
-			err := ValidateOutputPath(testcase.path)
+			err := command.ValidateOutputPath(testcase.path)
 			if testcase.err == nil {
 				assert.NilError(t, err)
 			} else {
@@ -68,3 +78,177 @@ func TestValidateOutputPath(t *testing.T) {
 		})
 	}
 }
+
+func TestPromptForConfirmation(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	type promptResult struct {
+		result bool
+		err    error
+	}
+
+	buf := new(bytes.Buffer)
+	bufioWriter := bufio.NewWriter(buf)
+
+	var (
+		promptWriter *io.PipeWriter
+		promptReader *io.PipeReader
+	)
+
+	defer func() {
+		if promptWriter != nil {
+			promptWriter.Close()
+		}
+		if promptReader != nil {
+			promptReader.Close()
+		}
+	}()
+
+	for _, tc := range []struct {
+		desc string
+		f    func(*testing.T, context.Context, chan promptResult)
+	}{
+		{"SIGINT", func(t *testing.T, ctx context.Context, c chan promptResult) {
+			t.Helper()
+
+			syscall.Kill(syscall.Getpid(), syscall.SIGINT)
+
+			select {
+			case <-ctx.Done():
+				t.Fatal("PromptForConfirmation did not return after SIGINT")
+			case r := <-c:
+				assert.Check(t, !r.result)
+				assert.ErrorContains(t, r.err, "prompt terminated")
+			}
+		}},
+		{"no", func(t *testing.T, ctx context.Context, c chan promptResult) {
+			t.Helper()
+
+			_, err := fmt.Fprint(promptWriter, "n\n")
+			assert.NilError(t, err)
+
+			select {
+			case <-ctx.Done():
+				t.Fatal("PromptForConfirmation did not return after user input `n`")
+			case r := <-c:
+				assert.Check(t, !r.result)
+				assert.NilError(t, r.err)
+			}
+		}},
+		{"yes", func(t *testing.T, ctx context.Context, c chan promptResult) {
+			t.Helper()
+
+			_, err := fmt.Fprint(promptWriter, "y\n")
+			assert.NilError(t, err)
+
+			select {
+			case <-ctx.Done():
+				t.Fatal("PromptForConfirmation did not return after user input `y`")
+			case r := <-c:
+				assert.Check(t, r.result)
+				assert.NilError(t, r.err)
+			}
+		}},
+		{"any", func(t *testing.T, ctx context.Context, c chan promptResult) {
+			t.Helper()
+
+			_, err := fmt.Fprint(promptWriter, "a\n")
+			assert.NilError(t, err)
+
+			select {
+			case <-ctx.Done():
+				t.Fatal("PromptForConfirmation did not return after user input `a`")
+			case r := <-c:
+				assert.Check(t, !r.result)
+				assert.NilError(t, r.err)
+			}
+		}},
+		{"with space", func(t *testing.T, ctx context.Context, c chan promptResult) {
+			t.Helper()
+
+			_, err := fmt.Fprint(promptWriter, " y\n")
+			assert.NilError(t, err)
+
+			select {
+			case <-ctx.Done():
+				t.Fatal("PromptForConfirmation did not return after user input ` y`")
+			case r := <-c:
+				assert.Check(t, r.result)
+				assert.NilError(t, r.err)
+			}
+		}},
+		{"reader closed", func(t *testing.T, ctx context.Context, c chan promptResult) {
+			t.Helper()
+
+			assert.NilError(t, promptReader.Close())
+
+			select {
+			case <-ctx.Done():
+				t.Fatal("PromptForConfirmation did not return after promptReader was closed")
+			case r := <-c:
+				assert.Check(t, !r.result)
+				assert.NilError(t, r.err)
+			}
+		}},
+	} {
+		t.Run("case="+tc.desc, func(t *testing.T) {
+			buf.Reset()
+			promptReader, promptWriter = io.Pipe()
+
+			wroteHook := make(chan struct{}, 1)
+			defer close(wroteHook)
+			promptOut := test.NewWriterWithHook(bufioWriter, func(p []byte) {
+				wroteHook <- struct{}{}
+			})
+
+			result := make(chan promptResult, 1)
+			defer close(result)
+			go func() {
+				r, err := command.PromptForConfirmation(ctx, promptReader, promptOut, "")
+				result <- promptResult{r, err}
+			}()
+
+			// wait for the Prompt to write to the buffer
+			pollForPromptOutput(ctx, t, wroteHook)
+			drainChannel(ctx, wroteHook)
+
+			assert.NilError(t, bufioWriter.Flush())
+			assert.Equal(t, strings.TrimSpace(buf.String()), "Are you sure you want to proceed? [y/N]")
+
+			resultCtx, resultCancel := context.WithTimeout(ctx, 100*time.Millisecond)
+			defer resultCancel()
+
+			tc.f(t, resultCtx, result)
+		})
+	}
+}
+
+func drainChannel(ctx context.Context, ch <-chan struct{}) {
+	go func() {
+		for {
+			select {
+			case <-ctx.Done():
+				return
+			case <-ch:
+			}
+		}
+	}()
+}
+
+func pollForPromptOutput(ctx context.Context, t *testing.T, wroteHook <-chan struct{}) {
+	t.Helper()
+
+	ctx, cancel := context.WithTimeout(ctx, 100*time.Millisecond)
+	defer cancel()
+
+	for {
+		select {
+		case <-ctx.Done():
+			t.Fatal("Prompt output was not written to before ctx was cancelled")
+			return
+		case <-wroteHook:
+			return
+		}
+	}
+}
diff --git a/cli/command/volume/prune.go b/cli/command/volume/prune.go
index 0756f8fbb7..eff271665b 100644
--- a/cli/command/volume/prune.go
+++ b/cli/command/volume/prune.go
@@ -80,8 +80,10 @@ func runPrune(ctx context.Context, dockerCli command.Cli, options pruneOptions)
 		// API < v1.42 removes all volumes (anonymous and named) by default.
 		warning = allVolumesWarning
 	}
-	if !options.force && !command.PromptForConfirmation(dockerCli.In(), dockerCli.Out(), warning) {
-		return 0, "", errdefs.Cancelled(errors.New("user cancelled operation"))
+	if !options.force {
+		if r, err := command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), warning); !r || err != nil {
+			return 0, "", errdefs.Cancelled(errors.New("user cancelled operation"))
+		}
 	}
 
 	report, err := dockerCli.Client().VolumesPrune(ctx, pruneFilters)
diff --git a/cli/command/volume/prune_test.go b/cli/command/volume/prune_test.go
index ec0b188894..03fbe9dcd0 100644
--- a/cli/command/volume/prune_test.go
+++ b/cli/command/volume/prune_test.go
@@ -1,6 +1,7 @@
 package volume
 
 import (
+	"context"
 	"fmt"
 	"io"
 	"runtime"
@@ -183,3 +184,19 @@ func simplePruneFunc(filters.Args) (types.VolumesPruneReport, error) {
 		SpaceReclaimed: 2000,
 	}, nil
 }
+
+func TestVolumePrunePromptTerminate(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	t.Cleanup(cancel)
+
+	cli := test.NewFakeCli(&fakeClient{
+		volumePruneFunc: func(filter filters.Args) (types.VolumesPruneReport, error) {
+			return types.VolumesPruneReport{}, errors.New("fakeClient volumePruneFunc should not be called")
+		},
+	})
+
+	cmd := NewPruneCommand(cli)
+	test.TerminatePrompt(ctx, t, cmd, cli, nil)
+
+	golden.Assert(t, cli.OutBuffer().String(), "volume-prune-terminate.golden")
+}
diff --git a/cli/command/volume/testdata/volume-prune-terminate.golden b/cli/command/volume/testdata/volume-prune-terminate.golden
new file mode 100644
index 0000000000..8e918f9c9e
--- /dev/null
+++ b/cli/command/volume/testdata/volume-prune-terminate.golden
@@ -0,0 +1,2 @@
+WARNING! This will remove anonymous local volumes not used by at least one container.
+Are you sure you want to continue? [y/N] 
diff --git a/internal/test/cmd.go b/internal/test/cmd.go
new file mode 100644
index 0000000000..562542e6f8
--- /dev/null
+++ b/internal/test/cmd.go
@@ -0,0 +1,83 @@
+package test
+
+import (
+	"context"
+	"os"
+	"syscall"
+	"testing"
+	"time"
+
+	"github.com/docker/cli/cli/streams"
+	"github.com/spf13/cobra"
+	"gotest.tools/v3/assert"
+)
+
+func TerminatePrompt(ctx context.Context, t *testing.T, cmd *cobra.Command, cli *FakeCli, assertFunc func(*testing.T, error)) {
+	t.Helper()
+
+	errChan := make(chan error)
+	defer close(errChan)
+
+	// wrap the out stream to detect when the prompt is ready
+	writerHookChan := make(chan struct{})
+	defer close(writerHookChan)
+
+	outStream := streams.NewOut(NewWriterWithHook(cli.OutBuffer(), func(p []byte) {
+		writerHookChan <- struct{}{}
+	}))
+	cli.SetOut(outStream)
+
+	r, _, err := os.Pipe()
+	assert.NilError(t, err)
+	cli.SetIn(streams.NewIn(r))
+
+	go func() {
+		errChan <- cmd.ExecuteContext(ctx)
+	}()
+
+	writeCtx, writeCancel := context.WithTimeout(ctx, 100*time.Millisecond)
+	defer writeCancel()
+
+	// wait for the prompt to be ready
+	select {
+	case <-writeCtx.Done():
+		t.Fatalf("command %s did not write prompt to stdout", cmd.Name())
+	case <-writerHookChan:
+		// drain the channel for future buffer writes
+		go func() {
+			for {
+				select {
+				case <-ctx.Done():
+					return
+				case <-writerHookChan:
+				}
+			}
+		}()
+	}
+
+	assert.Check(t, cli.OutBuffer().Len() > 0)
+
+	// a small delay to ensure the plugin is prompting
+	time.Sleep(100 * time.Microsecond)
+
+	errCtx, errCancel := context.WithTimeout(ctx, 100*time.Millisecond)
+	defer errCancel()
+
+	// sigint and sigterm are caught by the prompt
+	// this allows us to gracefully exit the prompt with a 0 exit code
+	syscall.Kill(syscall.Getpid(), syscall.SIGINT)
+
+	select {
+	case <-errCtx.Done():
+		t.Logf("command stdout:\n%s\n", cli.OutBuffer().String())
+		t.Logf("command stderr:\n%s\n", cli.ErrBuffer().String())
+		t.Fatalf("command %s did not return after SIGINT", cmd.Name())
+	case err := <-errChan:
+		if assertFunc != nil {
+			assertFunc(t, err)
+		} else {
+			assert.NilError(t, err)
+			assert.Equal(t, cli.ErrBuffer().String(), "")
+		}
+	}
+}
diff --git a/internal/test/writer.go b/internal/test/writer.go
new file mode 100644
index 0000000000..c4ceede21e
--- /dev/null
+++ b/internal/test/writer.go
@@ -0,0 +1,30 @@
+package test
+
+import (
+	"io"
+)
+
+// WriterWithHook is an io.Writer that calls a hook function
+// after every write.
+// This is useful in testing to wait for a write to complete,
+// or to check what was written.
+// To create a WriterWithHook use the NewWriterWithHook function.
+type WriterWithHook struct {
+	actualWriter io.Writer
+	hook         func([]byte)
+}
+
+// Write writes p to the actual writer and then calls the hook function.
+func (w *WriterWithHook) Write(p []byte) (n int, err error) {
+	defer w.hook(p)
+	return w.actualWriter.Write(p)
+}
+
+var _ io.Writer = (*WriterWithHook)(nil)
+
+// NewWriterWithHook returns a new WriterWithHook that still writes to the actualWriter
+// but also calls the hook function after every write.
+// The hook function is useful for testing, or waiting for a write to complete.
+func NewWriterWithHook(actualWriter io.Writer, hook func([]byte)) *WriterWithHook {
+	return &WriterWithHook{actualWriter: actualWriter, hook: hook}
+}