diff --git a/go.mod b/go.mod
index 2e653052c..a607e4adf 100644
--- a/go.mod
+++ b/go.mod
@@ -17,10 +17,10 @@ require (
 	github.com/cpuguy83/go-md2man/v2 v2.0.4
 	github.com/creack/pty v1.1.21
 	github.com/distribution/reference v0.5.0
-	github.com/gabriel-vasile/mimetype v1.4.4
+	github.com/gabriel-vasile/mimetype v1.4.5
 	github.com/gdamore/tcell/v2 v2.5.4
 	github.com/google/go-cmp v0.6.0
-	github.com/google/go-containerregistry v0.20.0
+	github.com/google/go-containerregistry v0.20.1
 	github.com/google/shlex v0.0.0-20191202100458-e7afc7fbc510
 	github.com/gorilla/websocket v1.5.3
 	github.com/hashicorp/go-multierror v1.1.1
@@ -158,7 +158,7 @@ require (
 	go.uber.org/zap v1.27.0 // indirect
 	golang.org/x/exp v0.0.0-20240112132812-db7319d0e0e3 // indirect
 	golang.org/x/mod v0.19.0 // indirect
-	golang.org/x/net v0.26.0 // indirect
+	golang.org/x/net v0.27.0 // indirect
 	golang.org/x/sys v0.22.0 // indirect
 	google.golang.org/genproto/googleapis/api v0.0.0-20240520151616-dc85e6b867a5 // indirect
 	google.golang.org/genproto/googleapis/rpc v0.0.0-20240520151616-dc85e6b867a5 // indirect
diff --git a/go.sum b/go.sum
index 460a2f65a..ffb608ffb 100644
--- a/go.sum
+++ b/go.sum
@@ -148,8 +148,8 @@ github.com/frankban/quicktest v1.14.6 h1:7Xjx+VpznH+oBnejlPUj8oUpdxnVs4f8XU8WnHk
 github.com/frankban/quicktest v1.14.6/go.mod h1:4ptaffx2x8+WTWXmUCuVU6aPUX1/Mz7zb5vbUoiM6w0=
 github.com/fsnotify/fsnotify v1.7.0 h1:8JEhPFa5W2WU7YfeZzPNqzMP6Lwt7L2715Ggo0nosvA=
 github.com/fsnotify/fsnotify v1.7.0/go.mod h1:40Bi/Hjc2AVfZrqy+aj+yEI+/bRxZnMJyTJwOpGvigM=
-github.com/gabriel-vasile/mimetype v1.4.4 h1:QjV6pZ7/XZ7ryI2KuyeEDE8wnh7fHP9YnQy+R0LnH8I=
-github.com/gabriel-vasile/mimetype v1.4.4/go.mod h1:JwLei5XPtWdGiMFB5Pjle1oEeoSeEuJfJE+TtfvdB/s=
+github.com/gabriel-vasile/mimetype v1.4.5 h1:J7wGKdGu33ocBOhGy0z653k/lFKLFDPJMG8Gql0kxn4=
+github.com/gabriel-vasile/mimetype v1.4.5/go.mod h1:ibHel+/kbxn9x2407k1izTA1S81ku1z/DlgOW2QE0M4=
 github.com/gdamore/encoding v1.0.0 h1:+7OoQ1Bc6eTm5niUzBa0Ctsh6JbMW6Ra+YNuAtDBdko=
 github.com/gdamore/encoding v1.0.0/go.mod h1:alR0ol34c49FCSBLjhosxzcPHQbf2trDkoo5dl+VrEg=
 github.com/gdamore/tcell/v2 v2.5.4 h1:TGU4tSjD3sCL788vFNeJnTdzpNKIw1H5dgLnJRQVv/k=
@@ -201,8 +201,8 @@ github.com/google/certificate-transparency-go v1.2.1 h1:4iW/NwzqOqYEEoCBEFP+jPbB
 github.com/google/certificate-transparency-go v1.2.1/go.mod h1:bvn/ytAccv+I6+DGkqpvSsEdiVGramgaSC6RD3tEmeE=
 github.com/google/go-cmp v0.6.0 h1:ofyhxvXcZhMsU5ulbFiLKl/XBFqE1GSq7atu8tAmTRI=
 github.com/google/go-cmp v0.6.0/go.mod h1:17dUlkBOakJ0+DkrSSNjCkIjxS6bF9zb3elmeNGIjoY=
-github.com/google/go-containerregistry v0.20.0 h1:wRqHpOeVh3DnenOrPy9xDOLdnLatiGuuNRVelR2gSbg=
-github.com/google/go-containerregistry v0.20.0/go.mod h1:YCMFNQeeXeLF+dnhhWkqDItx/JSkH01j1Kis4PsjzFI=
+github.com/google/go-containerregistry v0.20.1 h1:eTgx9QNYugV4DN5mz4U8hiAGTi1ybXn0TPi4Smd8du0=
+github.com/google/go-containerregistry v0.20.1/go.mod h1:YCMFNQeeXeLF+dnhhWkqDItx/JSkH01j1Kis4PsjzFI=
 github.com/google/gofuzz v1.2.0 h1:xRy4A+RhZaiKjJ1bPfwQ8sedCA+YS2YcCHW6ec7JMi0=
 github.com/google/gofuzz v1.2.0/go.mod h1:dBl0BpW6vV/+mYPU4Po3pmUjxk6FQPldtuIdl/M65Eg=
 github.com/google/s2a-go v0.1.7 h1:60BLSyTrOV4/haCDW4zb1guZItoSq8foHCXrAnjBo/o=
@@ -495,8 +495,8 @@ golang.org/x/mod v0.19.0/go.mod h1:hTbmBsO62+eylJbnUtE2MGJUyE7QWk4xUqPFrRgJ+7c=
 golang.org/x/net v0.0.0-20190620200207-3b0461eec859/go.mod h1:z5CRVTTTmAJ677TzLLGU+0bjPO0LkuOLi4/5GtJWs/s=
 golang.org/x/net v0.0.0-20210226172049-e18ecbb05110/go.mod h1:m0MpNAwzfU5UDzcl9v0D8zg8gWTRqZa9RBIspLL5mdg=
 golang.org/x/net v0.0.0-20220722155237-a158d28d115b/go.mod h1:XRhObCWvk6IyKnWLug+ECip1KBveYUHfp+8e9klMJ9c=
-golang.org/x/net v0.26.0 h1:soB7SVo0PWrY4vPW/+ay0jKDNScG2X9wFeYlXIvJsOQ=
-golang.org/x/net v0.26.0/go.mod h1:5YKkiSynbBIh3p6iOc/vibscux0x38BZDkn8sCUPxHE=
+golang.org/x/net v0.27.0 h1:5K3Njcw06/l2y9vpGCSdcxWOYHOUk3dVNGDXN+FvAys=
+golang.org/x/net v0.27.0/go.mod h1:dDi0PyhWNoiUOrAS8uXv/vnScO4wnHQO4mj9fn/RytE=
 golang.org/x/oauth2 v0.21.0 h1:tsimM75w1tF/uws5rbeHzIWxEqElMehnc+iW793zsZs=
 golang.org/x/oauth2 v0.21.0/go.mod h1:XYTD2NtWslqkgxebSiOHnXEap4TF09sJSc7H1sXbhtI=
 golang.org/x/sync v0.0.0-20190423024810-112230192c58/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
diff --git a/pkg/cmd/issue/edit/edit.go b/pkg/cmd/issue/edit/edit.go
index 1b775f88b..11a69383d 100644
--- a/pkg/cmd/issue/edit/edit.go
+++ b/pkg/cmd/issue/edit/edit.go
@@ -46,6 +46,7 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 	}
 
 	var bodyFile string
+	var removeMilestone bool
 
 	cmd := &cobra.Command{
 		Use:   "edit {<numbers> | <urls>}",
@@ -62,6 +63,7 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 			$ gh issue edit 23 --add-assignee "@me" --remove-assignee monalisa,hubot
 			$ gh issue edit 23 --add-project "Roadmap" --remove-project v1,v2
 			$ gh issue edit 23 --milestone "Version 1"
+			$ gh issue edit 23 --remove-milestone
 			$ gh issue edit 23 --body-file body.txt
 			$ gh issue edit 23 34 --add-label "help wanted"
 		`),
@@ -95,6 +97,14 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 				}
 			}
 
+			if err := cmdutil.MutuallyExclusive(
+				"specify only one of `--milestone` or `--remove-milestone`",
+				flags.Changed("milestone"),
+				removeMilestone,
+			); err != nil {
+				return err
+			}
+
 			if flags.Changed("title") {
 				opts.Editable.Title.Edited = true
 			}
@@ -107,8 +117,13 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 			if flags.Changed("add-project") || flags.Changed("remove-project") {
 				opts.Editable.Projects.Edited = true
 			}
-			if flags.Changed("milestone") {
+			if flags.Changed("milestone") || removeMilestone {
 				opts.Editable.Milestone.Edited = true
+
+				// Note that when `--remove-milestone` is provided, the value of
+				// `opts.Editable.Milestone.Value` will automatically be empty,
+				// which results in milestone association removal. For reference,
+				// see the `Editable.MilestoneId` method.
 			}
 
 			if !opts.Editable.Dirty() {
@@ -141,6 +156,7 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 	cmd.Flags().StringSliceVar(&opts.Editable.Projects.Add, "add-project", nil, "Add the issue to projects by `name`")
 	cmd.Flags().StringSliceVar(&opts.Editable.Projects.Remove, "remove-project", nil, "Remove the issue from projects by `name`")
 	cmd.Flags().StringVarP(&opts.Editable.Milestone.Value, "milestone", "m", "", "Edit the milestone the issue belongs to by `name`")
+	cmd.Flags().BoolVar(&removeMilestone, "remove-milestone", false, "Remove the milestone association from the issue")
 
 	return cmd
 }
diff --git a/pkg/cmd/issue/edit/edit_test.go b/pkg/cmd/issue/edit/edit_test.go
index db0b09d2d..40fe6491c 100644
--- a/pkg/cmd/issue/edit/edit_test.go
+++ b/pkg/cmd/issue/edit/edit_test.go
@@ -104,6 +104,11 @@ func TestNewCmdEdit(t *testing.T) {
 			},
 			wantsErr: false,
 		},
+		{
+			name:     "both body and body-file flags",
+			input:    "23 --body foo --body-file bar",
+			wantsErr: true,
+		},
 		{
 			name:  "add-assignee flag",
 			input: "23 --add-assignee monalisa,hubot",
@@ -206,6 +211,25 @@ func TestNewCmdEdit(t *testing.T) {
 			},
 			wantsErr: false,
 		},
+		{
+			name:  "remove-milestone flag",
+			input: "23 --remove-milestone",
+			output: EditOptions{
+				SelectorArgs: []string{"23"},
+				Editable: prShared.Editable{
+					Milestone: prShared.EditableString{
+						Value:  "",
+						Edited: true,
+					},
+				},
+			},
+			wantsErr: false,
+		},
+		{
+			name:     "both milestone and remove-milestone flags",
+			input:    "23 --milestone foo --remove-milestone",
+			wantsErr: true,
+		},
 		{
 			name:  "add label to multiple issues",
 			input: "23 34 --add-label bug",
@@ -221,17 +245,8 @@ func TestNewCmdEdit(t *testing.T) {
 			wantsErr: false,
 		},
 		{
-			name:  "interactive multiple issues",
-			input: "23 34",
-			output: EditOptions{
-				SelectorArgs: []string{"23", "34"},
-				Editable: prShared.Editable{
-					Labels: prShared.EditableSlice{
-						Add:    []string{"bug"},
-						Edited: true,
-					},
-				},
-			},
+			name:     "interactive multiple issues",
+			input:    "23 34",
 			wantsErr: true,
 		},
 	}
diff --git a/pkg/cmd/pr/edit/edit.go b/pkg/cmd/pr/edit/edit.go
index 3f80aa80a..9dc190011 100644
--- a/pkg/cmd/pr/edit/edit.go
+++ b/pkg/cmd/pr/edit/edit.go
@@ -43,6 +43,7 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 	}
 
 	var bodyFile string
+	var removeMilestone bool
 
 	cmd := &cobra.Command{
 		Use:   "edit [<number> | <url> | <branch>]",
@@ -63,6 +64,7 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 			$ gh pr edit 23 --add-assignee "@me" --remove-assignee monalisa,hubot
 			$ gh pr edit 23 --add-project "Roadmap" --remove-project v1,v2
 			$ gh pr edit 23 --milestone "Version 1"
+			$ gh pr edit 23 --remove-milestone
 		`),
 		Args: cobra.MaximumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
@@ -95,6 +97,14 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 				}
 			}
 
+			if err := cmdutil.MutuallyExclusive(
+				"specify only one of `--milestone` or `--remove-milestone`",
+				flags.Changed("milestone"),
+				removeMilestone,
+			); err != nil {
+				return err
+			}
+
 			if flags.Changed("title") {
 				opts.Editable.Title.Edited = true
 			}
@@ -116,8 +126,13 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 			if flags.Changed("add-project") || flags.Changed("remove-project") {
 				opts.Editable.Projects.Edited = true
 			}
-			if flags.Changed("milestone") {
+			if flags.Changed("milestone") || removeMilestone {
 				opts.Editable.Milestone.Edited = true
+
+				// Note that when `--remove-milestone` is provided, the value of
+				// `opts.Editable.Milestone.Value` will automatically be empty,
+				// which results in milestone association removal. For reference,
+				// see the `Editable.MilestoneId` method.
 			}
 
 			if !opts.Editable.Dirty() {
@@ -149,6 +164,7 @@ func NewCmdEdit(f *cmdutil.Factory, runF func(*EditOptions) error) *cobra.Comman
 	cmd.Flags().StringSliceVar(&opts.Editable.Projects.Add, "add-project", nil, "Add the pull request to projects by `name`")
 	cmd.Flags().StringSliceVar(&opts.Editable.Projects.Remove, "remove-project", nil, "Remove the pull request from projects by `name`")
 	cmd.Flags().StringVarP(&opts.Editable.Milestone.Value, "milestone", "m", "", "Edit the milestone the pull request belongs to by `name`")
+	cmd.Flags().BoolVar(&removeMilestone, "remove-milestone", false, "Remove the milestone association from the pull request")
 
 	_ = cmdutil.RegisterBranchCompletionFlags(f.GitClient, cmd, "base")
 
diff --git a/pkg/cmd/pr/edit/edit_test.go b/pkg/cmd/pr/edit/edit_test.go
index 0986797ea..3c4882961 100644
--- a/pkg/cmd/pr/edit/edit_test.go
+++ b/pkg/cmd/pr/edit/edit_test.go
@@ -112,6 +112,11 @@ func TestNewCmdEdit(t *testing.T) {
 			},
 			wantsErr: false,
 		},
+		{
+			name:     "both body and body-file flags",
+			input:    "23 --body foo --body-file bar",
+			wantsErr: true,
+		},
 		{
 			name:  "base flag",
 			input: "23 --base base-branch-name",
@@ -256,6 +261,25 @@ func TestNewCmdEdit(t *testing.T) {
 			},
 			wantsErr: false,
 		},
+		{
+			name:  "remove-milestone flag",
+			input: "23 --remove-milestone",
+			output: EditOptions{
+				SelectorArg: "23",
+				Editable: shared.Editable{
+					Milestone: shared.EditableString{
+						Value:  "",
+						Edited: true,
+					},
+				},
+			},
+			wantsErr: false,
+		},
+		{
+			name:     "both milestone and remove-milestone flags",
+			input:    "23 --milestone foo --remove-milestone",
+			wantsErr: true,
+		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {