diff --git a/changes/11570-bp-url b/changes/11570-bp-url
new file mode 100644
index 0000000000..a88eeb484d
--- /dev/null
+++ b/changes/11570-bp-url
@@ -0,0 +1 @@
+* MDM: try to infer the bootstrap package name from the URL on upload if a content-disposition header is not provided.
diff --git a/pkg/file/validation.go b/pkg/file/validation.go
new file mode 100644
index 0000000000..b9152cae60
--- /dev/null
+++ b/pkg/file/validation.go
@@ -0,0 +1,13 @@
+package file
+
+import "strings"
+
+var InvalidMacOSChars = []rune{':', '\\', '*', '?', '"', '<', '>', '|', 0}
+
+func IsValidMacOSName(fileName string) bool {
+	if fileName == "" {
+		return false
+	}
+
+	return !strings.ContainsAny(fileName, string(InvalidMacOSChars))
+}
diff --git a/pkg/file/validation_test.go b/pkg/file/validation_test.go
new file mode 100644
index 0000000000..91d992f75b
--- /dev/null
+++ b/pkg/file/validation_test.go
@@ -0,0 +1,38 @@
+package file
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestIsValidMacOSName(t *testing.T) {
+	testCases := []struct {
+		name   string
+		input  string
+		output bool
+	}{
+		{"valid", "filename.txt", true},
+		{"spaces", "file name with spaces.txt", true},
+		{"dashes", "file-name-with-dashes.txt", true},
+		{"underscores", "file_underscored.txt", true},
+		{"non-ASCII characters", "中文文件名.txt", true},
+
+		{"colon", "file:name.txt", false},
+		{"backslash", "file\\name.txt", false},
+		{"asterisk", "file*name.txt", false},
+		{"question mark", "file?name.txt", false},
+		{"double quote", "file\"name.txt", false},
+		{"less than", "file<name.txt", false},
+		{"greater than", "file>name.txt", false},
+		{"pipe", "file|name.txt", false},
+		{"null character", "file\x00name.txt", false},
+		{"empty", "", false},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			require.Equal(t, tc.output, IsValidMacOSName(tc.input))
+		})
+	}
+}
diff --git a/server/service/apple_mdm.go b/server/service/apple_mdm.go
index c4b9d3514b..077a407c5f 100644
--- a/server/service/apple_mdm.go
+++ b/server/service/apple_mdm.go
@@ -17,6 +17,7 @@ import (
 
 	"github.com/VividCortex/mysqlerr"
 	"github.com/docker/go-units"
+	"github.com/fleetdm/fleet/v4/pkg/file"
 	"github.com/fleetdm/fleet/v4/server/authz"
 	"github.com/fleetdm/fleet/v4/server/contexts/ctxerr"
 	"github.com/fleetdm/fleet/v4/server/contexts/license"
@@ -1662,6 +1663,12 @@ func (uploadBootstrapPackageRequest) DecodeRequest(ctx context.Context, r *http.
 	}
 
 	decoded.Package = r.MultipartForm.File["package"][0]
+	if !file.IsValidMacOSName(decoded.Package.Filename) {
+		return nil, &fleet.BadRequestError{
+			Message:     "package name contains invalid characters",
+			InternalErr: ctxerr.New(ctx, "package name contains invalid characters"),
+		}
+	}
 
 	// default is no team
 	decoded.TeamID = 0
diff --git a/server/service/client_mdm.go b/server/service/client_mdm.go
index 7918eb04bd..7a69c8939d 100644
--- a/server/service/client_mdm.go
+++ b/server/service/client_mdm.go
@@ -11,7 +11,9 @@ import (
 	"mime"
 	"mime/multipart"
 	"net/http"
+	"net/url"
 	"os"
+	"path"
 	"path/filepath"
 	"strings"
 
@@ -146,8 +148,32 @@ func (c *Client) ValidateBootstrapPackageFromURL(url string) (*fleet.MDMAppleBoo
 	return downloadRemoteMacosBootstrapPackage(url)
 }
 
-func downloadRemoteMacosBootstrapPackage(url string) (*fleet.MDMAppleBootstrapPackage, error) {
-	resp, err := http.Get(url) // nolint:gosec // we want this URL to be provided by the user. It will run on their machine.
+func extractFilenameFromPath(p string) string {
+	u, err := url.Parse(p)
+	if err != nil {
+		return ""
+	}
+
+	invalid := map[string]struct{}{
+		"":  {},
+		".": {},
+		"/": {},
+	}
+
+	b := path.Base(u.Path)
+	if _, ok := invalid[b]; ok {
+		return ""
+	}
+
+	if _, ok := invalid[path.Ext(b)]; ok {
+		return b + ".pkg"
+	}
+
+	return b
+}
+
+func downloadRemoteMacosBootstrapPackage(pkgURL string) (*fleet.MDMAppleBootstrapPackage, error) {
+	resp, err := http.Get(pkgURL) // nolint:gosec // we want this URL to be provided by the user. It will run on their machine.
 	if err != nil {
 		return nil, fmt.Errorf("downloading bootstrap package: %w", err)
 	}
@@ -166,6 +192,13 @@ func downloadRemoteMacosBootstrapPackage(url string) (*fleet.MDMAppleBootstrapPa
 			filename = params["filename"]
 		}
 	}
+
+	// if it fails, try to extract it from the URL
+	if filename == "" {
+		filename = extractFilenameFromPath(pkgURL)
+	}
+
+	// if all else fails, use a default name
 	if filename == "" {
 		filename = "bootstrap-package.pkg"
 	}
diff --git a/server/service/client_test.go b/server/service/client_test.go
index 136145b889..e5f55a64b5 100644
--- a/server/service/client_test.go
+++ b/server/service/client_test.go
@@ -202,3 +202,26 @@ spec:
 		})
 	}
 }
+
+func TestExtractFilenameFromPath(t *testing.T) {
+	cases := []struct {
+		in  string
+		out string
+	}{
+		{"http://example.com", ""},
+		{"http://example.com/", ""},
+		{"http://example.com?foo=bar", ""},
+		{"http://example.com/foo.pkg", "foo.pkg"},
+		{"http://example.com/foo.exe", "foo.exe"},
+		{"http://example.com/foo.pkg?bar=baz", "foo.pkg"},
+		{"http://example.com/foo.bar.pkg", "foo.bar.pkg"},
+		{"http://example.com/foo", "foo.pkg"},
+		{"http://example.com/foo/bar/baz", "baz.pkg"},
+		{"http://example.com/foo?bar=baz", "foo.pkg"},
+	}
+
+	for _, c := range cases {
+		got := extractFilenameFromPath(c.in)
+		require.Equalf(t, c.out, got, "for URL %s", c.in)
+	}
+}
diff --git a/server/service/integration_mdm_test.go b/server/service/integration_mdm_test.go
index 3112a70c37..c6c800f498 100644
--- a/server/service/integration_mdm_test.go
+++ b/server/service/integration_mdm_test.go
@@ -28,6 +28,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/fleetdm/fleet/v4/pkg/file"
 	"github.com/fleetdm/fleet/v4/server/config"
 	"github.com/fleetdm/fleet/v4/server/datastore/mysql"
 	"github.com/fleetdm/fleet/v4/server/datastore/redis/redistest"
@@ -2608,6 +2609,14 @@ func (s *integrationMDMTestSuite) TestBootstrapPackage() {
 	s.uploadBootstrapPackage(&fleet.MDMAppleBootstrapPackage{Bytes: signedPkg}, http.StatusBadRequest, "package multipart field is required")
 	// invalid
 	s.uploadBootstrapPackage(&fleet.MDMAppleBootstrapPackage{Bytes: invalidPkg, Name: "invalid.tar.gz"}, http.StatusBadRequest, "invalid file type")
+	// invalid names
+	for _, char := range file.InvalidMacOSChars {
+		s.uploadBootstrapPackage(
+			&fleet.MDMAppleBootstrapPackage{
+				Bytes: signedPkg,
+				Name:  fmt.Sprintf("invalid_%c_name.pkg", char),
+			}, http.StatusBadRequest, "")
+	}
 	// unsigned
 	s.uploadBootstrapPackage(&fleet.MDMAppleBootstrapPackage{Bytes: unsignedPkg, Name: "pkg.pkg"}, http.StatusBadRequest, "file is not signed")
 	// wrong TOC