diff --git a/changelog/16441.txt b/changelog/16441.txt
new file mode 100644
index 0000000000000..f265483d86ea2
--- /dev/null
+++ b/changelog/16441.txt
@@ -0,0 +1,3 @@
+```release-note:improvement
+cli: CLI commands will print a warning if flags will be ignored because they are passed after positional arguments.
+```
diff --git a/command/base.go b/command/base.go
index 5f6a171dcee2c..bbad7beca2a2e 100644
--- a/command/base.go
+++ b/command/base.go
@@ -549,6 +549,7 @@ type FlagSets struct {
 	mainSet     *flag.FlagSet
 	hiddens     map[string]struct{}
 	completions complete.Flags
+	ui          cli.Ui
 }
 
 // NewFlagSets creates a new flag sets.
@@ -564,6 +565,7 @@ func NewFlagSets(ui cli.Ui) *FlagSets {
 		mainSet:     mainSet,
 		hiddens:     make(map[string]struct{}),
 		completions: complete.Flags{},
+		ui:          ui,
 	}
 }
 
@@ -582,8 +584,16 @@ func (f *FlagSets) Completions() complete.Flags {
 }
 
 // Parse parses the given flags, returning any errors.
+// Warnings, if any, regarding the arguments format are sent to stdout
 func (f *FlagSets) Parse(args []string) error {
-	return f.mainSet.Parse(args)
+	err := f.mainSet.Parse(args)
+
+	warnings := generateFlagWarnings(f.Args())
+	if warnings != "" {
+		f.ui.Warn(warnings)
+	}
+
+	return err
 }
 
 // Parsed reports whether the command-line flags have been parsed.
@@ -603,10 +613,10 @@ func (f *FlagSets) Visit(fn func(*flag.Flag)) {
 }
 
 // Help builds custom help for this command, grouping by flag set.
-func (fs *FlagSets) Help() string {
+func (f *FlagSets) Help() string {
 	var out bytes.Buffer
 
-	for _, set := range fs.flagSets {
+	for _, set := range f.flagSets {
 		printFlagTitle(&out, set.name+":")
 		set.VisitAll(func(f *flag.Flag) {
 			// Skip any hidden flags
diff --git a/command/base_helpers.go b/command/base_helpers.go
index f20cfebf71025..03e135a525a37 100644
--- a/command/base_helpers.go
+++ b/command/base_helpers.go
@@ -292,3 +292,19 @@ func parseFlagFile(raw string) (string, error) {
 
 	return raw, nil
 }
+
+func generateFlagWarnings(args []string) string {
+	var trailingFlags []string
+	for _, arg := range args {
+		if strings.HasPrefix(arg, "-") {
+			trailingFlags = append(trailingFlags, arg)
+		}
+	}
+
+	if len(trailingFlags) > 0 {
+		return fmt.Sprintf("Flags must be provided before positional arguments. "+
+			"The following arguments will not be parsed as flags: [%s]", strings.Join(trailingFlags, ","))
+	} else {
+		return ""
+	}
+}
diff --git a/command/base_helpers_test.go b/command/base_helpers_test.go
index df764d36e4db7..4703153df1b46 100644
--- a/command/base_helpers_test.go
+++ b/command/base_helpers_test.go
@@ -5,6 +5,7 @@ import (
 	"io"
 	"io/ioutil"
 	"os"
+	"strings"
 	"testing"
 	"time"
 )
@@ -209,3 +210,48 @@ func TestParseFlagFile(t *testing.T) {
 		})
 	}
 }
+
+func TestArgWarnings(t *testing.T) {
+	t.Parallel()
+
+	cases := []struct {
+		args     []string
+		expected string
+	}{
+		{
+			[]string{"a", "b", "c"},
+			"",
+		},
+		{
+			[]string{"a", "-b"},
+			"-b",
+		},
+		{
+			[]string{"a", "--b"},
+			"--b",
+		},
+		{
+			[]string{"a-b", "-c"},
+			"-c",
+		},
+		{
+			[]string{"a", "-b-c"},
+			"-b-c",
+		},
+		{
+			[]string{"-a", "b"},
+			"-a",
+		},
+	}
+
+	for _, tc := range cases {
+		tc := tc
+
+		t.Run(tc.expected, func(t *testing.T) {
+			warnings := generateFlagWarnings(tc.args)
+			if !strings.Contains(warnings, tc.expected) {
+				t.Fatalf("expected %s to contain %s", warnings, tc.expected)
+			}
+		})
+	}
+}