diff --git a/cmd/earthly/app/run.go b/cmd/earthly/app/run.go
index 50047265d9..69b973a1e6 100644
--- a/cmd/earthly/app/run.go
+++ b/cmd/earthly/app/run.go
@@ -188,7 +188,6 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 			hintErr.Hint(),
 			hintErr.Message(),
 		)
-		app.BaseCLI.Console().HelpPrint(hintErr.Hint())
 
 		return 1
 	case errors.As(err, &autoSkipErr):
@@ -218,7 +217,6 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 
 		helpMsg = "Are you using --platform to target a different architecture? You may have to manually install QEMU.\n" +
 			"For more information see https://docs.earthbuild.dev/guides/multi-platform\n"
-		app.BaseCLI.Console().HelpPrint(helpMsg)
 		app.BaseCLI.Logbus().Run().SetGenericFatalError(
 			time.Now(),
 			logstream.FailureType_FAILURE_TYPE_OTHER,
@@ -236,7 +234,6 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 			args = stringutil.FilterElementsFromList(args, "--ci")
 			msg := "To debug your build, you can use the --interactive (-i) flag to drop into a shell of the failing RUN step"
 			helpMsg = fmt.Sprintf("%s: %q\n", msg, strings.Join(args, " "))
-			app.BaseCLI.Console().HelpPrint(helpMsg)
 		}
 		// This error would have been displayed earlier from the SolverMonitor.
 		// This SetGenericFatalError is a catch-all just in case that hasn't happened.
@@ -249,14 +246,49 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 
 		return 1
 	case strings.Contains(err.Error(), "security.insecure is not allowed"):
-		helpMsg := "earth --allow-privileged (earth -P) flag is required\n"
+		// Extract target info from error if available
+		targetInfo := ""
+
+		if ie != nil && isInterpreterError {
+			targetInfo = ie.TargetID
+		}
+
+		// If no target info from interpreter error, try to extract from args
+		if targetInfo == "" && len(args) > 1 {
+			for _, arg := range args[1:] {
+				if strings.HasPrefix(arg, "+") {
+					targetInfo = arg
+					break
+				}
+			}
+		}
+
+		userMsg := "This build requires privileged mode."
+
+		if targetInfo != "" {
+			userMsg = "Target " + targetInfo + " requires privileged mode."
+		}
+
+		// Create help message with actual target if available
+		flagExample := "earth -P +your-target"
+
+		if targetInfo != "" {
+			flagExample = "earth -P " + targetInfo
+		}
+
+		helpMsg := "To fix this, use one of the following:\n" +
+			"  • Run with the -P flag: " + flagExample + "\n" +
+			"  • Set environment variable: export EARTHLY_ALLOW_PRIVILEGED=true\n" +
+			"  • Add to config: earth config global.allow_privileged true"
+
 		app.BaseCLI.Logbus().Run().SetGenericFatalError(
 			time.Now(),
 			logstream.FailureType_FAILURE_TYPE_NEEDS_PRIVILEGED,
 			helpMsg,
-			err.Error(),
+			userMsg,
 		)
-		app.BaseCLI.Console().HelpPrint(helpMsg)
+
+		app.BaseCLI.Console().VerboseWarnf("Error: %s\n", err.Error())
 
 		return 9
 	case strings.Contains(err.Error(), errutil.EarthlyGitStdErrMagicString):
@@ -277,8 +309,6 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 			app.BaseCLI.Console().VerboseWarnf("Error: %v\n", err.Error())
 		}
 
-		app.BaseCLI.Console().HelpPrint(helpMsg)
-
 		return 1
 	case strings.Contains(err.Error(), "failed to compute cache key") && strings.Contains(err.Error(), ": not found"):
 		matches := notFoundRegex.FindStringSubmatch(err.Error())
@@ -310,7 +340,6 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 		helpMsg := fmt.Sprintf("%s responded with a rate limit error. This is usually because you are not logged in.\n"+
 			"You can login using the command:\n"+
 			"  docker login%s", registryName, registryHost)
-		app.BaseCLI.Console().HelpPrint(helpMsg)
 		app.BaseCLI.Logbus().Run().SetGenericFatalError(
 			time.Now(),
 			logstream.FailureType_FAILURE_TYPE_RATE_LIMITED,
@@ -338,7 +367,6 @@ func (app *EarthlyApp) handleError(ctx context.Context, err error, args []string
 			"Verify your account to lift this restriction."
 		app.BaseCLI.Logbus().Run().
 			SetGenericFatalError(time.Now(), logstream.FailureType_FAILURE_TYPE_OTHER, helpMsg, grpcErr.Message())
-		app.BaseCLI.Console().HelpPrint(helpMsg)
 
 		return 1
 	case grpcErrOK && grpcErr.Code() != codes.Canceled:
diff --git a/cmd/earthly/app/run_test.go b/cmd/earthly/app/run_test.go
index 96a5337b8f..b45a92b504 100644
--- a/cmd/earthly/app/run_test.go
+++ b/cmd/earthly/app/run_test.go
@@ -1,6 +1,7 @@
 package app
 
 import (
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/require"
@@ -43,3 +44,70 @@ func TestRedactSecretsFromArgs(t *testing.T) {
 		require.ElementsMatch(t, testCase.expected, actual)
 	}
 }
+
+func TestExtractTargetFromArgs(t *testing.T) {
+	t.Parallel()
+
+	for _, testCase := range []struct {
+		name     string
+		expected string
+		args     []string
+	}{
+		{
+			name:     "single target",
+			args:     []string{"earthly", "+target"},
+			expected: "+target",
+		},
+		{
+			name:     "target with flags before",
+			args:     []string{"earthly", "--verbose", "+build"},
+			expected: "+build",
+		},
+		{
+			name:     "target with flags after",
+			args:     []string{"earthly", "+test", "--ci"},
+			expected: "+test",
+		},
+		{
+			name:     "multiple targets - returns first",
+			args:     []string{"earthly", "+first", "+second"},
+			expected: "+first",
+		},
+		{
+			name:     "no target",
+			args:     []string{"earthly", "--version"},
+			expected: "",
+		},
+		{
+			name:     "empty args",
+			args:     []string{},
+			expected: "",
+		},
+		{
+			name:     "only command",
+			args:     []string{"earthly"},
+			expected: "",
+		},
+		{
+			name:     "target-like string but not target",
+			args:     []string{"earthly", "not-a-target", "+actual-target"},
+			expected: "+actual-target",
+		},
+	} {
+		t.Run(testCase.name, func(t *testing.T) {
+			t.Parallel()
+			// Simulate the target extraction logic from handleError
+			var targetInfo string
+			if len(testCase.args) > 1 {
+				for _, arg := range testCase.args[1:] {
+					if strings.HasPrefix(arg, "+") {
+						targetInfo = arg
+						break
+					}
+				}
+			}
+
+			require.Equal(t, testCase.expected, targetInfo)
+		})
+	}
+}
diff --git a/logbus/formatter/formatter.go b/logbus/formatter/formatter.go
index f8c2ca52ad..41f583a4a1 100644
--- a/logbus/formatter/formatter.go
+++ b/logbus/formatter/formatter.go
@@ -540,6 +540,10 @@ func (f *Formatter) printBuildFailure() {
 
 	c.Printf("%s%s\n", msgPrefix, failure.GetErrorMessage())
 
+	if failure.GetHelpMessage() != "" {
+		c.HelpPrint(failure.GetHelpMessage())
+	}
+
 	f.lastOutputWasOngoingUpdate = false
 	f.lastOutputWasProgress = false
 	f.lastCommandOutput = nil
diff --git a/tests/Earthfile b/tests/Earthfile
index 89b8190f89..22debd0db3 100644
--- a/tests/Earthfile
+++ b/tests/Earthfile
@@ -71,6 +71,7 @@ ga-no-qemu-group4:
     BUILD +push-arg-test
     BUILD +ci-arg-test
     BUILD +gen-dockerfile-test
+    BUILD +all-privileged-tests
     BUILD +chown-test
     BUILD +env-test
     BUILD +env-home-test
@@ -595,6 +596,68 @@ reject-privileged-import-test:
     DO +RUN_EARTHLY --earthfile=reject-privileged-import.earth --should_fail=true --extra_args="--allow-privileged" --target=+test-reject-copy
     DO +RUN_EARTHLY --earthfile=reject-privileged-import.earth --should_fail=true --extra_args="--allow-privileged" --target=+test-reject-cmd
 
+all-privileged-tests:
+    BUILD +privileged-run-test
+    BUILD +privileged-with-docker-test
+    BUILD +privileged-if-test
+    BUILD +privileged-for-test
+
+privileged-run-test:
+    # Test that RUN --privileged without -P flag shows improved error message
+    RUN echo "VERSION 0.8
+test:
+    FROM alpine:latest
+    RUN --privileged echo 'this requires privileged mode'
+" > Earthfile
+    DO +RUN_EARTHLY \
+        --should_fail=true \
+        --target=+test \
+        --output_contains="To fix this, use one of the following:"
+
+privileged-with-docker-test:
+    # Test that WITH DOCKER without -P flag shows improved error message
+    RUN echo "VERSION 0.8
+test:
+    FROM earthbuild/dind:alpine-3.22-docker-28.3.3-r4
+    WITH DOCKER
+        RUN docker ps
+    END
+" > Earthfile
+    DO +RUN_EARTHLY \
+        --should_fail=true \
+        --target=+test \
+        --output_contains="To fix this, use one of the following:"
+
+privileged-if-test:
+    # Test that IF --privileged without -P flag shows improved error message
+    RUN echo "VERSION 0.8
+test:
+    FROM alpine:latest
+    IF --privileged [ -f /proc/self/status ]
+        RUN echo 'found status'
+    END
+" > Earthfile
+    DO +RUN_EARTHLY \
+        --should_fail=true \
+        --target=+test \
+        --output_contains="To fix this, use one of the following:"
+
+privileged-for-test:
+    # Test that FOR --privileged without -P flag shows improved error message
+    RUN echo "VERSION 0.8
+test:
+    FROM alpine:latest
+    FOR --privileged file IN \$(ls)
+        RUN echo \$file
+    END
+" > Earthfile
+    DO +RUN_EARTHLY \
+        --should_fail=true \
+        --target=+test \
+        --output_contains="To fix this, use one of the following:"
+
+
+
 pass-args-test:
     COPY pass-args-sub-dir.earth subdir/Earthfile
     COPY pass-args-root.earth Earthfile
diff --git a/tests/with-docker/Earthfile b/tests/with-docker/Earthfile
index 31f96fa52c..1a85a48e5a 100644
--- a/tests/with-docker/Earthfile
+++ b/tests/with-docker/Earthfile
@@ -178,4 +178,4 @@ pre-script-test:
     COPY pre-script.sh /usr/share/earthly/dockerd-wrapper-pre-script
     WITH DOCKER
         RUN test -f /the-prescript-was-run
-    END
+    END
\ No newline at end of file