diff --git a/executor_test.go b/executor_test.go
index d810e652f0..6e3ff3e1ec 100644
--- a/executor_test.go
+++ b/executor_test.go
@@ -1160,6 +1160,10 @@ func TestIf(t *testing.T) {
 
 		// For loop with if
 		{name: "if-in-for-loop", task: "if-in-for-loop", verbose: true},
+
+		// Task-level if with dynamic variable
+		{name: "task-if-dynamic-true", task: "task-if-dynamic-true"},
+		{name: "task-if-dynamic-false", task: "task-if-dynamic-false", verbose: true},
 	}
 
 	for _, test := range tests {
diff --git a/task.go b/task.go
index 0184793c91..54cda92762 100644
--- a/task.go
+++ b/task.go
@@ -148,6 +148,20 @@ func (e *Executor) RunTask(ctx context.Context, call *Call) error {
 		return nil
 	}
 
+	// Check required vars early (before template compilation) if we can't prompt.
+	// This gives a clear "missing required variables" error instead of a template error.
+	if !e.canPrompt() {
+		if err := e.areTaskRequiredVarsSet(t); err != nil {
+			return err
+		}
+	}
+
+	t, err = e.CompiledTask(call)
+	if err != nil {
+		return err
+	}
+
+	// Check if condition after CompiledTask so dynamic variables are resolved
 	if strings.TrimSpace(t.If) != "" {
 		if err := execext.RunCommand(ctx, &execext.RunCommandOptions{
 			Command: t.If,
@@ -159,7 +173,7 @@ func (e *Executor) RunTask(ctx context.Context, call *Call) error {
 		}
 	}
 
-	// Prompt for missing required vars (just-in-time for sequential task calls)
+	// Prompt for missing required vars after if check (avoid prompting if task won't run)
 	prompted, err := e.promptTaskVars(t, call)
 	if err != nil {
 		return err
@@ -176,11 +190,6 @@ func (e *Executor) RunTask(ctx context.Context, call *Call) error {
 		return err
 	}
 
-	t, err = e.CompiledTask(call)
-	if err != nil {
-		return err
-	}
-
 	if err := e.areTaskRequiredVarsAllowedValuesSet(t); err != nil {
 		return err
 	}
diff --git a/testdata/if/Taskfile.yml b/testdata/if/Taskfile.yml
index 316b732ff0..72b72ed982 100644
--- a/testdata/if/Taskfile.yml
+++ b/testdata/if/Taskfile.yml
@@ -158,3 +158,21 @@ tasks:
     if: '{{ eq .ENV "dev" }}'
     cmds:
       - echo "should not appear"
+
+  # Task-level if with dynamic variable (condition met)
+  task-if-dynamic-true:
+    vars:
+      ENABLE_FEATURE:
+        sh: 'echo "true"'
+    if: '{{ eq .ENABLE_FEATURE "true" }}'
+    cmds:
+      - echo "dynamic feature enabled"
+
+  # Task-level if with dynamic variable (condition not met)
+  task-if-dynamic-false:
+    vars:
+      ENABLE_FEATURE:
+        sh: 'echo "false"'
+    if: '{{ eq .ENABLE_FEATURE "true" }}'
+    cmds:
+      - echo "should not appear"
diff --git a/testdata/if/testdata/TestIf-task-if-dynamic-false.golden b/testdata/if/testdata/TestIf-task-if-dynamic-false.golden
new file mode 100644
index 0000000000..f17ef42029
--- /dev/null
+++ b/testdata/if/testdata/TestIf-task-if-dynamic-false.golden
@@ -0,0 +1,2 @@
+task: dynamic variable: "echo \"false\"" result: "false"
+task: if condition not met - skipped: "task-if-dynamic-false"
diff --git a/testdata/if/testdata/TestIf-task-if-dynamic-true.golden b/testdata/if/testdata/TestIf-task-if-dynamic-true.golden
new file mode 100644
index 0000000000..4d1ec95b6a
--- /dev/null
+++ b/testdata/if/testdata/TestIf-task-if-dynamic-true.golden
@@ -0,0 +1 @@
+dynamic feature enabled