diff --git a/sway-error/src/error.rs b/sway-error/src/error.rs
index 0b957921be9..8e4147e01db 100644
--- a/sway-error/src/error.rs
+++ b/sway-error/src/error.rs
@@ -653,6 +653,8 @@ pub enum CompileError {
     ConfigTimeConstantNotALiteral { span: Span },
     #[error("ref mut parameter not allowed for main()")]
     RefMutableNotAllowedInMain { param_name: Ident },
+    #[error("returning raw_ptrs are not allowed for main()")]
+    PointerReturnNotAllowedInMain { span: Span },
 }
 
 impl std::convert::From<TypeError> for CompileError {
@@ -828,6 +830,7 @@ impl Spanned for CompileError {
             ConfigTimeConstantNotAConstDecl { span } => span.clone(),
             ConfigTimeConstantNotALiteral { span } => span.clone(),
             RefMutableNotAllowedInMain { param_name } => param_name.span(),
+            PointerReturnNotAllowedInMain { span } => span.clone(),
         }
     }
 }
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/Forc.lock b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/Forc.lock
new file mode 100644
index 00000000000..0638ba9e991
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/Forc.lock
@@ -0,0 +1,14 @@
+[[package]]
+name = 'core'
+source = 'path+from-root-51D3AF48CE04FAE0'
+dependencies = []
+
+[[package]]
+name = 'raw_ptr_ret'
+source = 'root'
+dependencies = ['std']
+
+[[package]]
+name = 'std'
+source = 'path+from-root-51D3AF48CE04FAE0'
+dependencies = ['core']
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/Forc.toml b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/Forc.toml
new file mode 100644
index 00000000000..8d7e5d05906
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/Forc.toml
@@ -0,0 +1,8 @@
+[project]
+authors = ["Fuel Labs <contact@fuel.sh>"]
+entry = "main.sw"
+license = "Apache-2.0"
+name = "raw_ptr_ret"
+
+[dependencies]
+std = { path = "../../../../../../../sway-lib-std" }
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/src/main.sw b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/src/main.sw
new file mode 100644
index 00000000000..d8a58c7de7d
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/src/main.sw
@@ -0,0 +1,6 @@
+script;
+
+fn main() -> raw_ptr {
+    let ptr = asm(r1) { r1: raw_ptr };
+    ptr
+}
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/test.toml b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/test.toml
new file mode 100644
index 00000000000..9b9236281e8
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/raw_ptr_ret/test.toml
@@ -0,0 +1,4 @@
+category = "fail"
+
+# check: fn main() -> raw_ptr {
+# nextln: $()returning raw_ptrs are not allowed for main()
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/Forc.lock b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/Forc.lock
new file mode 100644
index 00000000000..fb42f43caf3
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/Forc.lock
@@ -0,0 +1,14 @@
+[[package]]
+name = 'core'
+source = 'path+from-root-D3556C503E51030C'
+dependencies = []
+
+[[package]]
+name = 'std'
+source = 'path+from-root-D3556C503E51030C'
+dependencies = ['core']
+
+[[package]]
+name = 'vec_ret'
+source = 'root'
+dependencies = ['std']
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/Forc.toml b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/Forc.toml
new file mode 100644
index 00000000000..b9613943adf
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/Forc.toml
@@ -0,0 +1,8 @@
+[project]
+authors = ["Fuel Labs <contact@fuel.sh>"]
+entry = "main.sw"
+license = "Apache-2.0"
+name = "vec_ret"
+
+[dependencies]
+std = { path = "../../../../../../../sway-lib-std" }
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/src/main.sw b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/src/main.sw
new file mode 100644
index 00000000000..ed0aa9652e2
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/src/main.sw
@@ -0,0 +1,8 @@
+script;
+
+use std::vec::Vec;
+
+fn main() -> Vec<u64> {
+    let vec = ~Vec::new();
+    vec
+}
diff --git a/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/test.toml b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/test.toml
new file mode 100644
index 00000000000..5fde6486495
--- /dev/null
+++ b/test/src/e2e_vm_tests/test_programs/should_fail/raw_ptr/vec_ret/test.toml
@@ -0,0 +1,4 @@
+category = "fail"
+
+# check: fn main() -> Vec<u64> {
+# nextln: $()returning raw_ptrs are not allowed for main()