diff --git a/.chronus/changes/fix-optional-prop-required-2024-4-6-21-39-1.md b/.chronus/changes/fix-optional-prop-required-2024-4-6-21-39-1.md
new file mode 100644
index 0000000000..5d92ac5e75
--- /dev/null
+++ b/.chronus/changes/fix-optional-prop-required-2024-4-6-21-39-1.md
@@ -0,0 +1,8 @@
+---
+# Change versionKind to one of: internal, fix, dependencies, feature, deprecation, breaking
+changeKind: fix
+packages:
+  - "@typespec/compiler"
+---
+
+Model with an optional property should not be satisfy a constraint with that property required. (`{foo?: string}` cannot be assigned to a constraint of `{foo: string}`)
diff --git a/packages/compiler/src/core/checker.ts b/packages/compiler/src/core/checker.ts
index a693f612f8..9af59b7d52 100644
--- a/packages/compiler/src/core/checker.ts
+++ b/packages/compiler/src/core/checker.ts
@@ -5785,6 +5785,18 @@ export function createChecker(program: Program): Checker {
       } else {
         remainingProperties.delete(prop.name);
 
+        if (sourceProperty.optional && !prop.optional) {
+          diagnostics.push(
+            createDiagnostic({
+              code: "property-required",
+              format: {
+                propName: prop.name,
+                targetType: getTypeName(target),
+              },
+              target: diagnosticTarget,
+            })
+          );
+        }
         const [related, propDiagnostics] = isTypeAssignableToInternal(
           sourceProperty.type,
           prop.type,
diff --git a/packages/compiler/src/core/messages.ts b/packages/compiler/src/core/messages.ts
index b7311898ed..51fa9ffcda 100644
--- a/packages/compiler/src/core/messages.ts
+++ b/packages/compiler/src/core/messages.ts
@@ -404,6 +404,12 @@ const diagnostics = {
       withDetails: paramMessage`Type '${"sourceType"}' is not assignable to type '${"targetType"}'\n  ${"details"}`,
     },
   },
+  "property-required": {
+    severity: "error",
+    messages: {
+      default: paramMessage`Property '${"propName"}' is required in type '${"targetType"}' but here is optional.`,
+    },
+  },
   "no-prop": {
     severity: "error",
     messages: {
diff --git a/packages/compiler/test/checker/relation.test.ts b/packages/compiler/test/checker/relation.test.ts
index ba66144a2a..20b13217a5 100644
--- a/packages/compiler/test/checker/relation.test.ts
+++ b/packages/compiler/test/checker/relation.test.ts
@@ -737,6 +737,16 @@ describe("compiler: checker: type relations", () => {
       });
     });
 
+    it("emit diagnostic when optional property is assigned to required", async () => {
+      await expectTypeNotAssignable(
+        { source: `{foo?: string}`, target: `{foo: string}` },
+        {
+          code: "property-required",
+          message: "Property 'foo' is required in type '(anonymous model)' but here is optional.",
+        }
+      );
+    });
+
     it("emit diagnostic when required property is missing", async () => {
       await expectTypeNotAssignable(
         { source: `{foo: "abc"}`, target: `{foo: string, bar: string}` },