diff --git a/upstream_utils/drake-dllexport-dare.patch b/upstream_utils/drake-dllexport-dare.patch
new file mode 100644
index 0000000000..9e5fb00cd7
--- /dev/null
+++ b/upstream_utils/drake-dllexport-dare.patch
@@ -0,0 +1,28 @@
+diff --git b/wpimath/src/main/native/include/drake/math/discrete_algebraic_riccati_equation.h a/wpimath/src/main/native/include/drake/math/discrete_algebraic_riccati_equation.h
+index cb0a4ee13..5d7a316f3 100644
+--- b/wpimath/src/main/native/include/drake/math/discrete_algebraic_riccati_equation.h
++++ a/wpimath/src/main/native/include/drake/math/discrete_algebraic_riccati_equation.h
+@@ -4,6 +4,7 @@
+ #include <cstdlib>
+ 
+ #include <Eigen/Core>
++#include <wpi/SymbolExports.h>
+ 
+ namespace drake {
+ namespace math {
+@@ -20,6 +21,7 @@ namespace math {
+ /// "On the Numerical Solution of the Discrete-Time Algebraic Riccati Equation"
+ /// by Thrasyvoulos Pappas, Alan J. Laub, and Nils R. Sandell
+ ///
++WPILIB_DLLEXPORT
+ Eigen::MatrixXd DiscreteAlgebraicRiccatiEquation(
+     const Eigen::Ref<const Eigen::MatrixXd>& A,
+     const Eigen::Ref<const Eigen::MatrixXd>& B,
+@@ -69,6 +71,7 @@ Eigen::MatrixXd DiscreteAlgebraicRiccatiEquation(
+ /// @throws std::runtime_error if Q − NR⁻¹Nᵀ is not positive semi-definite.
+ /// @throws std::runtime_error if R is not positive definite.
+ ///
++WPILIB_DLLEXPORT
+ Eigen::MatrixXd DiscreteAlgebraicRiccatiEquation(
+     const Eigen::Ref<const Eigen::MatrixXd>& A,
+     const Eigen::Ref<const Eigen::MatrixXd>& B,
diff --git a/upstream_utils/update_drake.py b/upstream_utils/update_drake.py
index 4f7fa6b467..246857a473 100755
--- a/upstream_utils/update_drake.py
+++ b/upstream_utils/update_drake.py
@@ -8,7 +8,7 @@ from upstream_utils import setup_upstream_repo, comment_out_invalid_includes, wa
 
 def main():
     root, repo = setup_upstream_repo("https://github.com/RobotLocomotion/drake",
-                                     "v0.33.0")
+                                     "v0.34.0")
     wpimath = os.path.join(root, "wpimath")
 
     # Delete old install
@@ -61,7 +61,10 @@ def main():
             os.path.join(wpimath, "src/test/native/include")
         ])
 
-    apply_patches(root, ["upstream_utils/drake-replace-dense-with-core.patch"])
+    apply_patches(root, [
+        "upstream_utils/drake-dllexport-dare.patch",
+        "upstream_utils/drake-replace-dense-with-core.patch"
+    ])
 
 
 if __name__ == "__main__":
diff --git a/wpimath/src/main/native/include/drake/common/drake_assert.h b/wpimath/src/main/native/include/drake/common/drake_assert.h
index 51fdfad468..88587fad79 100644
--- a/wpimath/src/main/native/include/drake/common/drake_assert.h
+++ b/wpimath/src/main/native/include/drake/common/drake_assert.h
@@ -88,6 +88,14 @@ namespace internal {
 // Report an assertion failure; will either Abort(...) or throw.
 [[noreturn]] void AssertionFailed(const char* condition, const char* func,
                                   const char* file, int line);
+template <bool>
+constexpr void DrakeAssertWasUsedWithRawPointer() {}
+template<>
+[[deprecated("\nDRAKE DEPRECATED: When using DRAKE_ASSERT or DRAKE_DEMAND on"
+" a raw pointer, always write out DRAKE_ASSERT(foo != nullptr), do not write"
+" DRAKE_ASSERT(foo) and rely on implicit pointer-to-bool conversion."
+"\nThe deprecated code will be removed from Drake on or after 2021-12-01.")]]
+constexpr void DrakeAssertWasUsedWithRawPointer<true>() {}
 }  // namespace internal
 namespace assert {
 // Allows for specialization of how to bool-convert Conditions used in
@@ -114,6 +122,8 @@ struct ConditionTraits {
     typedef ::drake::assert::ConditionTraits<                                \
         typename std::remove_cv_t<decltype(condition)>> Trait;               \
     static_assert(Trait::is_valid, "Condition should be bool-convertible."); \
+    ::drake::internal::DrakeAssertWasUsedWithRawPointer<                     \
+        std::is_pointer_v<decltype(condition)>>();                           \
     if (!Trait::Evaluate(condition)) {                                       \
       ::drake::internal::AssertionFailed(                                    \
            #condition, __func__, __FILE__, __LINE__);                        \
@@ -139,10 +149,14 @@ namespace drake {
 constexpr bool kDrakeAssertIsArmed = false;
 constexpr bool kDrakeAssertIsDisarmed = true;
 }  // namespace drake
-# define DRAKE_ASSERT(condition) static_assert(                        \
-    ::drake::assert::ConditionTraits<                                  \
-        typename std::remove_cv_t<decltype(condition)>>::is_valid,     \
-    "Condition should be bool-convertible.");
+# define DRAKE_ASSERT(condition) do {                                  \
+    static_assert(                                                     \
+        ::drake::assert::ConditionTraits<                              \
+            typename std::remove_cv_t<decltype(condition)>>::is_valid, \
+        "Condition should be bool-convertible.");                      \
+    ::drake::internal::DrakeAssertWasUsedWithRawPointer<               \
+        std::is_pointer_v<decltype(condition)>>();                     \
+  } while (0)
 # define DRAKE_ASSERT_VOID(expression) static_assert(           \
     std::is_convertible_v<decltype(expression), void>,          \
     "Expression should be void.")