diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl
index c470b6473..cab7f84d6 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl
@@ -41,7 +41,7 @@ function DI.value_and_pushforward(
             map(first_unwrap, contexts, prep.context_tangents)...,
         )
         y = first(y_and_dy)
-        dy = _copy_output(last(y_and_dy))
+        dy = _maybe_to_primal(last(y_and_dy), y)
         return y, dy
     end
     y = _copy_output(first(ys_and_ty[1]))
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_twoarg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_twoarg.jl
index 3c75f530b..8ebb6ef99 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_twoarg.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_twoarg.jl
@@ -55,7 +55,7 @@ function DI.value_and_pushforward(
             (x, dx),
             map(first_unwrap, contexts, prep.context_tangents)...,
         )
-        return _copy_output(new_dy)
+        return _maybe_to_primal(new_dy, y)
     end
     return y, ty
 end
@@ -93,7 +93,7 @@ function DI.value_and_pushforward!(
             (x, dx),
             map(first_unwrap, contexts, prep.context_tangents)...,
         )
-        copyto!(dy, new_dy)
+        copyto!(dy, _maybe_to_primal(new_dy, y))
     end
     return y, ty
 end
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/onearg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/onearg.jl
index 2514cdc40..2bbf49f1c 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/onearg.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/onearg.jl
@@ -35,7 +35,7 @@ function DI.value_and_pullback(
     new_y, (_, new_dx) = value_and_pullback!!(
         prep.cache, dy, f, x, map(DI.unwrap, contexts)...; prep.args_to_zero
     )
-    return new_y, (_copy_output(new_dx),)
+    return new_y, (_maybe_to_primal(new_dx, x),)
 end
 
 function DI.value_and_pullback(
@@ -51,7 +51,7 @@ function DI.value_and_pullback(
         y, (_, new_dx) = value_and_pullback!!(
             prep.cache, dy, f, x, map(DI.unwrap, contexts)...; prep.args_to_zero
         )
-        y, _copy_output(new_dx)
+        y, _maybe_to_primal(new_dx, x)
     end
     y = first(ys_and_tx[1])
     tx = map(last, ys_and_tx)
@@ -134,7 +134,7 @@ function DI.value_and_gradient(
         prep.cache, f, x, map(DI.unwrap, contexts)...;
         prep.args_to_zero
     )
-    return y, _copy_output(new_grad)
+    return y, _maybe_to_primal(new_grad, x)
 end
 
 function DI.value_and_gradient!(
@@ -150,7 +150,7 @@ function DI.value_and_gradient!(
         prep.cache, f, x, map(DI.unwrap, contexts)...;
         prep.args_to_zero
     )
-    copyto!(grad, new_grad)
+    copyto!(grad, _maybe_to_primal(new_grad, x))
     return y, grad
 end
 
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/twoarg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/twoarg.jl
index 2b55131b9..ed7f4ca9c 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/twoarg.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/twoarg.jl
@@ -64,7 +64,7 @@ function DI.value_and_pullback(
         prep.args_to_zero
     )
     copyto!(y, y_after)
-    return y, (_copy_output(dx),)
+    return y, (_maybe_to_primal(dx, x),)
 end
 
 function DI.value_and_pullback(
@@ -90,7 +90,7 @@ function DI.value_and_pullback(
             prep.args_to_zero
         )
         copyto!(y, y_after)
-        _copy_output(dx)
+        _maybe_to_primal(dx, x)
     end
     return y, tx
 end
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl
index b22d8d49b..beeb6f611 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl
@@ -11,9 +11,41 @@ end
 
 function zero_tangent_or_primal(x, backend::AnyAutoMooncake)
     if get_config(backend).friendly_tangents
-        # zero(x) but safer
-        return tangent_to_primal!!(_copy_output(x), zero_tangent(x))
+        # Mooncake 0.5.25+ replaced `tangent_to_primal!!` with the
+        # `tangent_to_friendly!!` framework. For this internal backup we still
+        # need a primal-shaped value, so use the `AsPrimal` path when
+        # available and fall back for older Mooncake releases.
+        return tangent_to_user_primal(zero_tangent(x), x)
     else
         return zero_tangent(x)
     end
 end
+
+# Safety net: if Mooncake returns a raw Tangent (e.g. Julia 1.11 + StaticArrays),
+# convert it to a primal-shaped value. No-op for already-converted results.
+_maybe_to_primal(tx, x) = _copy_output(tx)
+_maybe_to_primal(tx::Mooncake.Tangent, x) = tangent_to_user_primal(tx, x)
+_maybe_to_primal(tx::Mooncake.MutableTangent, x) = tangent_to_user_primal(tx, x)
+
+@inline maybe_getfield(mod, name::Symbol) =
+    isdefined(mod, name) ? getfield(mod, name) : nothing
+
+const mooncake_tangent_to_friendly = maybe_getfield(
+    Mooncake, Symbol("tangent_to_friendly!!")
+)
+const mooncake_friendly_tangent_cache = maybe_getfield(Mooncake, :FriendlyTangentCache)
+const mooncake_as_primal = maybe_getfield(Mooncake, :AsPrimal)
+const mooncake_no_cache = maybe_getfield(Mooncake, :NoCache)
+
+function tangent_to_user_primal(tx, x)
+    if !isnothing(mooncake_tangent_to_friendly) &&
+            !isnothing(mooncake_friendly_tangent_cache) &&
+            !isnothing(mooncake_as_primal) &&
+            !isnothing(mooncake_no_cache)
+        dest = mooncake_friendly_tangent_cache{mooncake_as_primal}(_copy_output(x))
+        cache = isbitstype(typeof(x)) ? mooncake_no_cache() : IdDict{Any, Any}()
+        return mooncake_tangent_to_friendly(dest, x, tx, cache)
+    else
+        return tangent_to_primal!!(_copy_output(x), tx)
+    end
+end
diff --git a/DifferentiationInterface/test/Back/Mooncake/test.jl b/DifferentiationInterface/test/Back/Mooncake/test.jl
index d531e542a..313c0d2bf 100644
--- a/DifferentiationInterface/test/Back/Mooncake/test.jl
+++ b/DifferentiationInterface/test/Back/Mooncake/test.jl
@@ -1,6 +1,7 @@
 include("../../testutils.jl")
 
 using DifferentiationInterface, DifferentiationInterfaceTest
+using LinearAlgebra: Hermitian, SymTridiagonal, Symmetric
 using Mooncake: Mooncake
 using Test
 
@@ -78,5 +79,36 @@ test_differentiation(
     backends[3:4],
     nomatrix(static_scenarios());
     logging = LOGGING,
-    excluded = SECOND_ORDER
+    excluded = SECOND_ORDER,
 )
+
+@testset "Friendly tangents structured matrices" begin
+    backend = AutoMooncake(; config = Mooncake.Config(; friendly_tangents = true))
+    inputs = (
+        Symmetric([2.0 1.0; 1.0 3.0]),
+        Hermitian(ComplexF64[2 1 + im; 1 - im 3]),
+        SymTridiagonal([2.0, 3.0, 4.0], [5.0, 6.0]),
+    )
+    f(x) = real(sum(abs2, x))
+
+    @testset "$(typeof(x))" for x in inputs
+        grad = gradient(f, backend, x)
+        y, grad2 = value_and_gradient(f, backend, x)
+        pb = only(pullback(identity, backend, x, (x,)))
+
+        @test grad isa Matrix
+        @test grad2 isa Matrix
+        @test pb isa Matrix
+        @test grad == grad2
+        @test y == f(x)
+        @test pb == Matrix(x)
+
+        grad_dense = zero(Matrix(x))
+        @test gradient!(f, grad_dense, backend, x) === grad_dense
+        @test grad_dense == grad
+
+        tx_dense = (zero(Matrix(x)),)
+        @test only(pullback!(identity, tx_dense, backend, x, (x,))) === tx_dense[1]
+        @test tx_dense[1] == pb
+    end
+end