diff --git a/DifferentiationInterface/Project.toml b/DifferentiationInterface/Project.toml
index d4058e7ac..40d96972c 100644
--- a/DifferentiationInterface/Project.toml
+++ b/DifferentiationInterface/Project.toml
@@ -42,6 +42,7 @@ DifferentiationInterfaceForwardDiffExt = ["ForwardDiff", "DiffResults"]
 DifferentiationInterfaceGPUArraysCoreExt = ["GPUArraysCore", "Adapt"]
 DifferentiationInterfaceGTPSAExt = "GTPSA"
 DifferentiationInterfaceMooncakeExt = "Mooncake"
+DifferentiationInterfaceMooncakeStaticArraysExt = ["Mooncake", "StaticArrays"]
 DifferentiationInterfacePolyesterForwardDiffExt = [
     "PolyesterForwardDiff",
     "ForwardDiff",
@@ -71,7 +72,7 @@ ForwardDiff = "0.10.36,1"
 GPUArraysCore = "0.2"
 GTPSA = "1.4.0"
 LinearAlgebra = "1"
-Mooncake = "0.5.1"
+Mooncake = "0.5.27"
 PolyesterForwardDiff = "0.1.2"
 ReverseDiff = "1.15.1"
 SparseArrays = "1"
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/DifferentiationInterfaceMooncakeExt.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/DifferentiationInterfaceMooncakeExt.jl
index 3513d548c..8d1fc46f3 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/DifferentiationInterfaceMooncakeExt.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/DifferentiationInterfaceMooncakeExt.jl
@@ -30,7 +30,7 @@ using Mooncake:
     primal,
     _copy_output,
     _copy_to_output!!,
-    tangent_to_primal!!
+    tangent_to_friendly!!
 
 const AnyAutoMooncake{C} = Union{AutoMooncake{C}, AutoMooncakeForward{C}}
 
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl
index c470b6473..447f84b6b 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/forward_onearg.jl
@@ -41,7 +41,8 @@ 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_raw = last(y_and_dy)
+        dy = @something(_to_friendly_value(dy_raw, y), _copy_output(dy_raw))
         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..a6354a0f7 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 @something(_to_friendly_value(new_dy, y), _copy_output(new_dy))
     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, something(_to_friendly_value(new_dy, y), new_dy))
     end
     return y, ty
 end
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/onearg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/onearg.jl
index 2514cdc40..61f5eb837 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, (@something(_to_friendly_value(new_dx, x), _copy_output(new_dx)),)
 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, @something(_to_friendly_value(new_dx, x), _copy_output(new_dx))
     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, @something(_to_friendly_value(new_grad, x), _copy_output(new_grad))
 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, something(_to_friendly_value(new_grad, x), new_grad))
     return y, grad
 end
 
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/twoarg.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/twoarg.jl
index 2b55131b9..4dbc6d742 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, (@something(_to_friendly_value(dx, x), _copy_output(dx)),)
 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)
+        @something(_to_friendly_value(dx, x), _copy_output(dx))
     end
     return y, tx
 end
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl
index b22d8d49b..11119face 100644
--- a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeExt/utils.jl
@@ -9,11 +9,19 @@ function call_and_return(f!::F, y, x, contexts...) where {F}
     return y
 end
 
+# Hook for bridging primal types whose `friendly_tangent_cache` falls through to
+# `:as_raw` in Mooncake's framework, leaking a raw `Tangent` / `MutableTangent`
+# instead of a primal-shaped value. The default returns `nothing`; specialised
+# methods are loaded by triple-extensions when the relevant primal-type packages
+# are available (see DifferentiationInterfaceMooncakeStaticArraysExt for the
+# `SArray` / `MArray` case).
+_to_friendly_value(t, x) = nothing
+
 function zero_tangent_or_primal(x, backend::AnyAutoMooncake)
+    zt = zero_tangent(x)
     if get_config(backend).friendly_tangents
-        # zero(x) but safer
-        return tangent_to_primal!!(_copy_output(x), zero_tangent(x))
+        return @something(_to_friendly_value(zt, x), tangent_to_friendly!!(x, zt))
     else
-        return zero_tangent(x)
+        return zt
     end
 end
diff --git a/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeStaticArraysExt/DifferentiationInterfaceMooncakeStaticArraysExt.jl b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeStaticArraysExt/DifferentiationInterfaceMooncakeStaticArraysExt.jl
new file mode 100644
index 000000000..797445b6f
--- /dev/null
+++ b/DifferentiationInterface/ext/DifferentiationInterfaceMooncakeStaticArraysExt/DifferentiationInterfaceMooncakeStaticArraysExt.jl
@@ -0,0 +1,36 @@
+module DifferentiationInterfaceMooncakeStaticArraysExt
+
+using Base: IEEEFloat
+using DifferentiationInterface: DifferentiationInterface
+using Mooncake: Mooncake
+using StaticArrays: MArray, SArray
+
+# Reach into the binary MooncakeExt to extend its `_to_friendly_value` hook.
+# Both Mooncake and StaticArrays are loaded whenever this extension is active,
+# so the binary extension is guaranteed to be loaded as well.
+const _MooncakeExt = Base.get_extension(
+    DifferentiationInterface, :DifferentiationInterfaceMooncakeExt,
+)
+
+# Restrict to scalar float / complex-float eltypes: those are the layouts where
+# Mooncake's framework sends `SArray` / `MArray` through `AsRaw` and the single
+# `data::NTuple` element-to-position mapping is 1:1 (no aliasing). Non-float
+# eltypes hit Mooncake's element-wise `AbstractArray` recursion at
+# `Mooncake/src/tangents/tangents.jl:1453`; let that path run unimpeded.
+const _StaticEltype = Union{IEEEFloat, Complex{<:IEEEFloat}}
+
+# Mooncake's `friendly_tangent_cache` framework defaults to `:as_raw` for
+# `SArray` / `MArray` primals with float eltype, leaking a raw `Tangent` /
+# `MutableTangent` instead of a primal-shaped value. Bridge that gap here. The
+# reconstruction is unambiguous because the `data::NTuple` field maps each
+# element to one logical position (unlike `Symmetric` / `Hermitian`, where a
+# single stored entry can represent two positions).
+@inline _MooncakeExt._to_friendly_value(
+    t::Mooncake.Tangent, x::SArray{S, T}
+) where {S, T <: _StaticEltype} = typeof(x)(Mooncake.val(t.fields.data))
+
+@inline _MooncakeExt._to_friendly_value(
+    t::Mooncake.MutableTangent, x::MArray{S, T}
+) where {S, T <: _StaticEltype} = typeof(x)(Mooncake.val(t.fields.data))
+
+end # module
diff --git a/DifferentiationInterface/test/Back/Mooncake/test.jl b/DifferentiationInterface/test/Back/Mooncake/test.jl
index d531e542a..7555752af 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 +79,110 @@ test_differentiation(
     backends[3:4],
     nomatrix(static_scenarios());
     logging = LOGGING,
-    excluded = SECOND_ORDER
+    excluded = SECOND_ORDER,
 )
+
+@testset "Friendly tangents structured matrices" begin
+    # Mooncake 0.5.25+ returns a plain `Matrix` for structured inputs under
+    # `friendly_tangents=true` (chalk-lab/Mooncake.jl#1103); the complex case
+    # follows the standard reverse-mode convention (chalk-lab/Mooncake.jl#773).
+    #
+    # Per-wrapper test functions are chosen for their non-triviality given
+    # that matmul on small matrices hits a `utf8proc_isupper` ccall that
+    # Mooncake cannot differentiate (LinearAlgebra._matmul2x2_elements →
+    # WrapperChar). For the real wrappers we use a manual triple-loop tr(X^3)
+    # whose unrestricted gradient is 3·X²; for Hermitian we use the simpler
+    # abs2-sum because the complex Wirtinger ground truth via tr(X^3) is
+    # convention-heavy. The expected friendly gradient is then computed by
+    # aggregating the unrestricted per-element gradient into the wrapper's
+    # canonical storage cells, derived independently of Mooncake.
+
+    # tr(X^3) without matmul. Indices i,j,k each range over axes(X,1).
+    function tr_x3(X)
+        s = zero(eltype(X))
+        n = size(X, 1)
+        @inbounds for i in 1:n, j in 1:n, k in 1:n
+            s += X[i, j] * X[j, k] * X[k, i]
+        end
+        return real(s)
+    end
+
+    # Symmetric storage: upper triangle holds the sum of (i,j) and (j,i)
+    # per-element contributions; strict lower triangle is zero.
+    function aggregate_symmetric(G)
+        n = size(G, 1)
+        H = zero(G)
+        @inbounds for i in 1:n
+            H[i, i] = G[i, i]
+            for j in (i + 1):n
+                H[i, j] = G[i, j] + G[j, i]
+            end
+        end
+        return H
+    end
+
+    # SymTridiagonal storage: diagonal + symmetric off-diagonals (both
+    # `(i,i+1)` and `(i+1,i)` slots hold the doubled contribution); entries
+    # outside that band are structurally zero in the wrapper.
+    function aggregate_symtridiagonal(G)
+        n = size(G, 1)
+        H = zero(G)
+        @inbounds for i in 1:n
+            H[i, i] = G[i, i]
+            if i < n
+                aggregated = G[i, i + 1] + G[i + 1, i]
+                H[i, i + 1] = aggregated
+                H[i + 1, i] = aggregated
+            end
+        end
+        return H
+    end
+
+    backend = AutoMooncake(; config = Mooncake.Config(; friendly_tangents = true))
+    abs2_sum(x) = real(sum(abs2, x))
+    cases = (
+        (
+            x = Symmetric([2.0 1.0; 1.0 3.0]),
+            f = tr_x3,
+            expected_grad = let M = Matrix(Symmetric([2.0 1.0; 1.0 3.0]))
+                aggregate_symmetric(3 * M^2)
+            end,
+        ),
+        (
+            x = Hermitian(ComplexF64[2 1 + im; 1 - im 3]),
+            f = abs2_sum,
+            expected_grad = ComplexF64[4 4 + 4im; 0 6],
+        ),
+        (
+            x = SymTridiagonal([2.0, 3.0, 4.0], [5.0, 6.0]),
+            f = tr_x3,
+            expected_grad = let M = Matrix(SymTridiagonal([2.0, 3.0, 4.0], [5.0, 6.0]))
+                aggregate_symtridiagonal(3 * M^2)
+            end,
+        ),
+    )
+
+    @testset "$(typeof(case.x))" for case in cases
+        x = case.x
+        f = case.f
+        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 grad ≈ case.expected_grad
+        @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