diff --git a/include/boost/json/impl/monotonic_resource.ipp b/include/boost/json/impl/monotonic_resource.ipp
index 56728b1e1..7730faaef 100644
--- a/include/boost/json/impl/monotonic_resource.ipp
+++ b/include/boost/json/impl/monotonic_resource.ipp
@@ -14,8 +14,10 @@
 #include <boost/json/monotonic_resource.hpp>
 #include <boost/json/detail/except.hpp>
 #include <boost/core/max_align.hpp>
+#include <boost/throw_exception.hpp>
 
 #include <memory>
+#include <new>
 
 namespace boost {
 namespace json {
@@ -128,8 +130,15 @@ do_allocate(
         return p;
     }
 
-    if(next_size_ < n)
-        next_size_ = round_pow2(n);
+    // a new block is only aligned to alignof(block), so an
+    // over-aligned request may need up to align - alignof(block)
+    // bytes of padding in addition to n
+    std::size_t const pad = align > alignof(block)
+        ? align - alignof(block) : 0;
+    if(n > max_size() - pad)
+        throw_exception( std::bad_alloc(), BOOST_CURRENT_LOCATION );
+    if(next_size_ < n + pad)
+        next_size_ = round_pow2(n + pad);
     auto b = ::new(upstream_->allocate(
         sizeof(block) + next_size_)) block;
     b->p = b + 1;
diff --git a/test/monotonic_resource.cpp b/test/monotonic_resource.cpp
index d682b9350..e5d192fd5 100644
--- a/test/monotonic_resource.cpp
+++ b/test/monotonic_resource.cpp
@@ -17,6 +17,7 @@
 #include <boost/json/serialize.hpp>
 #include <boost/core/max_align.hpp>
 #include <iostream>
+#include <new>
 
 #include "checking_resource.hpp"
 #include "test_suite.hpp"
@@ -317,6 +318,29 @@ R"xx({
         (void)mr.allocate(1, alignof(core::max_align_t));
     }
 
+    void
+    testOverAligned()
+    {
+        // an over-aligned request that fills a fresh block needs
+        // room for the padding in addition to the requested size
+        for(std::size_t align = 2 * alignof(core::max_align_t);
+            align <= 4096; align *= 2)
+        {
+            monotonic_resource mr;
+            void* p = mr.allocate(1024, align);
+            BOOST_TEST(p != nullptr);
+            BOOST_TEST(
+                !(reinterpret_cast<std::uintptr_t>(p) % align));
+        }
+        // the padding must not make the request overflow
+        {
+            monotonic_resource mr;
+            BOOST_TEST_THROWS(
+                mr.allocate(std::size_t(-1) - 100, 4096),
+                std::bad_alloc);
+        }
+    }
+
     void
     run()
     {
@@ -324,6 +348,7 @@ R"xx({
         testStorage();
         testGeneral();
         testAllocation();
+        testOverAligned();
     }
 };