diff --git a/content/best-practices/dos-donts.md b/content/best-practices/dos-donts.md
index 5b3184b0..064c1598 100644
--- a/content/best-practices/dos-donts.md
+++ b/content/best-practices/dos-donts.md
@@ -142,7 +142,9 @@ If you plan to use `Any`, first double-check if extensions can satisfy the use
 case instead. If yes, prefer using extensions.
 
 `Any` was created in Proto3 to replace extensions. However, it has a number of
-design flaws. For most use cases, prefer using extensions.
+design flaws (see
+[We Prefer Extensions Over Any](/design-decisions/extensions-over-any)).
+For most use cases, prefer using extensions.
 
 The main use case that `Any` fulfills is the uncommon scenario in which
 horizontal infrastructure needs to propagate completely arbitrary messages, and
diff --git a/content/design-decisions/_index.md b/content/design-decisions/_index.md
index 4cd5fec9..1d953c33 100644
--- a/content/design-decisions/_index.md
+++ b/content/design-decisions/_index.md
@@ -23,3 +23,5 @@ things develop in the broader ecosystem context.
     Presence](/design-decisions/implicit-presence)
 *   [Insertion Points and Generic
     Services](/design-decisions/insertion-points-and-generic-services)
+*   [Prefer Extensions Over
+    Any](/design-decisions/extensions-over-any)
diff --git a/content/design-decisions/extensions-over-any.md b/content/design-decisions/extensions-over-any.md
new file mode 100644
index 00000000..f94ed7f7
--- /dev/null
+++ b/content/design-decisions/extensions-over-any.md
@@ -0,0 +1,361 @@
+
+
++++
+title = "We Prefer Extensions Over Any"
+weight = 93
+description = "Covers why the Protobuf team regrets Any as a replacement for extensions, and why extensions are preferred for most use cases"
+type = "docs"
++++
+
+When proto3 was introduced, it removed general-purpose
+[extensions](/programming-guides/editions#extensions)
+(keeping them only for custom options) and introduced
+[`google.protobuf.Any`](/programming-guides/editions#any)
+as their replacement.
+
+Unfortunately, `Any` has enough design flaws that that this is a decision the
+Protobuf team regrets. We have no plans to formally deprecate `Any`, and it
+remains supported, but we recommend using extensions instead of `Any` for nearly
+all use cases.
+
+*   [Protobuf Editions](/editions/overview) restored full
+    support for extensions starting in Edition 2023.
+*   For new schemas, **prefer extensions over `Any`** whenever extensions can
+    satisfy the use case (see [Proto Best
+    Practices](/best-practices/dos-donts#avoid-any)).
+*   Reserve `Any` for the uncommon case where horizontal infrastructure needs to
+    propagate completely arbitrary messages and declaring an extension for each
+    possible type is infeasible.
+
+## What Extensions and `Any` Are {#what}
+
+Both mechanisms solve the same dependency problem: letting a container message
+carry a submessage whose `.proto` file the container does not import. Instead of
+the container depending on every possible payload type, each payload depends on
+the container.
+
+### Extensions {#what-extensions}
+
+An [extension](/programming-guides/editions#extensions)
+is a field defined outside of its container message, using a field number from
+an `extensions` range reserved by the container:
+
+```proto
+// media/user_content.proto
+edition = "2024";
+
+package media;
+
+message UserContent {
+  string id = 1;
+
+  extensions 100 to 199 [
+    declaration = {
+      number: 100,
+      full_name: ".kittens.kitten_video",
+      type: ".kittens.Video"
+    }
+  ];
+}
+```
+
+```proto
+// kittens/video_ext.proto
+edition = "2024";
+
+package kittens;
+
+import "kittens/video.proto";
+import "media/user_content.proto";
+
+extend media.UserContent {
+  Video kitten_video = 100;
+}
+```
+
+In generated code, the extension is accessed as a typed submessage stored
+directly on the parent message:
+
+```cpp
+media::UserContent content;
+content.MutableExtension(kittens::kitten_video)->set_title("Cute kittens");
+
+if (content.HasExtension(kittens::kitten_video)) {
+  const kittens::Video& video = content.GetExtension(kittens::kitten_video);
+}
+```
+
+On the wire, an extension is identical to a regular field with the same field
+number, type, and cardinality. With [extension
+declarations](/programming-guides/extension_declarations),
+the container can list the number, name, and type name of each extension in one
+place without importing the payload `.proto` file.
+
+### `google.protobuf.Any` {#what-any}
+
+[`google.protobuf.Any`](/reference/protobuf/google.protobuf#any)
+is a wrapper message defined in `google/protobuf/any.proto`:
+
+```proto
+syntax = "proto3";
+
+package google.protobuf;
+
+message Any {
+  string type_url = 1;
+  bytes value = 2;
+}
+```
+
+Instead of extending the container message, the container declares a field of
+type `google.protobuf.Any`. Packing a message into `Any` serializes the inner
+message into `value` and writes a URI containing the inner message's fully
+qualified name into `type_url`:
+
+```cpp
+media::UserContent content;
+kittens::Video video;
+video.set_title("Cute kittens");
+content.mutable_payload()->PackFrom(video);
+
+if (content.payload().Is<kittens::Video>()) {
+  kittens::Video unpacked;
+  if (content.payload().UnpackTo(&unpacked)) {
+    // use unpacked
+  }
+}
+```
+
+## Why Proto3 Replaced Extensions with `Any` {#why-introduced}
+
+In proto2, extensions had two real problems:
+
+1.  There was no built-in way to coordinate extension numbers on a container
+    message without importing the extensions. Because `extend` blocks lived in
+    separate `.proto` files, two teams could pick the same field number on a
+    shared container message and silently collide on the wire.
+2.  Proto3 tried to simplify the language so that new runtimes could represent
+    messages as plain [open
+    structs](/design-decisions/opaque-apis) with minimal
+    runtime machinery. Extensions required an `ExtensionRegistry`, extension
+    storage on messages, and parameterized accessor APIs in every language.
+
+`Any` avoided both: on the binary wire it is an ordinary message with a `string`
+and a `bytes` field, its discriminator is the globally unique message name
+rather than a coordinated field number, and runtime support could be limited to
+`PackFrom` / `UnpackTo` helpers plus special-case handling in
+[ProtoJSON](/programming-guides/json#any) and TextFormat.
+
+The open-struct premise was abandoned (see [We Prefer Opaque
+APIs](/design-decisions/opaque-apis)).
+
+Risks of extension number collisions are still a concern with extensions, but
+can be mitigated in most cases by using [extension
+declarations](/programming-guides/extension_declarations).
+
+## Why We Regret `Any` as a Replacement for Extensions {#flaws}
+
+### Type Names on the Binary Wire Prevent Renaming and Repackaging {#type-url-lock-in}
+
+A core property of the Protobuf binary wire format is that message names, field
+names, and package names do not appear on the wire. Because the binary format
+identifies fields by numeric tag, you can rename a field, rename a message, or
+move a message to a different `.proto` package without breaking wire
+compatibility with deployed binaries or stored data.
+
+`Any` breaks this property. Because `PackFrom()` writes the fully qualified
+message name into `type_url` on the binary wire, **any message packed into an
+`Any` cannot safely be renamed or moved to a different `.proto` package**:
+
+*   If a message is renamed or moved to a new package, `Is<T>()` and
+    `UnpackTo()` compare the new descriptor's `full_name()` against the old
+    `type_url` string and reject existing payloads, even though the serialized
+    bytes in `value` are wire-compatible.
+*   At the same time, new binaries start writing the new `type_url` string,
+    which older binaries and rollback targets do not recognize.
+
+Worse, **`Any` is not opt-in**. A message author does not declare that their
+message may be packed into an `Any`. Any caller in another repository or service
+can pass an arbitrary message to `PackFrom()` without the message owner's
+knowledge, and because packing can happen through generic or reflective code
+paths, static analysis cannot prove that a message type is never stored in an
+`Any`. This is a very spooky property that makes it difficult to know if
+renaming a message might not be safe.
+
+Extensions identify fields on the wire by their numeric tag, just like regular
+fields. Renaming an extension, renaming the message type it holds, or moving
+either across `.proto` packages is safe on the binary wire.
+
+### Wire Incompatibility with Regular Fields {#wire-incompatibility}
+
+An extension has the exact same binary wire encoding as a regular field with the
+same field number, type, and cardinality. That makes the boundary between
+regular fields and extensions reversible:
+
+*   If a regular field on a container message is causing unwanted build
+    dependencies, it can be moved out into an `extend` block with the same field
+    number and type without changing a single byte on the wire.
+*   Conversely, a widely used extension can be promoted directly into a regular
+    field on the container message.
+
+`Any` wraps its payload inside a submessage containing `type_url` (field 1) and
+`value` (field 2). It is wire-incompatible with a normal submessage field, so a
+field cannot be migrated into or out of an `Any` without breaking the wire
+format.
+
+### Wire Size Overhead {#wire-size}
+
+An extension tag on the wire is a single varint encoding the field number and
+wire type: 2 bytes for field numbers up to 2047, and at most 5 bytes for the
+largest valid field numbers.
+
+Every `Any` message carries the full `type.googleapis.com/package.MessageName`
+string on the wire in addition to the nested length prefixes. A typical
+`type_url` adds 40 to 80 bytes per instance. For small messages or `repeated
+google.protobuf.Any` fields, the repeated `type_url` strings often take more
+space than the payload itself.
+
+### In-Memory Cost and Eager Serialization {#serialization}
+
+Because `Any` stores its payload as a `bytes value` field rather than as a typed
+submessage in the message tree, working with `Any` in memory is clumsy and
+expensive:
+
+*   `PackFrom()` immediately serializes the inner message into a `bytes` buffer,
+    even if the outer message is only passed around in memory.
+*   In most languages (including C++, Go, Python, and open-source Java), calling
+    `UnpackTo()` allocates a separate message object and parses `value` from
+    scratch on every read, unless the caller maintains a separate cache by hand.
+    By contrast, an extension is stored directly inside the parent message (and
+    shares its arena in C++), so reading `GetExtension()` is a pointer lookup.
+
+A common misconception is that `Any` is cheaper for intermediate proxies that do
+not care about the payload because `value` stays unparsed until `UnpackTo()` is
+called. Extensions already have this property: if a binary does not link in or
+register an extension, the bytes remain unparsed in the unknown field set and
+are forwarded intact on serialization. Even when a binary *does* link in the
+extension, runtimes that support lazy fields defer parsing the extension until
+the first `GetExtension()` call and then cache the parsed submessage in place.
+
+### Broken `MergeFrom`, Equality, and Reflection Semantics {#semantics}
+
+To Protobuf, an `Any` is just a two-field message (`string type_url = 1; bytes
+value = 2;`), not a typed container. Standard message operations act on those
+two scalar fields rather than on the packed message inside:
+
+#### `MergeFrom` {#merging}
+
+When two messages with a submessage extension are merged via `MergeFrom()`, the
+extension submessages are merged recursively field by field, and distinct
+extensions on the same container coexist.
+
+When two `Any` messages are merged, `MergeFrom()` merges `type_url` and `value`
+as ordinary scalar fields, overwriting `value` instead of merging the inner
+message. Worse, because `google/protobuf/any.proto` is defined with `syntax =
+"proto3"`, both `type_url` and `value` have [implicit
+presence](/design-decisions/implicit-presence#merging):
+
+1.  Suppose `A` is an `Any` packed with a non-empty `Bar` message (`type_url =
+    "type.googleapis.com/Bar"`, `value = "\x08\x01"`).
+2.  Suppose `B` is an `Any` packed with a default, empty `Quux` message. Because
+    an all-default message serializes to 0 bytes, `B` has `type_url =
+    "type.googleapis.com/Quux"` and `value = ""`.
+3.  Calling `A.MergeFrom(B)` overwrites `A.type_url` with
+    `"type.googleapis.com/Quux"`, but because `B.value` is empty (`""`),
+    implicit presence treats `B.value` as unset and does not overwrite
+    `A.value`.
+
+The merged `Any` now has `Quux`'s `type_url` paired with `Bar`'s serialized wire
+bytes.
+
+#### Equality {#equality}
+
+Standard message equality on `Any` compares the raw `value` byte string rather
+than the logical inner message. As explained in [Serialization Is Not
+Canonical](/programming-guides/serialization-not-canonical),
+two logically equal Protobuf messages can serialize to different byte sequences
+(for example, due to map entry ordering or unknown fields), causing two `Any`
+messages holding equivalent payloads to compare unequal.
+
+#### Reflection and Generic Traversal {#reflection}
+
+Unless a tool links in the packed message's descriptor and writes custom
+`Any`-unpacking code, reflection walkers, field-path utilities, and redaction
+passes only see a `string type_url` and an opaque `bytes value`. Extensions have
+normal `FieldDescriptor` entries and are visited by standard reflection walkers
+without special cases.
+
+### Poor Fit for Mobile and Lite Runtimes {#lite}
+
+In mobile, embedded, and web client builds (`LITE_RUNTIME`), Protobuf strips
+descriptors and symbol names to reduce binary size and avoid leaking unreleased
+feature names in shipped client binaries.
+
+`Any` relies on runtime type names to construct and check `type_url`:
+
+*   In **JavaLite**, `MessageLite` does not carry descriptor names, so
+    `Any.pack()`, `Any.unpack()`, and `Any.is()` are omitted from the generated
+    `Any` class altogether. Callers must construct and compare `type_url`
+    strings manually.
+*   In **C++ Lite**, `Any::PackFrom<T>()` and `UnpackTo<T>()` only work because
+    the code generator emits a `FullMessageName()` string literal on every
+    message class, which forces the binary to retain the `.proto` package and
+    message name for every type used with `Any`.
+
+Extensions use numeric tags and generated extension identifiers, which work in
+`LITE_RUNTIME` builds and support tree shaking without retaining descriptor
+strings.
+
+### Type URLs Do Not Provide Dynamic Schema Discovery {#type-urls}
+
+The `type_url` field was originally formatted as a URL
+(`type.googleapis.com/...`) on the theory that runtimes might fetch unknown
+schemas over HTTP at parse time. Protobuf never implemented remote type fetching
+and explicitly warns against contacting `type_url` endpoints in `any.proto` as a
+security problem. Every parser simply strips everything up to the last `/`, and
+unpacking an `Any` in JSON, TextFormat, or reflection still requires the target
+descriptor to be linked or loaded into the local binary's descriptor pool, just
+like an extension.
+
+## What to Use Instead {#instead}
+
+### Regular Submessage Fields or `oneof` {#oneof}
+
+When the set of possible payload types is bounded, known to the container
+author, and importing them directly into the container `.proto` does not cause
+dependency problems, use a regular submessage field or a `oneof`. A `oneof`
+makes the set of alternatives explicit in one place and generates the cleanest
+API in every language.
+
+### Extensions with Extension Declarations {#use-extensions}
+
+When payload definitions need to live in separate `.proto` files so the
+container does not depend on them, use
+[extensions](/programming-guides/editions#extensions):
+
+*   Add [extension
+    declarations](/programming-guides/extension_declarations)
+    to the container's `extensions` range so all allocated extension numbers and
+    type names are listed in one place and checked by `protoc` without importing
+    the payload `.proto` files.
+*   If central code-review ownership on the container `.proto` file would be a
+    bottleneck for teams adding extensions, put the extendable container (or a
+    dedicated extension-carrier submessage) in a separate `.proto` file with
+    broader ownership.
+*   If your container message is currently in a `syntax = "proto3"` file (which
+    does not allow `extensions` ranges), migrate that file to [Protobuf
+    Editions](/editions/overview). Moving a file from
+    `proto3` to Edition 2023 is wire-compatible, and remaining `proto3` files
+    can still import it.
+
+### When `Any` Is Still Appropriate {#when-any}
+
+The one case where `Any` is still the right tool is **unbounded horizontal
+infrastructure**: systems that transport, log, or store completely arbitrary
+messages across independent domains (for example, a generic RPC error detail
+list like `google.rpc.Status.details`, a generic task queue payload, or a dead
+letter queue) where declaring an extension on the envelope for every message
+type in the ecosystem is infeasible.
+
+Whenever you do use `Any`, treat the package name and message name of every
+packed message as a permanently frozen part of your wire protocol.
diff --git a/content/programming-guides/editions.md b/content/programming-guides/editions.md
index ebadf834..be8eeb85 100644
--- a/content/programming-guides/editions.md
+++ b/content/programming-guides/editions.md
@@ -1510,7 +1510,8 @@ If you want to limit contained messages to a small number of types and to
 require permission before adding new types to the list, consider using
 [extensions](#extensions) with
 [extension declarations](/programming-guides/extension_declarations)
-instead of `Any` message types.
+instead of `Any` message types. For most use cases,
+[we prefer extensions over `Any`](/design-decisions/extensions-over-any).
 
 ## Oneof {#oneof}
 
diff --git a/content/reference/protobuf/google.protobuf.md b/content/reference/protobuf/google.protobuf.md
index 28d5445e..8f49edd0 100644
--- a/content/reference/protobuf/google.protobuf.md
+++ b/content/reference/protobuf/google.protobuf.md
@@ -50,7 +50,7 @@ In most cases, there are better options:
 
 *   For new messages, it's better to use regular explicit-presence fields
     (`optional` in proto2/proto3, regular field in edition >= 2023).
-*   Extensions are generally a better option than `Any` fields.
+*   [Extensions are generally a better option than `Any` fields](/design-decisions/extensions-over-any).
 
 ## Any {#any}