diff --git a/BUILD.bazel b/BUILD.bazel
index 33146892a6b8..b0d7d2dd5430 100644
--- a/BUILD.bazel
+++ b/BUILD.bazel
@@ -13,17 +13,21 @@ load("@bazel_gazelle//:def.bzl", "gazelle")
 # gazelle:prefix github.com/cockroachdb/cockroach
 # gazelle:build_file_name BUILD.bazel
 
-# We disable protobuf generation for our dependencies
+# We disable protobuf generation for our dependencies.
 #
 # gazelle:proto disable_global
 
-# Gazelle is unable to resolve this specific package.
+# Gazelle needs the following resolve hints.
 #
 # TODO(irfansharif): I'm not sure why this is. Is it because it's a proto only
 # package?
 #
 # gazelle:resolve go github.com/grpc-ecosystem/grpc-gateway/internal //vendor/github.com/grpc-ecosystem/grpc-gateway/internal
 
+# See pkg/sql/opt/optgen/cmd/langgen/BUILD.bazel for more details.
+#
+# gazelle:resolve go github.com/cockroachdb/cockroach/pkg/sql/opt/optgen/lang //pkg/sql/opt/optgen/lang
+
 # We exclude a few things from gazelle consideration:
 # - The protobuf C dependency, it's are already bazel-ified, lest we overwrite
 #   those build files
diff --git a/pkg/sql/lexbase/BUILD.bazel b/pkg/sql/lexbase/BUILD.bazel
index 67f173dd8c1f..848c945becb3 100644
--- a/pkg/sql/lexbase/BUILD.bazel
+++ b/pkg/sql/lexbase/BUILD.bazel
@@ -1,10 +1,5 @@
 load("@io_bazel_rules_go//go:def.bzl", "go_library", "go_test")
 
-# TODO(irfansharif): For now we've pinned the auto-generated
-# reserved_keywords.go file. We'll want to eventually teach bazel to generate
-# it within it's sandbox. What this means for now is that Bazel expects the
-# autogenerated file to already have been generated from elsewhere (`make
-# buildshort`).
 go_library(
     name = "lex",
     srcs = [
diff --git a/pkg/sql/opt/optgen/cmd/langgen/BUILD.bazel b/pkg/sql/opt/optgen/cmd/langgen/BUILD.bazel
index 6f9bbe7f0d0c..6cf217e817de 100644
--- a/pkg/sql/opt/optgen/cmd/langgen/BUILD.bazel
+++ b/pkg/sql/opt/optgen/cmd/langgen/BUILD.bazel
@@ -1,5 +1,31 @@
 load("@io_bazel_rules_go//go:def.bzl", "go_binary", "go_library")
 
+# The Optgen language compiler uses itself to generate its AST expressions.
+# This is a form of compiler bootstrapping[1], and needs some manual overrides
+# to fit into how Bazel wants things to be. We define a second go_library
+# target[2], that sources pre-generated og.go files that are already checked
+# into the source tree. These files are used to compile langgen, which is then
+# used to generate newer revisions of those same generated files. All
+# dependants of [3] will need to depend on the og.go files generated in the
+# Bazel sandbox, which is achieved by [4]. Conversely, to instruct
+# gazelle/Bazel to resolve langgen's import of [3] appropriately, we add the
+# resolve directive below.
+#
+# TODO(irfansharif): We'll eventually want to be able to implant the sandbox
+# generated files back into the source tree. This will be necessary for IDEs,
+# but also for a sane workflow for the engineers working on langgen. If they
+# were only using Bazel today, langgen dependent builds would misbehave as we
+# wouldn't be updating the checked-in og.go files used to build langgen itself
+# (assuming any diffs there would result in different code/compilation
+# behavior). See https://github.com/cockroachdb/cockroach/issues/58018.
+#
+# [1]: https://en.wikipedia.org/wiki/Bootstrapping_(compilers)
+# [2]: //pkg/sql/opt/optgen/lang:bootstrap
+# [3]: github.com/cockroachdb/cockroach/pkg/sql/opt/optgen/lang
+# [4]: See the "gazelle:resolve" directive in the top-level BUILD.bazel file
+#
+# gazelle:resolve go github.com/cockroachdb/cockroach/pkg/sql/opt/optgen/lang //pkg/sql/opt/optgen/lang:bootstrap
+
 go_library(
     name = "langgen_lib",
     srcs = [
@@ -10,7 +36,7 @@ go_library(
     importpath = "github.com/cockroachdb/cockroach/pkg/sql/opt/optgen/cmd/langgen",
     visibility = ["//visibility:private"],
     deps = [
-        "//pkg/sql/opt/optgen/lang",
+        "//pkg/sql/opt/optgen/lang:bootstrap",  # keep
         "//vendor/github.com/cockroachdb/errors",
     ],
 )
diff --git a/pkg/sql/opt/optgen/lang/BUILD.bazel b/pkg/sql/opt/optgen/lang/BUILD.bazel
index 882e3c5b5ba8..a3c2404dd7a1 100644
--- a/pkg/sql/opt/optgen/lang/BUILD.bazel
+++ b/pkg/sql/opt/optgen/lang/BUILD.bazel
@@ -7,8 +7,32 @@ go_library(
         "data_type.go",
         "doc.go",
         "expr.go",
-        "expr.og.go",  # keep
-        "operator.og.go",  # keep
+        "operator_string.go",
+        "parser.go",
+        "scanner.go",
+        "token_string.go",
+        ":gen-expr",  # keep
+        ":gen-operator",  # keep
+    ],
+    importpath = "github.com/cockroachdb/cockroach/pkg/sql/opt/optgen/lang",
+    visibility = ["//visibility:public"],
+    deps = ["//vendor/github.com/cockroachdb/errors"],
+)
+
+# Langgen is a bootstrapping compiler. We need to partition the dependencies
+# here to avoid cyclical structures. See the BUILD.bazel file for langgen for
+# more details.
+#
+# keep
+go_library(
+    name = "bootstrap",
+    srcs = [
+        "compiler.go",
+        "data_type.go",
+        "doc.go",
+        "expr.go",
+        "expr.og.go",
+        "operator.og.go",
         "operator_string.go",
         "parser.go",
         "scanner.go",
@@ -33,3 +57,24 @@ go_test(
         "//vendor/github.com/cockroachdb/errors",
     ],
 )
+
+# Define the generator for the expression definitions and functions.
+genrule(
+    name = "gen-expr",
+    srcs = ["lang.opt"],
+    outs = ["expr-gen.og.go"],
+    cmd = """
+      $(location //pkg/sql/opt/optgen/cmd/langgen) -out $@ exprs $(location lang.opt)
+    """,
+    tools = ["//pkg/sql/opt/optgen/cmd/langgen"],
+)
+
+genrule(
+    name = "gen-operator",
+    srcs = ["lang.opt"],
+    outs = ["operator-gen.og.go"],
+    cmd = """
+      $(location //pkg/sql/opt/optgen/cmd/langgen) -out $@ ops $(location lang.opt)
+    """,
+    tools = ["//pkg/sql/opt/optgen/cmd/langgen"],
+)