diff --git a/.github/workflows/llvm.yml b/.github/workflows/llvm.yml
index dab5b9bb74cd..796b26a66c08 100644
--- a/.github/workflows/llvm.yml
+++ b/.github/workflows/llvm.yml
@@ -17,17 +17,19 @@ jobs:
       matrix:
         include:
           - llvm_version: "13.0.0"
-            llvm_ubuntu_version: "20.04"
+            llvm_filename: "clang+llvm-13.0.0-x86_64-linux-gnu-ubuntu-20.04.tar.xz"
           - llvm_version: "14.0.0"
-            llvm_ubuntu_version: "18.04"
+            llvm_filename: "clang+llvm-14.0.0-x86_64-linux-gnu-ubuntu-18.04.tar.xz"
           - llvm_version: "15.0.6"
-            llvm_ubuntu_version: "18.04"
+            llvm_filename: "clang+llvm-15.0.6-x86_64-linux-gnu-ubuntu-18.04.tar.xz"
           - llvm_version: "16.0.3"
-            llvm_ubuntu_version: "22.04"
+            llvm_filename: "clang+llvm-16.0.3-x86_64-linux-gnu-ubuntu-22.04.tar.xz"
           - llvm_version: "17.0.6"
-            llvm_ubuntu_version: "22.04"
+            llvm_filename: "clang+llvm-17.0.6-x86_64-linux-gnu-ubuntu-22.04.tar.xz"
           - llvm_version: "18.1.4"
-            llvm_ubuntu_version: "18.04"
+            llvm_filename: "clang+llvm-18.1.4-x86_64-linux-gnu-ubuntu-18.04.tar.xz"
+          - llvm_version: "19.1.0"
+            llvm_filename: "LLVM-19.1.0-Linux-X64.tar.xz"
     name: "LLVM ${{ matrix.llvm_version }}"
     steps:
       - name: Checkout Crystal source
@@ -44,7 +46,7 @@ jobs:
       - name: Install LLVM ${{ matrix.llvm_version }}
         run: |
           mkdir -p llvm
-          curl -L "https://github.com/llvm/llvm-project/releases/download/llvmorg-${{ matrix.llvm_version }}/clang+llvm-${{ matrix.llvm_version }}-x86_64-linux-gnu-ubuntu-${{ matrix.llvm_ubuntu_version }}.tar.xz" > llvm.tar.xz
+          curl -L "https://github.com/llvm/llvm-project/releases/download/llvmorg-${{ matrix.llvm_version }}/${{ matrix.llvm_filename }}" > llvm.tar.xz
           tar x --xz -C llvm --strip-components=1 -f llvm.tar.xz
         if: steps.cache-llvm.outputs.cache-hit != 'true'
 
diff --git a/spec/compiler/codegen/debug_spec.cr b/spec/compiler/codegen/debug_spec.cr
index 4a57056fc7a3..0032fcb64b4c 100644
--- a/spec/compiler/codegen/debug_spec.cr
+++ b/spec/compiler/codegen/debug_spec.cr
@@ -160,8 +160,6 @@ describe "Code gen: debug" do
 
   it "has debug info in closure inside if (#5593)" do
     codegen(%(
-      require "prelude"
-
       def foo
         if true && true
           yield 1
diff --git a/src/compiler/crystal/codegen/debug.cr b/src/compiler/crystal/codegen/debug.cr
index 72555d074bb0..9a03420ba203 100644
--- a/src/compiler/crystal/codegen/debug.cr
+++ b/src/compiler/crystal/codegen/debug.cr
@@ -367,6 +367,16 @@ module Crystal
       old_debug_location = @current_debug_location
       set_current_debug_location location
       if builder.current_debug_location != llvm_nil && (ptr = alloca)
+        # FIXME: When debug records are used instead of debug intrinsics, it
+        # seems inserting them into an empty BasicBlock will instead place them
+        # in a totally different (next?) function where the variable doesn't
+        # exist, leading to a "function-local metadata used in wrong function"
+        # validation error. This might happen when e.g. all variables inside a
+        # block are closured. Ideally every debug record should immediately
+        # follow the variable it declares.
+        {% unless LibLLVM::IS_LT_190 %}
+          call(do_nothing_fun) if block.instructions.empty?
+        {% end %}
         di_builder.insert_declare_at_end(ptr, var, expr, builder.current_debug_location_metadata, block)
         set_current_debug_location old_debug_location
         true
@@ -376,6 +386,12 @@ module Crystal
       end
     end
 
+    private def do_nothing_fun
+      fetch_typed_fun(@llvm_mod, "llvm.donothing") do
+        LLVM::Type.function([] of LLVM::Type, @llvm_context.void)
+      end
+    end
+
     # Emit debug info for toplevel variables. Used for the main module and all
     # required files.
     def emit_vars_debug_info(vars)
diff --git a/src/intrinsics.cr b/src/intrinsics.cr
index 7cdc462ce543..dc83ab91c884 100644
--- a/src/intrinsics.cr
+++ b/src/intrinsics.cr
@@ -163,8 +163,13 @@ lib LibIntrinsics
   {% if flag?(:interpreted) %} @[Primitive(:interpreter_intrinsics_fshr128)] {% end %}
   fun fshr128 = "llvm.fshr.i128"(a : UInt128, b : UInt128, count : UInt128) : UInt128
 
-  fun va_start = "llvm.va_start"(ap : Void*)
-  fun va_end = "llvm.va_end"(ap : Void*)
+  {% if compare_versions(Crystal::LLVM_VERSION, "19.1.0") < 0 %}
+    fun va_start = "llvm.va_start"(ap : Void*)
+    fun va_end = "llvm.va_end"(ap : Void*)
+  {% else %}
+    fun va_start = "llvm.va_start.p0"(ap : Void*)
+    fun va_end = "llvm.va_end.p0"(ap : Void*)
+  {% end %}
 
   {% if flag?(:i386) || flag?(:x86_64) %}
     {% if flag?(:interpreted) %} @[Primitive(:interpreter_intrinsics_pause)] {% end %}
diff --git a/src/llvm/context.cr b/src/llvm/context.cr
index 987e8f13ba6b..84c96610a96f 100644
--- a/src/llvm/context.cr
+++ b/src/llvm/context.cr
@@ -108,7 +108,11 @@ class LLVM::Context
   end
 
   def const_string(string : String) : Value
-    Value.new LibLLVM.const_string_in_context(self, string, string.bytesize, 0)
+    {% if LibLLVM::IS_LT_190 %}
+      Value.new LibLLVM.const_string_in_context(self, string, string.bytesize, 0)
+    {% else %}
+      Value.new LibLLVM.const_string_in_context2(self, string, string.bytesize, 0)
+    {% end %}
   end
 
   def const_struct(values : Array(LLVM::Value), packed = false) : Value
diff --git a/src/llvm/di_builder.cr b/src/llvm/di_builder.cr
index 37be65ef8cf8..7a06a7041349 100644
--- a/src/llvm/di_builder.cr
+++ b/src/llvm/di_builder.cr
@@ -96,7 +96,11 @@ struct LLVM::DIBuilder
   end
 
   def insert_declare_at_end(storage, var_info, expr, dl : LibLLVM::MetadataRef, block)
-    LibLLVM.di_builder_insert_declare_at_end(self, storage, var_info, expr, dl, block)
+    {% if LibLLVM::IS_LT_190 %}
+      LibLLVM.di_builder_insert_declare_at_end(self, storage, var_info, expr, dl, block)
+    {% else %}
+      LibLLVM.di_builder_insert_declare_record_at_end(self, storage, var_info, expr, dl, block)
+    {% end %}
   end
 
   def get_or_create_array(elements : Array(LibLLVM::MetadataRef))
diff --git a/src/llvm/ext/llvm-versions.txt b/src/llvm/ext/llvm-versions.txt
index 92ae5ecbaa5a..6f4d3d4816d0 100644
--- a/src/llvm/ext/llvm-versions.txt
+++ b/src/llvm/ext/llvm-versions.txt
@@ -1 +1 @@
-18.1 17.0 16.0 15.0 14.0 13.0 12.0 11.1 11.0 10.0 9.0 8.0
+19.1 18.1 17.0 16.0 15.0 14.0 13.0 12.0 11.1 11.0 10.0 9.0 8.0
diff --git a/src/llvm/lib_llvm.cr b/src/llvm/lib_llvm.cr
index 976cedc90df5..4c7ed49e7900 100644
--- a/src/llvm/lib_llvm.cr
+++ b/src/llvm/lib_llvm.cr
@@ -65,6 +65,7 @@
     IS_LT_160 = {{compare_versions(LibLLVM::VERSION, "16.0.0") < 0}}
     IS_LT_170 = {{compare_versions(LibLLVM::VERSION, "17.0.0") < 0}}
     IS_LT_180 = {{compare_versions(LibLLVM::VERSION, "18.0.0") < 0}}
+    IS_LT_190 = {{compare_versions(LibLLVM::VERSION, "19.0.0") < 0}}
   end
 {% end %}
 
diff --git a/src/llvm/lib_llvm/core.cr b/src/llvm/lib_llvm/core.cr
index ff3327a3f78d..1796bd00a0ee 100644
--- a/src/llvm/lib_llvm/core.cr
+++ b/src/llvm/lib_llvm/core.cr
@@ -116,7 +116,11 @@ lib LibLLVM
   fun const_int_get_zext_value = LLVMConstIntGetZExtValue(constant_val : ValueRef) : ULongLong
   fun const_int_get_sext_value = LLVMConstIntGetSExtValue(constant_val : ValueRef) : LongLong
 
-  fun const_string_in_context = LLVMConstStringInContext(c : ContextRef, str : Char*, length : UInt, dont_null_terminate : Bool) : ValueRef
+  {% if LibLLVM::IS_LT_190 %}
+    fun const_string_in_context = LLVMConstStringInContext(c : ContextRef, str : Char*, length : UInt, dont_null_terminate : Bool) : ValueRef
+  {% else %}
+    fun const_string_in_context2 = LLVMConstStringInContext2(c : ContextRef, str : Char*, length : SizeT, dont_null_terminate : Bool) : ValueRef
+  {% end %}
   fun const_struct_in_context = LLVMConstStructInContext(c : ContextRef, constant_vals : ValueRef*, count : UInt, packed : Bool) : ValueRef
   fun const_array = LLVMConstArray(element_ty : TypeRef, constant_vals : ValueRef*, length : UInt) : ValueRef
 
diff --git a/src/llvm/lib_llvm/debug_info.cr b/src/llvm/lib_llvm/debug_info.cr
index e97e8c71a177..e6155b317eb5 100644
--- a/src/llvm/lib_llvm/debug_info.cr
+++ b/src/llvm/lib_llvm/debug_info.cr
@@ -111,10 +111,17 @@ lib LibLLVM
 
   fun metadata_replace_all_uses_with = LLVMMetadataReplaceAllUsesWith(target_metadata : MetadataRef, replacement : MetadataRef)
 
-  fun di_builder_insert_declare_at_end = LLVMDIBuilderInsertDeclareAtEnd(
-    builder : DIBuilderRef, storage : ValueRef, var_info : MetadataRef,
-    expr : MetadataRef, debug_loc : MetadataRef, block : BasicBlockRef
-  ) : ValueRef
+  {% if LibLLVM::IS_LT_190 %}
+    fun di_builder_insert_declare_at_end = LLVMDIBuilderInsertDeclareAtEnd(
+      builder : DIBuilderRef, storage : ValueRef, var_info : MetadataRef,
+      expr : MetadataRef, debug_loc : MetadataRef, block : BasicBlockRef
+    ) : ValueRef
+  {% else %}
+    fun di_builder_insert_declare_record_at_end = LLVMDIBuilderInsertDeclareRecordAtEnd(
+      builder : DIBuilderRef, storage : ValueRef, var_info : MetadataRef,
+      expr : MetadataRef, debug_loc : MetadataRef, block : BasicBlockRef
+    ) : DbgRecordRef
+  {% end %}
 
   fun di_builder_create_auto_variable = LLVMDIBuilderCreateAutoVariable(
     builder : DIBuilderRef, scope : MetadataRef, name : Char*, name_len : SizeT, file : MetadataRef,
diff --git a/src/llvm/lib_llvm/types.cr b/src/llvm/lib_llvm/types.cr
index a1b374f30219..532078394794 100644
--- a/src/llvm/lib_llvm/types.cr
+++ b/src/llvm/lib_llvm/types.cr
@@ -17,4 +17,5 @@ lib LibLLVM
   {% end %}
   type OperandBundleRef = Void*
   type AttributeRef = Void*
+  type DbgRecordRef = Void*
 end