diff --git a/Cargo.lock b/Cargo.lock
index c5e3621ba0..72da692c47 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -3540,6 +3540,10 @@ dependencies = [
  "roc_types",
 ]
 
+[[package]]
+name = "roc_debug_flags"
+version = "0.1.0"
+
 [[package]]
 name = "roc_docs"
 version = "0.1.0"
@@ -3765,6 +3769,7 @@ dependencies = [
  "roc_can",
  "roc_collections",
  "roc_constrain",
+ "roc_debug_flags",
  "roc_error_macros",
  "roc_module",
  "roc_mono",
@@ -3806,6 +3811,7 @@ dependencies = [
  "roc_builtins",
  "roc_can",
  "roc_collections",
+ "roc_debug_flags",
  "roc_error_macros",
  "roc_exhaustive",
  "roc_module",
@@ -4004,6 +4010,7 @@ version = "0.1.0"
 dependencies = [
  "bumpalo",
  "roc_collections",
+ "roc_debug_flags",
  "roc_error_macros",
  "roc_module",
  "roc_region",
@@ -4017,6 +4024,7 @@ version = "0.1.0"
 dependencies = [
  "bitflags",
  "roc_collections",
+ "roc_debug_flags",
  "roc_error_macros",
  "roc_module",
  "roc_types",
diff --git a/Cargo.toml b/Cargo.toml
index 1e721c0d62..706c467a3a 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -26,6 +26,7 @@ members = [
     "compiler/arena_pool",
     "compiler/test_gen",
     "compiler/roc_target",
+    "compiler/debug_flags",
     "vendor/ena",
     "vendor/inkwell",
     "vendor/pathfinding",
diff --git a/compiler/README.md b/compiler/README.md
index d26c7e862e..d4c93aab03 100644
--- a/compiler/README.md
+++ b/compiler/README.md
@@ -165,23 +165,19 @@ The compiler is invoked from the CLI via `build_file` in cli/src/build.rs
 
 For a more detailed understanding of the compilation phases, see the `Phase`, `BuildTask`, and `Msg` enums in `load/src/file.rs`.
 
-## Debugging intermediate representations
+## Debugging the compiler
 
-### Debugging the typechecker
+Please see the [debug flags](./debug_flags/src/lib.rs) for information on how to
+ask the compiler to emit debug information during various stages of compilation.
 
-Setting the following environment variables:
+There are some goals for more sophisticated debugging tools:
 
-- `ROC_PRINT_UNIFICATIONS` prints all type unifications that are done,
-    before and after the unification.
-- `ROC_PRINT_MISMATCHES` prints all type mismatches hit during unification.
-- `ROC_PRETTY_PRINT_ALIAS_CONTENTS` expands the contents of aliases during
-    pretty-printing of types.
+- A nicer unification debugger, see https://github.com/rtfeldman/roc/issues/2486.
+  Any interest in helping out here is greatly appreciated.
 
-Note that this is only relevant during debug builds. Eventually we should have
-some better debugging tools here, see https://github.com/rtfeldman/roc/issues/2486
-for one.
+### General Tips
 
-### The mono IR
+#### Miscompilations
 
 If you observe a miscomplication, you may first want to check the generated mono
 IR for your code - maybe there was a problem during specialization or layout
@@ -189,13 +185,16 @@ generation. One way to do this is to add a test to `test_mono/src/tests.rs`
 and run the tests with `cargo test -p test_mono`; this will write the mono
 IR to a file.
 
-You may also want to set some or all of the following environment variables:
+#### Typechecking errors
 
-- `PRINT_IR_AFTER_SPECIALIZATION=1` prints the mono IR after function
-    specialization to stdout
-- `PRINT_IR_AFTER_RESET_REUSE=1` prints the mono IR after insertion of
-    reset/reuse isntructions to stdout
-- `PRINT_IR_AFTER_REFCOUNT=1` prints the mono IR after insertion of reference
-    counting instructions to stdout
-- `PRETTY_PRINT_IR_SYMBOLS=1` instructs the pretty printer to dump all the
-    information it knows about the mono IR whenever it is printed
+First, try to minimize your reproduction into a test that fits in
+[`solve_expr`](./solve/tests/solve_expr.rs).
+
+Once you've done this, check out the `ROC_PRINT_UNIFICATIONS` debug flag. It
+will show you where type unification went right and wrong. This is usually
+enough to figure out a fix for the bug.
+
+If that doesn't work and you know your error has something to do with ranks,
+you may want to instrument `deep_copy_var_help` in [solve](./solve/src/solve.rs).
+
+If that doesn't work, chatting on Zulip is always a good strategy.
diff --git a/compiler/debug_flags/Cargo.toml b/compiler/debug_flags/Cargo.toml
new file mode 100644
index 0000000000..8aecfb22ec
--- /dev/null
+++ b/compiler/debug_flags/Cargo.toml
@@ -0,0 +1,6 @@
+[package]
+name = "roc_debug_flags"
+version = "0.1.0"
+edition = "2021"
+
+[dependencies]
diff --git a/compiler/debug_flags/src/lib.rs b/compiler/debug_flags/src/lib.rs
new file mode 100644
index 0000000000..801ab53533
--- /dev/null
+++ b/compiler/debug_flags/src/lib.rs
@@ -0,0 +1,79 @@
+//! Flags for debugging the Roc compiler.
+//!
+//! Lists environment variable flags that can be enabled for verbose debugging features in debug
+//! builds of the compiler.
+//!
+//! For example, I might define the following alias to run cargo with all unifications and
+//! expanded type aliases printed:
+//!
+//! ```bash
+//! alias cargo="\
+//!            ROC_PRINT_UNIFICATIONS=1 \
+//!   ROC_PRETTY_PRINT_ALIAS_CONTENTS=1 \
+//!   cargo"
+//! ```
+//!
+//! More generally, I have the following:
+//!
+//! ```bash
+//! alias cargo="\
+//!     ROC_PRETTY_PRINT_ALIAS_CONTENTS=0 \
+//!              ROC_PRINT_UNIFICATIONS=0 \
+//!                ROC_PRINT_MISMATCHES=0 \
+//!   ROC_PRINT_IR_AFTER_SPECIALIZATION=0 \
+//!      ROC_PRINT_IR_AFTER_RESET_REUSE=0 \
+//!         ROC_PRINT_IR_AFTER_REFCOUNT=0 \
+//!         ROC_PRETTY_PRINT_IR_SYMBOLS=0 \
+//!   cargo"
+//! ```
+//!
+//! Now you can turn debug flags on and off as you like.
+
+#[macro_export]
+macro_rules! dbg_do {
+    ($flag:path, $expr:expr) => {
+        #[cfg(debug_assertions)]
+        {
+            if std::env::var($flag).unwrap_or("0".to_string()) != "0" {
+                $expr
+            }
+        }
+    };
+}
+
+macro_rules! flags {
+    ($($(#[doc = $doc:expr])+ $flag:ident)*) => {$(
+        $(#[doc = $doc])+
+        pub static $flag: &str = stringify!($flag);
+    )*};
+}
+
+flags! {
+    // ===Types===
+
+    /// Expands the contents of aliases during pretty-printing of types.
+    ROC_PRETTY_PRINT_ALIAS_CONTENTS
+
+    // ===Solve===
+
+    /// Prints type unifications, before and after they happen.
+    ROC_PRINT_UNIFICATIONS
+
+    /// Prints all type mismatches hit during type unification.
+    ROC_PRINT_MISMATCHES
+
+    // ===Mono===
+
+    /// Writes the mono IR to stderr after function specialization
+    ROC_PRINT_IR_AFTER_SPECIALIZATION
+
+    /// Writes the mono IR to stderr after insertion of reset/reuse instructions
+    ROC_PRINT_IR_AFTER_RESET_REUSE
+
+    /// Writes the mono IR to stderr after insertion of refcount instructions
+    ROC_PRINT_IR_AFTER_REFCOUNT
+
+    /// Instructs the mono IR pretty printer to dump pretty symbols and verbose
+    /// layout information
+    ROC_PRETTY_PRINT_IR_SYMBOLS
+}
diff --git a/compiler/load_internal/Cargo.toml b/compiler/load_internal/Cargo.toml
index 28641d1c1b..df3ffe4ffb 100644
--- a/compiler/load_internal/Cargo.toml
+++ b/compiler/load_internal/Cargo.toml
@@ -21,6 +21,7 @@ roc_solve = { path = "../solve" }
 roc_mono = { path = "../mono" }
 roc_target = { path = "../roc_target" }
 roc_reporting = { path = "../../reporting" }
+roc_debug_flags = { path = "../debug_flags" }
 morphic_lib = { path = "../../vendor/morphic_lib" }
 ven_pretty = { path = "../../vendor/pretty" }
 bumpalo = { version = "3.8.0", features = ["collections"] }
@@ -33,4 +34,4 @@ tempfile = "3.2.0"
 pretty_assertions = "1.0.0"
 maplit = "1.0.2"
 indoc = "1.0.3"
-roc_test_utils = { path = "../../test_utils" }
\ No newline at end of file
+roc_test_utils = { path = "../../test_utils" }
diff --git a/compiler/load_internal/src/file.rs b/compiler/load_internal/src/file.rs
index 7fa6bf8292..27884c80fe 100644
--- a/compiler/load_internal/src/file.rs
+++ b/compiler/load_internal/src/file.rs
@@ -15,6 +15,10 @@ use roc_constrain::module::{
     constrain_builtin_imports, constrain_module, ExposedByModule, ExposedForModule,
     ExposedModuleTypes,
 };
+use roc_debug_flags::{
+    dbg_do, ROC_PRINT_IR_AFTER_REFCOUNT, ROC_PRINT_IR_AFTER_RESET_REUSE,
+    ROC_PRINT_IR_AFTER_SPECIALIZATION,
+};
 use roc_error_macros::internal_error;
 use roc_module::ident::{Ident, ModuleName, QualifiedModuleName};
 use roc_module::symbol::{
@@ -1627,21 +1631,20 @@ fn start_tasks<'a>(
     Ok(())
 }
 
-#[cfg(debug_assertions)]
-fn debug_print_ir(state: &State, flag: &str) {
-    if env::var(flag) != Ok("1".into()) {
-        return;
-    }
+macro_rules! debug_print_ir {
+    ($state:expr, $flag:path) => {
+        dbg_do!($flag, {
+            let procs_string = $state
+                .procedures
+                .values()
+                .map(|proc| proc.to_pretty(200))
+                .collect::<Vec<_>>();
 
-    let procs_string = state
-        .procedures
-        .values()
-        .map(|proc| proc.to_pretty(200))
-        .collect::<Vec<_>>();
+            let result = procs_string.join("\n");
 
-    let result = procs_string.join("\n");
-
-    println!("{}", result);
+            eprintln!("{}", result);
+        })
+    };
 }
 
 /// Report modules that are imported, but from which nothing is used
@@ -2181,8 +2184,7 @@ fn update<'a>(
                 && state.dependencies.solved_all()
                 && state.goal_phase == Phase::MakeSpecializations
             {
-                #[cfg(debug_assertions)]
-                debug_print_ir(&state, "PRINT_IR_AFTER_SPECIALIZATION");
+                debug_print_ir!(state, ROC_PRINT_IR_AFTER_SPECIALIZATION);
 
                 Proc::insert_reset_reuse_operations(
                     arena,
@@ -2192,13 +2194,11 @@ fn update<'a>(
                     &mut state.procedures,
                 );
 
-                #[cfg(debug_assertions)]
-                debug_print_ir(&state, "PRINT_IR_AFTER_RESET_REUSE");
+                debug_print_ir!(state, ROC_PRINT_IR_AFTER_RESET_REUSE);
 
                 Proc::insert_refcount_operations(arena, &mut state.procedures);
 
-                #[cfg(debug_assertions)]
-                debug_print_ir(&state, "PRINT_IR_AFTER_REFCOUNT");
+                debug_print_ir!(state, ROC_PRINT_IR_AFTER_REFCOUNT);
 
                 // This is not safe with the new non-recursive RC updates that we do for tag unions
                 //
diff --git a/compiler/mono/Cargo.toml b/compiler/mono/Cargo.toml
index d47714ebdd..79b1ea060c 100644
--- a/compiler/mono/Cargo.toml
+++ b/compiler/mono/Cargo.toml
@@ -19,6 +19,7 @@ roc_problem = { path = "../problem" }
 roc_builtins = { path = "../builtins" }
 roc_target = { path = "../roc_target" }
 roc_error_macros = {path="../../error_macros"}
+roc_debug_flags = {path="../debug_flags"}
 ven_pretty = { path = "../../vendor/pretty" }
 morphic_lib = { path = "../../vendor/morphic_lib" }
 bumpalo = { version = "3.8.0", features = ["collections"] }
diff --git a/compiler/mono/src/ir.rs b/compiler/mono/src/ir.rs
index 1b0875c14a..790eaef5ce 100644
--- a/compiler/mono/src/ir.rs
+++ b/compiler/mono/src/ir.rs
@@ -10,6 +10,7 @@ use roc_builtins::bitcode::{FloatWidth, IntWidth};
 use roc_can::abilities::AbilitiesStore;
 use roc_can::expr::{AnnotatedMark, ClosureData, IntValue};
 use roc_collections::all::{default_hasher, BumpMap, BumpMapDefault, MutMap};
+use roc_debug_flags::{dbg_do, ROC_PRETTY_PRINT_IR_SYMBOLS};
 use roc_exhaustive::{Ctor, CtorName, Guard, RenderAs, TagId};
 use roc_module::ident::{ForeignSymbol, Lowercase, TagName};
 use roc_module::low_level::LowLevel;
@@ -25,11 +26,11 @@ use roc_types::subs::{
 use std::collections::HashMap;
 use ven_pretty::{BoxAllocator, DocAllocator, DocBuilder};
 
+#[inline(always)]
 pub fn pretty_print_ir_symbols() -> bool {
-    #[cfg(debug_assertions)]
-    if std::env::var("PRETTY_PRINT_IR_SYMBOLS") == Ok("1".into()) {
+    dbg_do!(ROC_PRETTY_PRINT_IR_SYMBOLS, {
         return true;
-    }
+    });
     false
 }
 
diff --git a/compiler/types/Cargo.toml b/compiler/types/Cargo.toml
index 550cb5f333..e00c368701 100644
--- a/compiler/types/Cargo.toml
+++ b/compiler/types/Cargo.toml
@@ -10,6 +10,7 @@ roc_collections = { path = "../collections" }
 roc_region = { path = "../region" }
 roc_module = { path = "../module" }
 roc_error_macros = {path="../../error_macros"}
+roc_debug_flags = {path="../debug_flags"}
 ven_ena = { path = "../../vendor/ena" }
 bumpalo = { version = "3.8.0", features = ["collections"] }
 static_assertions = "1.1.0"
diff --git a/compiler/types/src/pretty_print.rs b/compiler/types/src/pretty_print.rs
index 917e4a33e0..b266edddb8 100644
--- a/compiler/types/src/pretty_print.rs
+++ b/compiler/types/src/pretty_print.rs
@@ -449,15 +449,12 @@ fn write_content<'a>(
                         );
                     }
 
-                    // useful for debugging
-                    if cfg!(debug_assertions)
-                        && std::env::var("ROC_PRETTY_PRINT_ALIAS_CONTENTS").is_ok()
-                    {
+                    roc_debug_flags::dbg_do!(roc_debug_flags::ROC_PRETTY_PRINT_ALIAS_CONTENTS, {
                         buf.push_str("[[ but really ");
                         let content = subs.get_content_without_compacting(*_actual);
                         write_content(env, ctx, content, subs, buf, parens);
                         buf.push_str("]]");
-                    }
+                    });
                 }),
             }
         }
diff --git a/compiler/unify/Cargo.toml b/compiler/unify/Cargo.toml
index d8622ed928..e92e2aa3e3 100644
--- a/compiler/unify/Cargo.toml
+++ b/compiler/unify/Cargo.toml
@@ -19,3 +19,6 @@ path = "../module"
 
 [dependencies.roc_types]
 path = "../types"
+
+[dependencies.roc_debug_flags]
+path = "../debug_flags"
diff --git a/compiler/unify/src/unify.rs b/compiler/unify/src/unify.rs
index f5c224bc09..9a5ca9a28a 100644
--- a/compiler/unify/src/unify.rs
+++ b/compiler/unify/src/unify.rs
@@ -1,4 +1,5 @@
 use bitflags::bitflags;
+use roc_debug_flags::{dbg_do, ROC_PRINT_MISMATCHES, ROC_PRINT_UNIFICATIONS};
 use roc_error_macros::internal_error;
 use roc_module::ident::{Lowercase, TagName};
 use roc_module::symbol::Symbol;
@@ -11,14 +12,14 @@ use roc_types::types::{AliasKind, DoesNotImplementAbility, ErrorType, Mismatch,
 
 macro_rules! mismatch {
     () => {{
-        if cfg!(debug_assertions) && std::env::var("ROC_PRINT_MISMATCHES").is_ok() {
-            println!(
+        dbg_do!(ROC_PRINT_MISMATCHES, {
+            eprintln!(
                 "Mismatch in {} Line {} Column {}",
                 file!(),
                 line!(),
                 column!()
             );
-        }
+        })
 
         Outcome {
             mismatches: vec![Mismatch::TypeMismatch],
@@ -26,17 +27,16 @@ macro_rules! mismatch {
         }
     }};
     ($msg:expr) => {{
-        if cfg!(debug_assertions) && std::env::var("ROC_PRINT_MISMATCHES").is_ok() {
-            println!(
+        dbg_do!(ROC_PRINT_MISMATCHES, {
+            eprintln!(
                 "Mismatch in {} Line {} Column {}",
                 file!(),
                 line!(),
                 column!()
             );
-            println!($msg);
-            println!("");
-        }
-
+            eprintln!($msg);
+            eprintln!("");
+        });
 
         Outcome {
             mismatches: vec![Mismatch::TypeMismatch],
@@ -47,16 +47,16 @@ macro_rules! mismatch {
         mismatch!($msg)
     }};
     ($msg:expr, $($arg:tt)*) => {{
-        if cfg!(debug_assertions) && std::env::var("ROC_PRINT_MISMATCHES").is_ok() {
-            println!(
+        dbg_do!(ROC_PRINT_MISMATCHES, {
+            eprintln!(
                 "Mismatch in {} Line {} Column {}",
                 file!(),
                 line!(),
                 column!()
             );
-            println!($msg, $($arg)*);
-            println!("");
-        }
+            eprintln!($msg, $($arg)*);
+            eprintln!("");
+        });
 
         Outcome {
             mismatches: vec![Mismatch::TypeMismatch],
@@ -64,16 +64,16 @@ macro_rules! mismatch {
         }
     }};
     (%not_able, $var:expr, $ability:expr, $msg:expr, $($arg:tt)*) => {{
-        if cfg!(debug_assertions) && std::env::var("ROC_PRINT_MISMATCHES").is_ok() {
-            println!(
+        dbg_do!(ROC_PRINT_MISMATCHES, {
+            eprintln!(
                 "Mismatch in {} Line {} Column {}",
                 file!(),
                 line!(),
                 column!()
             );
-            println!($msg, $($arg)*);
-            println!("");
-        }
+            eprintln!($msg, $($arg)*);
+            eprintln!("");
+        });
 
         Outcome {
             mismatches: vec![Mismatch::TypeMismatch, Mismatch::DoesNotImplementAbiity($var, $ability)],
@@ -298,7 +298,7 @@ fn debug_print_unified_types(subs: &mut Subs, ctx: &Context, opt_outcome: Option
 
     static mut UNIFICATION_DEPTH: usize = 0;
 
-    if std::env::var("ROC_PRINT_UNIFICATIONS").is_ok() {
+    dbg_do!(ROC_PRINT_UNIFICATIONS, {
         let prefix = match opt_outcome {
             None => "❔",
             Some(outcome) if outcome.mismatches.is_empty() => "✅",
@@ -340,7 +340,7 @@ fn debug_print_unified_types(subs: &mut Subs, ctx: &Context, opt_outcome: Option
         );
 
         unsafe { UNIFICATION_DEPTH = new_depth };
-    }
+    })
 }
 
 fn unify_context(subs: &mut Subs, pool: &mut Pool, ctx: Context) -> Outcome {