diff --git a/.github/workflows/ci.generate.ts b/.github/workflows/ci.generate.ts
index f24034d4941983..63772f4f8150c4 100755
--- a/.github/workflows/ci.generate.ts
+++ b/.github/workflows/ci.generate.ts
@@ -720,6 +720,33 @@ const ci = {
             "df -h",
           ].join("\n"),
         },
+        {
+          name: "Strip and separate debug info (linux)",
+          if: [
+            "matrix.os == 'linux' &&",
+            "(matrix.job == 'test' || matrix.job == 'bench') &&",
+            "matrix.profile == 'release' && (matrix.use_sysroot ||",
+            "github.repository == 'denoland/deno')",
+          ].join("\n"),
+          run: [
+            "objcopy --only-keep-debug target/release/deno target/release/deno.debug",
+            "objcopy --add-gnu-debuglink target/release/deno.debug target/release/deno",
+            "strip -s target/release/deno",
+          ],
+        },
+        {
+          name: "Strip and separate debug info (mac)",
+          if: [
+            "matrix.os == 'macos' &&",
+            "(matrix.job == 'test' || matrix.job == 'bench') &&",
+            "matrix.profile == 'release' && (matrix.use_sysroot ||",
+            "github.repository == 'denoland/deno')",
+          ].join("\n"),
+          run: [
+            "dsymutil target/release/deno",
+            "strip target/release/deno",
+          ],
+        },
         {
           // Run a minimal check to ensure that binary is not corrupted, regardless
           // of our build mode
@@ -766,6 +793,8 @@ const ci = {
             "cd target/release",
             "zip -r deno-${{ matrix.arch }}-unknown-linux-gnu.zip deno",
             "shasum -a 256 deno-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
+            "zip -r deno-debuginfo-${{ matrix.arch}}-unknown-linux-gnu.zip deno.debug",
+            "shasum -a 256 deno-debuginfo-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-debuginfo-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
             "strip denort",
             "zip -r denort-${{ matrix.arch }}-unknown-linux-gnu.zip denort",
             "shasum -a 256 denort-${{ matrix.arch }}-unknown-linux-gnu.zip > denort-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
@@ -794,6 +823,8 @@ const ci = {
             "cd target/release",
             "zip -r deno-${{ matrix.arch }}-apple-darwin.zip deno",
             "shasum -a 256 deno-${{ matrix.arch }}-apple-darwin.zip > deno-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
+            "zip -r deno-debuginfo-${{ matrix.arch }}-apple-darwin.zip deno.dSYM",
+            "shasum -a 256 deno-debuginfo-${{ matrix.arch }}-apple-darwin.zip > deno-debuginfo-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
             "strip denort",
             "zip -r denort-${{ matrix.arch }}-apple-darwin.zip denort",
             "shasum -a 256 denort-${{ matrix.arch }}-apple-darwin.zip > denort-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
@@ -812,6 +843,8 @@ const ci = {
           run: [
             "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.exe -DestinationPath target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip",
             "Get-FileHash target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
+            "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.pdb -DestinationPath target/release/deno-debuginfo-${{ matrix.arch }}-pc-windows-msvc.zip",
+            "Get-FileHash target/release/deno-debuginfo-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-debuginfo-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
             "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/denort.exe -DestinationPath target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip",
             "Get-FileHash target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
           ].join("\n"),
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index efbf6f61664425..687ba73daad056 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -417,6 +417,25 @@ jobs:
           df -h
           cargo build --release --locked --all-targets
           df -h
+      - name: Strip and separate debug info (linux)
+        if: |-
+          !(matrix.skip) && (matrix.os == 'linux' &&
+          (matrix.job == 'test' || matrix.job == 'bench') &&
+          matrix.profile == 'release' && (matrix.use_sysroot ||
+          github.repository == 'denoland/deno'))
+        run:
+          - objcopy --only-keep-debug target/release/deno target/release/deno.debug
+          - objcopy --add-gnu-debuglink target/release/deno.debug target/release/deno
+          - strip -s target/release/deno
+      - name: Strip and separate debug info (mac)
+        if: |-
+          !(matrix.skip) && (matrix.os == 'macos' &&
+          (matrix.job == 'test' || matrix.job == 'bench') &&
+          matrix.profile == 'release' && (matrix.use_sysroot ||
+          github.repository == 'denoland/deno'))
+        run:
+          - dsymutil target/release/deno
+          - strip target/release/deno
       - name: Check deno binary
         if: '!(matrix.skip) && (matrix.job == ''test'')'
         run: 'target/${{ matrix.profile }}/deno eval "console.log(1+2)" | grep 3'
@@ -446,6 +465,8 @@ jobs:
           cd target/release
           zip -r deno-${{ matrix.arch }}-unknown-linux-gnu.zip deno
           shasum -a 256 deno-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
+          zip -r deno-debuginfo-${{ matrix.arch}}-unknown-linux-gnu.zip deno.debug
+          shasum -a 256 deno-debuginfo-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-debuginfo-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
           strip denort
           zip -r denort-${{ matrix.arch }}-unknown-linux-gnu.zip denort
           shasum -a 256 denort-${{ matrix.arch }}-unknown-linux-gnu.zip > denort-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
@@ -465,6 +486,8 @@ jobs:
           cd target/release
           zip -r deno-${{ matrix.arch }}-apple-darwin.zip deno
           shasum -a 256 deno-${{ matrix.arch }}-apple-darwin.zip > deno-${{ matrix.arch }}-apple-darwin.zip.sha256sum
+          zip -r deno-debuginfo-${{ matrix.arch }}-apple-darwin.zip deno.dSYM
+          shasum -a 256 deno-debuginfo-${{ matrix.arch }}-apple-darwin.zip > deno-debuginfo-${{ matrix.arch }}-apple-darwin.zip.sha256sum
           strip denort
           zip -r denort-${{ matrix.arch }}-apple-darwin.zip denort
           shasum -a 256 denort-${{ matrix.arch }}-apple-darwin.zip > denort-${{ matrix.arch }}-apple-darwin.zip.sha256sum
@@ -478,6 +501,8 @@ jobs:
         run: |-
           Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.exe -DestinationPath target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip
           Get-FileHash target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
+          Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.pdb -DestinationPath target/release/deno-debuginfo-${{ matrix.arch }}-pc-windows-msvc.zip
+          Get-FileHash target/release/deno-debuginfo-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-debuginfo-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
           Compress-Archive -CompressionLevel Optimal -Force -Path target/release/denort.exe -DestinationPath target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip
           Get-FileHash target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
       - name: Upload canary to dl.deno.land
diff --git a/Cargo.lock b/Cargo.lock
index 2c8f327b5bff73..c8c4de339c8240 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -511,7 +511,7 @@ version = "0.70.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f49d8fed880d473ea71efb9bf597651e77201bdd4893efe54c9e5d65ae04ce6f"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "cexpr",
  "clang-sys",
  "itertools 0.13.0",
@@ -548,9 +548,9 @@ checksum = "bef38d45163c2f1dde094a7dfd33ccf595c92905c8f8f4fdc18d06fb1037718a"
 
 [[package]]
 name = "bitflags"
-version = "2.6.0"
+version = "2.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b048fb63fd8b5923fc5aa7b340d8e156aec7ec02f0c78fa8a6ddc2613f6f71de"
+checksum = "8f68f53c83ab957f72c32642f3868eec03eb974d1fb82e453128456482613d36"
 dependencies = [
  "serde",
 ]
@@ -726,13 +726,13 @@ dependencies = [
 
 [[package]]
 name = "cc"
-version = "1.0.106"
+version = "1.2.10"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "066fce287b1d4eafef758e89e09d724a24808a9196fe9756b8ca90e86d0719a2"
+checksum = "13208fcbb66eaeffe09b99fffbe1af420f00a7b35aa99ad683dfc1aa76145229"
 dependencies = [
  "jobserver",
  "libc",
- "once_cell",
+ "shlex",
 ]
 
 [[package]]
@@ -1170,7 +1170,7 @@ version = "0.20.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b28bfe653d79bd16c77f659305b195b82bb5ce0c0eb2a4846b82ddbd77586813"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "libloading 0.8.5",
  "winapi",
 ]
@@ -1364,6 +1364,7 @@ dependencies = [
  "tracing",
  "twox-hash",
  "typed-arena",
+ "ureq",
  "uuid",
  "walkdir",
  "which",
@@ -3777,7 +3778,7 @@ version = "0.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "fbcd2dba93594b227a1f57ee09b8b9da8892c34d55aa332e034a228d0fe6a171"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "gpu-alloc-types",
 ]
 
@@ -3787,7 +3788,7 @@ version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "98ff03b468aa837d70984d55f5d3f846f6ec31fe34bbb97c4f85219caeee1ca4"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
 ]
 
 [[package]]
@@ -3796,7 +3797,7 @@ version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "9c08c1f623a8d0b722b8b99f821eb0ba672a1618f0d3b16ddbee1cedd2dd8557"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "gpu-descriptor-types",
  "hashbrown 0.14.5",
 ]
@@ -3807,7 +3808,7 @@ version = "0.2.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "fdf242682df893b86f33a73828fb09ca4b2d3bb6cc95249707fc684d27484b91"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
 ]
 
 [[package]]
@@ -4849,7 +4850,7 @@ version = "0.1.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "c0ff37bd590ca25063e35af745c343cb7a0271906fb7b37e4813e8f79f00268d"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "libc",
 ]
 
@@ -5074,7 +5075,7 @@ version = "0.28.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5637e166ea14be6063a3f8ba5ccb9a4159df7d8f6d61c02fc3d480b1f90dcfcb"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "block",
  "core-graphics-types",
  "foreign-types",
@@ -5162,7 +5163,7 @@ checksum = "e536ae46fcab0876853bd4a632ede5df4b1c2527a58f6c5a4150fe86be858231"
 dependencies = [
  "arrayvec",
  "bit-set",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "codespan-reporting",
  "hexf-parse",
  "indexmap 2.3.0",
@@ -5241,7 +5242,7 @@ version = "0.27.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "2eb04e9c688eff1c89d72b407f168cf79bb9e867a9d3323ed6c01519eb9cc053"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "cfg-if",
  "libc",
 ]
@@ -5295,7 +5296,7 @@ version = "6.1.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6205bd8bb1e454ad2e27422015fb5e4f2bcc7e08fa8f27058670d208324a4d2d"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "crossbeam-channel",
  "filetime",
  "fsevent-sys",
@@ -6142,7 +6143,7 @@ version = "0.11.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "cb4e75767fbc9d92b90e4d0c011f61358cde9513b31ef07ea3631b15ffc3b4fd"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "memchr",
  "unicase",
 ]
@@ -6530,7 +6531,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b91f7eff05f748767f183df4320a63d6936e9c6107d97c9e6bdd9784f4289c94"
 dependencies = [
  "base64 0.21.7",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "serde",
  "serde_derive",
 ]
@@ -6599,7 +6600,7 @@ version = "0.32.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1cdbe9230a57259b37f7257d0aff38b8c9dbda3513edba2105e59b130189d82f"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "fallible-iterator",
  "fallible-streaming-iterator",
  "hashlink",
@@ -6658,7 +6659,7 @@ version = "0.38.32"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "65e04861e65f21776e67888bfbea442b3642beaa0138fdb1dd7a84a52dffdb89"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "errno",
  "libc",
  "linux-raw-sys",
@@ -6667,9 +6668,9 @@ dependencies = [
 
 [[package]]
 name = "rustls"
-version = "0.23.11"
+version = "0.23.21"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4828ea528154ae444e5a642dbb7d5623354030dc9822b83fd9bb79683c7399d0"
+checksum = "8f287924602bf649d949c63dc8ac8b235fa5387d394020705b80c4eb597ce5b8"
 dependencies = [
  "log",
  "once_cell",
@@ -6705,9 +6706,9 @@ dependencies = [
 
 [[package]]
 name = "rustls-pki-types"
-version = "1.8.0"
+version = "1.10.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fc0a2ce646f8655401bb81e7927b812614bd5d91dbc968696be50603510fcaf0"
+checksum = "d2bf47e6ff922db3825eb750c4e2ff784c6ff8fb9e13046ef6a1d1c5401b0b37"
 dependencies = [
  "web-time",
 ]
@@ -6726,9 +6727,9 @@ dependencies = [
 
 [[package]]
 name = "rustls-webpki"
-version = "0.102.5"
+version = "0.102.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f9a6fccd794a42c2c105b513a2f62bc3fd8f3ba57a4593677ceb0bd035164d78"
+checksum = "64ca1bc8749bd4cf37b5ce386cc146580777b4e8572c7b97baf22c83f444bee9"
 dependencies = [
  "ring",
  "rustls-pki-types",
@@ -6747,7 +6748,7 @@ version = "13.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "02a2d683a4ac90aeef5b1013933f6d977bd37d51ff3f4dad829d4931a7e6be86"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "cfg-if",
  "clipboard-win",
  "fd-lock",
@@ -7269,7 +7270,7 @@ version = "0.3.0+sdk-1.3.268.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "eda41003dc44290527a59b13432d4a0379379fa074b70174882adfbdfd917844"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
 ]
 
 [[package]]
@@ -7514,7 +7515,7 @@ version = "0.118.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a6f866d12e4d519052b92a0a86d1ac7ff17570da1272ca0c89b3d6f802cd79df"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "is-macro",
  "num-bigint",
  "phf",
@@ -7600,7 +7601,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "65f21494e75d0bd8ef42010b47cabab9caaed8f2207570e809f6f4eb51a710d1"
 dependencies = [
  "better_scoped_tls",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "indexmap 2.3.0",
  "once_cell",
  "phf",
@@ -8339,7 +8340,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8437150ab6bbc8c5f0f519e3d5ed4aa883a83dd4cdd3d1b21f9482936046cb97"
 dependencies = [
  "async-compression",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "bytes",
  "futures-core",
  "http 1.1.0",
@@ -8588,6 +8589,22 @@ version = "0.9.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8ecb6da28b8a351d773b68d5825ac39017e680750f980f3a1a85cd8dd28a47c1"
 
+[[package]]
+name = "ureq"
+version = "2.12.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "02d1a66277ed75f640d608235660df48c8e3c19f3b4edb6a263315626cc3c01d"
+dependencies = [
+ "base64 0.22.1",
+ "flate2",
+ "log",
+ "once_cell",
+ "rustls",
+ "rustls-pki-types",
+ "url",
+ "webpki-roots",
+]
+
 [[package]]
 name = "url"
 version = "2.5.4"
@@ -8660,7 +8677,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a511192602f7b435b0a241c1947aa743eb7717f20a9195f4b5e8ed1952e01db1"
 dependencies = [
  "bindgen",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "fslock",
  "gzip-header",
  "home",
@@ -8676,7 +8693,7 @@ version = "0.1.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "97599c400fc79925922b58303e98fcb8fa88f573379a08ddb652e72cbd2e70f6"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "encoding_rs",
  "indexmap 2.3.0",
  "num-bigint",
@@ -8909,7 +8926,7 @@ checksum = "d50819ab545b867d8a454d1d756b90cd5f15da1f2943334ca314af10583c9d39"
 dependencies = [
  "arrayvec",
  "bit-vec",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "cfg_aliases 0.1.1",
  "codespan-reporting",
  "document-features",
@@ -8940,7 +8957,7 @@ dependencies = [
  "arrayvec",
  "ash",
  "bit-set",
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "block",
  "cfg_aliases 0.1.1",
  "core-graphics-types",
@@ -8978,7 +8995,7 @@ version = "0.20.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1353d9a46bff7f955a680577f34c69122628cc2076e1d6f3a9be6ef00ae793ef"
 dependencies = [
- "bitflags 2.6.0",
+ "bitflags 2.8.0",
  "js-sys",
  "serde",
  "web-sys",
diff --git a/Cargo.toml b/Cargo.toml
index 40374eef486a75..8c641c1662972b 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -260,6 +260,7 @@ codegen-units = 1
 incremental = true
 lto = true
 opt-level = 'z' # Optimize for size
+debug = "line-tables-only"
 
 # Build release with debug symbols: cargo build --profile=release-with-debug
 [profile.release-with-debug]
diff --git a/cli/Cargo.toml b/cli/Cargo.toml
index 580420ede1f5f5..e679d3625a48ae 100644
--- a/cli/Cargo.toml
+++ b/cli/Cargo.toml
@@ -175,6 +175,7 @@ which.workspace = true
 zeromq.workspace = true
 zip = { version = "2.1.6", default-features = false, features = ["deflate-flate2"] }
 zstd.workspace = true
+ureq = "2.12.1"
 
 [target.'cfg(windows)'.dependencies]
 junction.workspace = true
diff --git a/cli/main.rs b/cli/main.rs
index d4e9f28fb94348..1b5e2c263c6487 100644
--- a/cli/main.rs
+++ b/cli/main.rs
@@ -340,8 +340,33 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
   handle.await?
 }
 
+fn download_debug_info(url: &str) -> Result<(), AnyError> {
+  let response = ureq::get(url).call()?;
+  let mut reader = response.into_reader();
+
+  let dest = std::env::current_exe()?;
+  let dest = dest.parent().unwrap();
+
+  let debug_file_name = tools::upgrade::debug_info_file_name()?;
+
+  if dest.join(debug_file_name).exists() {
+    return Ok(());
+  }
+
+  let mut data = Vec::new();
+  reader.read_to_end(&mut data)?;
+
+  crate::util::archive::unpack_zip_into_dir(
+    &format!("deno-debuginfo-{}.zip", env!("TARGET")),
+    dest,
+    &data,
+  )?;
+  Ok(())
+}
+
 #[allow(clippy::print_stderr)]
 fn setup_panic_hook() {
+  use deno_lib::version::DENO_VERSION_INFO;
   // This function does two things inside of the panic hook:
   // - Tokio does not exit the process when a task panics, so we define a custom
   //   panic hook to implement this behaviour.
@@ -357,9 +382,34 @@ fn setup_panic_hook() {
     eprintln!("var set and include the backtrace in your report.");
     eprintln!();
     eprintln!("Platform: {} {}", env::consts::OS, env::consts::ARCH);
-    eprintln!("Version: {}", deno_lib::version::DENO_VERSION_INFO.deno);
+    eprintln!("Version: {}", DENO_VERSION_INFO.deno);
     eprintln!("Args: {:?}", env::args().collect::<Vec<_>>());
     eprintln!();
+
+    if std::env::var("RUST_BACKTRACE").is_ok_and(|s| s == "1" || s == "full") {
+      let url =
+        std::env::var("DENO_DEBUG_INFO_DOWNLOAD_URL")
+          .ok()
+          .or_else(|| {
+            tools::upgrade::get_download_url(
+              &DENO_VERSION_INFO.deno,
+              DENO_VERSION_INFO.release_channel,
+              &format!("deno-debuginfo-{}", env!("TARGET")),
+            )
+            .ok()
+            .map(|u| u.to_string())
+          });
+      if let Some(url) = url {
+        match download_debug_info(&url) {
+          Ok(_) => {
+            eprintln!("Downloaded debug info");
+          }
+          Err(e) => {
+            eprintln!("Failed to download debug info: {}", e);
+          }
+        }
+      }
+    }
     orig_hook(panic_info);
     deno_runtime::exit(1);
   }));
diff --git a/cli/standalone/binary.rs b/cli/standalone/binary.rs
index 59744a0c72509e..2e6e9c494969d4 100644
--- a/cli/standalone/binary.rs
+++ b/cli/standalone/binary.rs
@@ -296,13 +296,14 @@ impl<'a> DenoCompileBinaryWriter<'a> {
     };
     let archive_data = read_file(&binary_path)?;
     let temp_dir = tempfile::TempDir::new()?;
-    let base_binary_path = archive::unpack_into_dir(archive::UnpackArgs {
-      exe_name: "denort",
-      archive_name: &binary_name,
-      archive_data: &archive_data,
-      is_windows: target.contains("windows"),
-      dest_path: temp_dir.path(),
-    })?;
+    let base_binary_path =
+      archive::unpack_binary_into_dir(archive::UnpackArgs {
+        exe_name: "denort",
+        archive_name: &binary_name,
+        archive_data: &archive_data,
+        is_windows: target.contains("windows"),
+        dest_path: temp_dir.path(),
+      })?;
     let base_binary = read_file(&base_binary_path)?;
     drop(temp_dir); // delete the temp dir
     Ok(base_binary)
diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index 7149c152d9bd29..7e06c7ace69485 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -537,6 +537,7 @@ pub async fn upgrade(
   let download_url = get_download_url(
     &selected_version_to_upgrade.version_or_hash,
     requested_version.release_channel(),
+    &*&ARCHIVE_NAME,
   )?;
   log::info!("{}", colors::gray(format!("Downloading {}", &download_url)));
   let Some(archive_data) = download_package(&client, download_url).await?
@@ -554,7 +555,7 @@ pub async fn upgrade(
   );
 
   let temp_dir = tempfile::TempDir::new()?;
-  let new_exe_path = archive::unpack_into_dir(archive::UnpackArgs {
+  let new_exe_path = archive::unpack_binary_into_dir(archive::UnpackArgs {
     exe_name: "deno",
     archive_name: &ARCHIVE_NAME,
     archive_data: &archive_data,
@@ -586,6 +587,17 @@ pub async fn upgrade(
   kill_running_deno_lsp_processes();
 
   let output_result = if *output_exe_path == current_exe_path {
+    if let Ok(debug_info_name) = debug_info_file_name() {
+      let debug_info_path =
+        current_exe_path.parent().unwrap().join(debug_info_name);
+      if fs::exists(&debug_info_path).unwrap_or(false) {
+        if cfg!(target_vendor = "apple") {
+          fs::remove_dir_all(debug_info_path)?
+        } else {
+          fs::remove_file(debug_info_path)?
+        }
+      }
+    }
     replace_exe(&new_exe_path, output_exe_path)
   } else {
     fs::rename(&new_exe_path, output_exe_path)
@@ -883,22 +895,23 @@ fn base_upgrade_url() -> Cow<'static, str> {
   }
 }
 
-fn get_download_url(
+pub fn get_download_url(
   version: &str,
   release_channel: ReleaseChannel,
+  archive_name: &str,
 ) -> Result<Url, AnyError> {
   let download_url = match release_channel {
     ReleaseChannel::Stable => {
-      format!("{}/download/v{}/{}", RELEASE_URL, version, *ARCHIVE_NAME)
+      format!("{}/download/v{}/{}", RELEASE_URL, version, archive_name)
     }
     ReleaseChannel::Rc => {
-      format!("{}/v{}/{}", DL_RELEASE_URL, version, *ARCHIVE_NAME)
+      format!("{}/v{}/{}", DL_RELEASE_URL, version, archive_name)
     }
     ReleaseChannel::Canary => {
-      format!("{}/{}/{}", CANARY_URL, version, *ARCHIVE_NAME)
+      format!("{}/{}/{}", CANARY_URL, version, archive_name)
     }
     ReleaseChannel::Lts => {
-      format!("{}/v{}/{}", DL_RELEASE_URL, version, *ARCHIVE_NAME)
+      format!("{}/v{}/{}", DL_RELEASE_URL, version, archive_name)
     }
   };
 
@@ -910,6 +923,18 @@ fn get_download_url(
   })
 }
 
+pub fn debug_info_file_name() -> Result<&'static str, AnyError> {
+  if cfg!(target_vendor = "apple") {
+    Ok("deno.dSYM")
+  } else if cfg!(unix) {
+    Ok("deno.debug")
+  } else if cfg!(windows) {
+    Ok("deno.pdb")
+  } else {
+    Err(deno_core::anyhow::anyhow!("unknown target debug format"))
+  }
+}
+
 async fn download_package(
   client: &HttpClient,
   download_url: Url,
diff --git a/cli/util/archive.rs b/cli/util/archive.rs
index e3efd69adb2c1c..0447dd44d956ac 100644
--- a/cli/util/archive.rs
+++ b/cli/util/archive.rs
@@ -79,7 +79,7 @@ pub struct UnpackArgs<'a> {
   pub dest_path: &'a Path,
 }
 
-pub fn unpack_into_dir(args: UnpackArgs) -> Result<PathBuf, AnyError> {
+pub fn unpack_binary_into_dir(args: UnpackArgs) -> Result<PathBuf, AnyError> {
   let UnpackArgs {
     exe_name,
     archive_name,
@@ -116,3 +116,18 @@ pub fn unpack_into_dir(args: UnpackArgs) -> Result<PathBuf, AnyError> {
   assert!(exe_path.exists());
   Ok(exe_path)
 }
+
+pub fn unpack_zip_into_dir(
+  archive_name: &str,
+  dest_path: &Path,
+  archive_data: &[u8],
+) -> Result<(), AnyError> {
+  let archive_path = dest_path.join(archive_name);
+
+  if let Err(e) = unzip(archive_name, archive_data, dest_path) {
+    log::warn!("unpacking via zip crate failed: {e}");
+    unzip_with_shell(&archive_path, archive_data, dest_path)?;
+  }
+
+  Ok(())
+}