diff --git a/.circleci/config.yml b/.circleci/config.yml
index 2cc6cced..0e6f90e0 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -108,9 +108,9 @@ openssl_101: &OPENSSL_101
 libressl_250: &LIBRESSL_250
   LIBRARY: libressl
   VERSION: 2.5.0
-libressl_270: &LIBRESSL_272
+libressl_270: &LIBRESSL_280
   LIBRARY: libressl
-  VERSION: 2.7.2
+  VERSION: 2.8.0
 
 x86_64: &X86_64
   TARGET: x86_64-unknown-linux-gnu
@@ -195,10 +195,10 @@ jobs:
     <<: *JOB
     environment:
       <<: [*LIBRESSL_250, *X86_64, *BASE]
-  x86_64-libressl-2.7.2:
+  x86_64-libressl-2.8.0:
     <<: *JOB
     environment:
-      <<: [*LIBRESSL_272, *X86_64, *BASE]
+      <<: [*LIBRESSL_280, *X86_64, *BASE]
   macos:
     <<: *MACOS_JOB
     environment:
@@ -226,6 +226,6 @@ workflows:
     - armhf-openssl-1.1.0
     - armhf-openssl-1.0.2
     - x86_64-libressl-2.5.0
-    - x86_64-libressl-2.7.2
+    - x86_64-libressl-2.8.0
     - macos
     - macos-vendored
diff --git a/openssl-sys/build/cfgs.rs b/openssl-sys/build/cfgs.rs
index 38bacdf3..cfd85cbb 100644
--- a/openssl-sys/build/cfgs.rs
+++ b/openssl-sys/build/cfgs.rs
@@ -16,6 +16,9 @@ pub fn get(openssl_version: Option<u64>, libressl_version: Option<u64>) -> Vec<&
         if libressl_version >= 0x2_07_03_00_0 {
             cfgs.push("libressl273");
         }
+        if libressl_version >= 0x2_08_00_00_0 {
+            cfgs.push("libressl280");
+        }
     } else {
         let openssl_version = openssl_version.unwrap();
 
diff --git a/openssl-sys/build/main.rs b/openssl-sys/build/main.rs
index 4d58d248..4c615401 100644
--- a/openssl-sys/build/main.rs
+++ b/openssl-sys/build/main.rs
@@ -497,6 +497,7 @@ See rust-openssl README for more information:
             (6, 2) => ('6', '2'),
             (6, _) => ('6', 'x'),
             (7, _) => ('7', 'x'),
+            (8, 0) => ('8', 'x'),
             _ => version_error(),
         };
 
diff --git a/openssl-sys/src/asn1.rs b/openssl-sys/src/asn1.rs
index 9cf321ea..90eaeffa 100644
--- a/openssl-sys/src/asn1.rs
+++ b/openssl-sys/src/asn1.rs
@@ -49,7 +49,7 @@ extern "C" {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn ASN1_STRING_to_UTF8(out: *mut *mut c_uchar, s: *const ASN1_STRING) -> c_int;
         }
diff --git a/openssl-sys/src/bio.rs b/openssl-sys/src/bio.rs
index ce660145..b6bde933 100644
--- a/openssl-sys/src/bio.rs
+++ b/openssl-sys/src/bio.rs
@@ -36,7 +36,7 @@ pub type bio_info_cb =
     Option<unsafe extern "C" fn(*mut BIO, c_int, *const c_char, c_int, c_long, c_long)>;
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum BIO_METHOD {}
     } else {
         #[repr(C)]
@@ -60,24 +60,14 @@ pub unsafe fn BIO_get_mem_data(b: *mut BIO, pp: *mut *mut c_char) -> c_long {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn BIO_s_file() -> *const BIO_METHOD;
-        }
-    } else {
-        extern "C" {
-            pub fn BIO_s_file() -> *mut BIO_METHOD;
-        }
-    }
-}
-cfg_if! {
-    if #[cfg(ossl110)] {
-        extern "C" {
             pub fn BIO_new(type_: *const BIO_METHOD) -> *mut BIO;
         }
     } else {
         extern "C" {
-            pub fn BIO_new(type_: *mut BIO_METHOD) -> *mut BIO;
+            pub fn BIO_s_file() -> *mut BIO_METHOD;
         }
     }
 }
@@ -96,7 +86,7 @@ extern "C" {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn BIO_s_mem() -> *const BIO_METHOD;
         }
@@ -107,7 +97,7 @@ cfg_if! {
     }
 }
 cfg_if! {
-    if #[cfg(ossl102)] {
+    if #[cfg(any(ossl102, libressl280))] {
         extern "C" {
             pub fn BIO_new_mem_buf(buf: *const c_void, len: c_int) -> *mut BIO;
         }
diff --git a/openssl-sys/src/ec.rs b/openssl-sys/src/ec.rs
index 3eea0d24..a33d4d46 100644
--- a/openssl-sys/src/ec.rs
+++ b/openssl-sys/src/ec.rs
@@ -166,7 +166,7 @@ extern "C" {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum ECDSA_SIG {}
     } else {
         #[repr(C)]
diff --git a/openssl-sys/src/evp.rs b/openssl-sys/src/evp.rs
index c78f7616..53d2e22f 100644
--- a/openssl-sys/src/evp.rs
+++ b/openssl-sys/src/evp.rs
@@ -108,19 +108,28 @@ extern "C" {
         e: *mut ENGINE,
         pkey: *mut EVP_PKEY,
     ) -> c_int;
-    #[cfg(not(ossl102))]
-    pub fn EVP_DigestVerifyFinal(
-        ctx: *mut EVP_MD_CTX,
-        sigret: *mut c_uchar,
-        siglen: size_t,
-    ) -> c_int;
-    #[cfg(ossl102)]
-    pub fn EVP_DigestVerifyFinal(
-        ctx: *mut EVP_MD_CTX,
-        sigret: *const c_uchar,
-        siglen: size_t,
-    ) -> c_int;
+}
+cfg_if! {
+    if #[cfg(any(ossl102, libressl280))] {
+        extern "C" {
+            pub fn EVP_DigestVerifyFinal(
+                ctx: *mut EVP_MD_CTX,
+                sigret: *const c_uchar,
+                siglen: size_t,
+            ) -> c_int;
+        }
+    } else {
+        extern "C" {
+            pub fn EVP_DigestVerifyFinal(
+                ctx: *mut EVP_MD_CTX,
+                sigret: *mut c_uchar,
+                siglen: size_t,
+            ) -> c_int;
+        }
+    }
+}
 
+extern "C" {
     pub fn EVP_CIPHER_CTX_new() -> *mut EVP_CIPHER_CTX;
     pub fn EVP_CIPHER_CTX_free(ctx: *mut EVP_CIPHER_CTX);
     pub fn EVP_MD_CTX_copy_ex(dst: *mut EVP_MD_CTX, src: *const EVP_MD_CTX) -> c_int;
@@ -181,7 +190,7 @@ extern "C" {
     pub fn EVP_PKEY_id(pkey: *const EVP_PKEY) -> c_int;
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn EVP_PKEY_bits(key: *const EVP_PKEY) -> c_int;
         }
diff --git a/openssl-sys/src/ossl_typ.rs b/openssl-sys/src/ossl_typ.rs
index 58cab8d7..96c4d002 100644
--- a/openssl-sys/src/ossl_typ.rs
+++ b/openssl-sys/src/ossl_typ.rs
@@ -13,7 +13,7 @@ pub enum ASN1_OBJECT {}
 
 pub enum bio_st {} // FIXME remove
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum BIO {}
     } else {
         #[repr(C)]
@@ -59,7 +59,7 @@ pub enum BN_CTX {}
 pub enum BN_GENCB {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum EVP_CIPHER {}
     } else {
         #[repr(C)]
@@ -90,7 +90,7 @@ cfg_if! {
 pub enum EVP_CIPHER_CTX {}
 pub enum EVP_MD {}
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum EVP_MD_CTX {}
     } else {
         #[repr(C)]
@@ -105,7 +105,7 @@ cfg_if! {
     }
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum EVP_PKEY {}
     } else {
         #[repr(C)]
@@ -127,7 +127,7 @@ pub enum EVP_PKEY_ASN1_METHOD {}
 pub enum EVP_PKEY_CTX {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum HMAC_CTX {}
     } else {
         #[repr(C)]
@@ -143,7 +143,7 @@ cfg_if! {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum DH {}
     } else {
         #[repr(C)]
@@ -172,7 +172,7 @@ cfg_if! {
 pub enum DH_METHOD {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum DSA {}
     } else {
         #[repr(C)]
@@ -201,7 +201,7 @@ cfg_if! {
 pub enum DSA_METHOD {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum RSA {}
     } else if #[cfg(libressl)] {
         #[repr(C)]
@@ -267,7 +267,7 @@ pub enum RSA_METHOD {}
 pub enum EC_KEY {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum X509 {}
     } else if #[cfg(libressl)] {
         #[repr(C)]
@@ -344,7 +344,7 @@ pub enum X509_STORE {}
 pub enum X509_STORE_CTX {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum X509_VERIFY_PARAM {} 
     } else if #[cfg(libressl251)] {
         #[repr(C)]
@@ -406,7 +406,7 @@ pub enum OPENSSL_INIT_SETTINGS {}
 
 pub enum ENGINE {}
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum SSL {}
     } else if #[cfg(libressl251)] {
         #[repr(C)]
@@ -708,7 +708,7 @@ cfg_if! {
     }
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum SSL_CTX {}
     } else if #[cfg(libressl251)] {
         #[repr(C)]
@@ -970,7 +970,7 @@ cfg_if! {
 pub enum COMP_METHOD {}
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum CRYPTO_EX_DATA {}
     } else if #[cfg(libressl)] {
         #[repr(C)]
diff --git a/openssl-sys/src/pkcs12.rs b/openssl-sys/src/pkcs12.rs
index 72170ea1..9cdba7e1 100644
--- a/openssl-sys/src/pkcs12.rs
+++ b/openssl-sys/src/pkcs12.rs
@@ -18,7 +18,7 @@ extern "C" {
     ) -> c_int;
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn PKCS12_create(
                 pass: *const c_char,
diff --git a/openssl-sys/src/ssl.rs b/openssl-sys/src/ssl.rs
index 39b165f1..e139a89c 100644
--- a/openssl-sys/src/ssl.rs
+++ b/openssl-sys/src/ssl.rs
@@ -25,7 +25,7 @@ pub const SSL_FILETYPE_ASN1: c_int = X509_FILETYPE_ASN1;
 pub enum SSL_METHOD {}
 pub enum SSL_CIPHER {}
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         pub enum SSL_SESSION {}
     } else if #[cfg(libressl251)] {
         #[repr(C)]
@@ -292,7 +292,13 @@ cfg_if! {
 pub const SSL_OP_ENABLE_MIDDLEBOX_COMPAT: c_ulong = 0x00100000;
 
 pub const SSL_OP_CIPHER_SERVER_PREFERENCE: c_ulong = 0x00400000;
-pub const SSL_OP_TLS_ROLLBACK_BUG: c_ulong = 0x00800000;
+cfg_if! {
+    if #[cfg(libressl280)] {
+        pub const SSL_OP_TLS_ROLLBACK_BUG: c_ulong = 0;
+    } else {
+        pub const SSL_OP_TLS_ROLLBACK_BUG: c_ulong = 0x00800000;
+    }
+}
 
 
 cfg_if! {
@@ -466,7 +472,7 @@ extern "C" {
     );
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn SSL_CTX_sess_set_get_cb(
                 ctx: *mut ::SSL_CTX,
@@ -497,7 +503,7 @@ extern "C" {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn SSL_CTX_set_cookie_verify_cb(
                 s: *mut SSL_CTX,
@@ -843,7 +849,7 @@ extern "C" {
     pub fn SSL_CIPHER_get_bits(cipher: *const SSL_CIPHER, alg_bits: *mut c_int) -> c_int;
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn SSL_CIPHER_get_version(cipher: *const SSL_CIPHER) -> *const c_char;
         }
@@ -1036,11 +1042,20 @@ extern "C" {
     ) -> *mut c_char;
 
     pub fn SSL_get_certificate(ssl: *const SSL) -> *mut X509;
-    #[cfg(not(ossl102))]
-    pub fn SSL_get_privatekey(ssl: *mut SSL) -> *mut EVP_PKEY;
-    #[cfg(ossl102)]
-    pub fn SSL_get_privatekey(ssl: *const SSL) -> *mut EVP_PKEY;
+}
+cfg_if! {
+    if #[cfg(any(ossl102, libressl280))] {
+        extern "C" {
+            pub fn SSL_get_privatekey(ssl: *const SSL) -> *mut EVP_PKEY;
+        }
+    } else {
+        extern "C" {
+            pub fn SSL_get_privatekey(ssl: *mut SSL) -> *mut EVP_PKEY;
+        }
+    }
+}
 
+extern "C" {
     #[cfg(ossl102)]
     pub fn SSL_CTX_get0_certificate(ctx: *const SSL_CTX) -> *mut X509;
     #[cfg(ossl102)]
diff --git a/openssl-sys/src/x509.rs b/openssl-sys/src/x509.rs
index 1a9018a9..a0da2069 100644
--- a/openssl-sys/src/x509.rs
+++ b/openssl-sys/src/x509.rs
@@ -191,7 +191,7 @@ extern "C" {
     pub fn X509_set_issuer_name(x: *mut X509, name: *mut X509_NAME) -> c_int;
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn X509_get_issuer_name(x: *const ::X509) -> *mut ::X509_NAME;
         }
@@ -205,15 +205,24 @@ extern "C" {
     pub fn X509_set_subject_name(x: *mut X509, name: *mut X509_NAME) -> c_int;
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn X509_get_subject_name(x: *const ::X509) -> *mut ::X509_NAME;
+        }
+    } else {
+        extern "C" {
+            pub fn X509_get_subject_name(x: *mut ::X509) -> *mut ::X509_NAME;
+        }
+    }
+}
+cfg_if! {
+    if #[cfg(ossl110)] {
+        extern "C" {
             pub fn X509_set1_notBefore(x: *mut ::X509, tm: *const ::ASN1_TIME) -> c_int;
             pub fn X509_set1_notAfter(x: *mut ::X509, tm: *const ::ASN1_TIME) -> c_int;
         }
     } else {
         extern "C" {
-            pub fn X509_get_subject_name(x: *mut ::X509) -> *mut ::X509_NAME;
             pub fn X509_set_notBefore(x: *mut ::X509, tm: *const ::ASN1_TIME) -> c_int;
             pub fn X509_set_notAfter(x: *mut ::X509, tm: *const ::ASN1_TIME) -> c_int;
         }
@@ -244,7 +253,7 @@ extern "C" {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn X509_NAME_entry_count(n: *const X509_NAME) -> c_int;
         }
@@ -255,11 +264,19 @@ cfg_if! {
     }
 }
 
-extern "C" {
-    pub fn X509_NAME_get_index_by_NID(n: *mut X509_NAME, nid: c_int, last_pos: c_int) -> c_int;
+cfg_if! {
+    if #[cfg(libressl280)] {
+        extern "C" {
+            pub fn X509_NAME_get_index_by_NID(n: *const X509_NAME, nid: c_int, last_pos: c_int) -> c_int;
+        }
+    } else {
+        extern "C" {
+            pub fn X509_NAME_get_index_by_NID(n: *mut X509_NAME, nid: c_int, last_pos: c_int) -> c_int;
+        }
+    }
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn X509_NAME_get_entry(n: *const X509_NAME, loc: c_int) -> *mut X509_NAME_ENTRY;
             pub fn X509_NAME_add_entry_by_NID(
@@ -305,7 +322,7 @@ extern "C" {
     pub fn X509_add_ext(x: *mut X509, ext: *mut X509_EXTENSION, loc: c_int) -> c_int;
 }
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn X509_get_ext_d2i(
                 x: *const ::X509,
diff --git a/openssl-sys/src/x509v3.rs b/openssl-sys/src/x509v3.rs
index 81203526..d355a549 100644
--- a/openssl-sys/src/x509v3.rs
+++ b/openssl-sys/src/x509v3.rs
@@ -41,7 +41,7 @@ pub const X509_CHECK_FLAG_SINGLE_LABEL_SUBDOMAINS: c_uint = 0x10;
 pub const X509_CHECK_FLAG_NEVER_CHECK_SUBJECT: c_uint = 0x20;
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl280))] {
         extern "C" {
             pub fn X509V3_EXT_nconf_nid(
                 conf: *mut CONF,
diff --git a/openssl/build.rs b/openssl/build.rs
index f1166d62..99731c57 100644
--- a/openssl/build.rs
+++ b/openssl/build.rs
@@ -49,5 +49,9 @@ fn main() {
         if version >= 0x2_07_03_00_0 {
             println!("cargo:rustc-cfg=libressl273");
         }
+
+        if version >= 0x2_08_00_00_0 {
+            println!("cargo:rustc-cfg=libressl280");
+        }
     }
 }
diff --git a/openssl/src/ssl/callbacks.rs b/openssl/src/ssl/callbacks.rs
index c9779416..daa58a4e 100644
--- a/openssl/src/ssl/callbacks.rs
+++ b/openssl/src/ssl/callbacks.rs
@@ -379,10 +379,13 @@ pub unsafe extern "C" fn raw_remove_session<F>(
     callback(ctx, session)
 }
 
-#[cfg(ossl110)]
-type DataPtr = *const c_uchar;
-#[cfg(not(ossl110))]
-type DataPtr = *mut c_uchar;
+cfg_if! {
+    if #[cfg(any(ossl110, libressl280))] {
+        type DataPtr = *const c_uchar;
+    } else {
+        type DataPtr = *mut c_uchar;
+    }
+}
 
 pub unsafe extern "C" fn raw_get_session<F>(
     ssl: *mut ffi::SSL,
@@ -503,11 +506,13 @@ where
     }
 }
 
-#[cfg(ossl110)]
-type CookiePtr = *const c_uchar;
-
-#[cfg(not(ossl110))]
-type CookiePtr = *mut c_uchar;
+cfg_if! {
+    if #[cfg(any(ossl110, libressl280))] {
+        type CookiePtr = *const c_uchar;
+    } else {
+        type CookiePtr = *mut c_uchar;
+    }
+}
 
 pub extern "C" fn raw_cookie_verify<F>(
     ssl: *mut ffi::SSL,