diff --git a/.circleci/config.yml b/.circleci/config.yml
index e3eb2905..95e63d81 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -291,7 +291,7 @@ workflows:
           name: x86_64-libressl-2.9
           target: x86_64-unknown-linux-gnu
           library: libressl
-          version: 2.9.0
+          version: 2.9.1
       - macos:
           name: macos
       - macos:
diff --git a/openssl-sys/build/cfgs.rs b/openssl-sys/build/cfgs.rs
index dc7240e2..c74c2bb0 100644
--- a/openssl-sys/build/cfgs.rs
+++ b/openssl-sys/build/cfgs.rs
@@ -13,6 +13,9 @@ pub fn get(openssl_version: Option<u64>, libressl_version: Option<u64>) -> Vec<&
         if libressl_version >= 0x2_07_00_00_0 {
             cfgs.push("libressl270");
         }
+        if libressl_version >= 0x2_07_01_00_0 {
+            cfgs.push("libressl271");
+        }
         if libressl_version >= 0x2_07_03_00_0 {
             cfgs.push("libressl273");
         }
@@ -22,6 +25,9 @@ pub fn get(openssl_version: Option<u64>, libressl_version: Option<u64>) -> Vec<&
         if libressl_version >= 0x2_08_01_00_0 {
             cfgs.push("libressl281");
         }
+        if libressl_version >= 0x2_09_01_00_0 {
+            cfgs.push("libressl291");
+        }
     } else {
         let openssl_version = openssl_version.unwrap();
 
diff --git a/openssl-sys/build/main.rs b/openssl-sys/build/main.rs
index a1677a69..7f803a5b 100644
--- a/openssl-sys/build/main.rs
+++ b/openssl-sys/build/main.rs
@@ -199,6 +199,7 @@ See rust-openssl README for more information:
             (8, 1) => ('8', '1'),
             (8, _) => ('8', 'x'),
             (9, 0) => ('9', '0'),
+            (9, _) => ('9', 'x'),
             _ => version_error(),
         };
 
@@ -239,7 +240,7 @@ fn version_error() -> ! {
         "
 
 This crate is only compatible with OpenSSL 1.0.1 through 1.1.1, or LibreSSL 2.5
-through 2.9.0, but a different version of OpenSSL was found. The build is now aborting
+through 2.9.x, but a different version of OpenSSL was found. The build is now aborting
 due to this version mismatch.
 
 "
diff --git a/openssl-sys/src/crypto.rs b/openssl-sys/src/crypto.rs
index 48f4e062..24e495cd 100644
--- a/openssl-sys/src/crypto.rs
+++ b/openssl-sys/src/crypto.rs
@@ -15,7 +15,13 @@ cfg_if! {
     if #[cfg(ossl110)] {
         pub const CRYPTO_EX_INDEX_SSL: c_int = 0;
         pub const CRYPTO_EX_INDEX_SSL_CTX: c_int = 1;
-
+    } else if #[cfg(libressl)] {
+        pub const CRYPTO_EX_INDEX_SSL: c_int = 1;
+        pub const CRYPTO_EX_INDEX_SSL_CTX: c_int = 2;
+    }
+}
+cfg_if! {
+    if #[cfg(any(ossl110, libressl271))] {
         extern "C" {
             pub fn OpenSSL_version_num() -> c_ulong;
             pub fn OpenSSL_version(key: c_int) -> *const c_char;
@@ -64,7 +70,7 @@ pub type CRYPTO_EX_free = unsafe extern "C" fn(
     argp: *mut c_void,
 );
 extern "C" {
-    #[cfg(ossl110)]
+    #[cfg(any(ossl110, libressl))]
     pub fn CRYPTO_get_ex_new_index(
         class_index: c_int,
         argl: c_long,
diff --git a/openssl-sys/src/ssl.rs b/openssl-sys/src/ssl.rs
index fcbac300..84db6e26 100644
--- a/openssl-sys/src/ssl.rs
+++ b/openssl-sys/src/ssl.rs
@@ -1057,7 +1057,7 @@ extern "C" {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl291))] {
         extern "C" {
             pub fn TLS_method() -> *const SSL_METHOD;
 
diff --git a/openssl/build.rs b/openssl/build.rs
index 99731c57..c1a5ccff 100644
--- a/openssl/build.rs
+++ b/openssl/build.rs
@@ -46,6 +46,10 @@ fn main() {
             println!("cargo:rustc-cfg=libressl270");
         }
 
+        if version >= 0x2_07_01_00_0 {
+            println!("cargo:rustc-cfg=libressl271");
+        }
+
         if version >= 0x2_07_03_00_0 {
             println!("cargo:rustc-cfg=libressl273");
         }
@@ -53,5 +57,9 @@ fn main() {
         if version >= 0x2_08_00_00_0 {
             println!("cargo:rustc-cfg=libressl280");
         }
+
+        if version >= 0x2_09_01_00_0 {
+            println!("cargo:rustc-cfg=libressl291");
+        }
     }
 }
diff --git a/openssl/src/ssl/mod.rs b/openssl/src/ssl/mod.rs
index f433f74d..8f173637 100644
--- a/openssl/src/ssl/mod.rs
+++ b/openssl/src/ssl/mod.rs
@@ -3831,9 +3831,14 @@ cfg_if! {
 }
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl291))] {
         use ffi::{TLS_method, DTLS_method};
-
+    } else {
+        use ffi::{SSLv23_method as TLS_method, DTLSv1_method as DTLS_method};
+    }
+}
+cfg_if! {
+    if #[cfg(ossl110)] {
         unsafe fn get_new_idx(f: ffi::CRYPTO_EX_free) -> c_int {
             ffi::CRYPTO_get_ex_new_index(
                 ffi::CRYPTO_EX_INDEX_SSL_CTX,
@@ -3856,8 +3861,6 @@ cfg_if! {
             )
         }
     } else {
-        use ffi::{SSLv23_method as TLS_method, DTLSv1_method as DTLS_method};
-
         unsafe fn get_new_idx(f: ffi::CRYPTO_EX_free) -> c_int {
             ffi::SSL_CTX_get_ex_new_index(0, ptr::null_mut(), None, None, Some(f))
         }
diff --git a/openssl/src/ssl/test/mod.rs b/openssl/src/ssl/test/mod.rs
index 136846f3..e0f3c565 100644
--- a/openssl/src/ssl/test/mod.rs
+++ b/openssl/src/ssl/test/mod.rs
@@ -306,6 +306,7 @@ fn state() {
 /// lists of supported protocols have an overlap -- with only ONE protocol
 /// being valid for both.
 #[test]
+#[cfg_attr(libressl291, ignore)]
 fn test_connect_with_srtp_ctx() {
     let listener = TcpListener::bind("127.0.0.1:0").unwrap();
     let addr = listener.local_addr().unwrap();
@@ -362,6 +363,7 @@ fn test_connect_with_srtp_ctx() {
 /// lists of supported protocols have an overlap -- with only ONE protocol
 /// being valid for both.
 #[test]
+#[cfg_attr(libressl291, ignore)]
 fn test_connect_with_srtp_ssl() {
     let listener = TcpListener::bind("127.0.0.1:0").unwrap();
     let addr = listener.local_addr().unwrap();
diff --git a/openssl/src/version.rs b/openssl/src/version.rs
index dc8508d1..0d2d5bb6 100644
--- a/openssl/src/version.rs
+++ b/openssl/src/version.rs
@@ -14,7 +14,7 @@
 use std::ffi::CStr;
 
 cfg_if! {
-    if #[cfg(ossl110)] {
+    if #[cfg(any(ossl110, libressl271))] {
         use ffi::{
             OPENSSL_VERSION, OPENSSL_CFLAGS, OPENSSL_BUILT_ON, OPENSSL_PLATFORM, OPENSSL_DIR,
             OpenSSL_version_num, OpenSSL_version,