diff --git a/net/httping/Portfile b/net/httping/Portfile
index 80ea7f09ae7..97bdd088bb7 100644
--- a/net/httping/Portfile
+++ b/net/httping/Portfile
@@ -5,11 +5,11 @@ PortGroup           cmake 1.1
 PortGroup           github 1.0
 PortGroup           openssl 1.0
 
-github.setup        folkertvanheusden HTTPing 3.6 v
-revision            1
-checksums           rmd160  8b6bc14a6d09461ef7dea606d7a2059ea6b12284 \
-                    sha256  d332fc5436bcf8290bcb4fe75b7019b90facfb64264dc3c7bc3407da27c18d77 \
-                    size    83122
+github.setup        folkertvanheusden HTTPing 4.4.0 v
+revision            0
+checksums           rmd160  1b313b818b6dddff42dbb57ea20ca8ec00758ffc \
+                    sha256  87fa2da5ac83c4a0edf4086161815a632df38e1cc230e1e8a24a8114c09da8fd \
+                    size    82454
 
 name                httping
 categories          net www
@@ -37,13 +37,13 @@ depends_lib         port:fftw-3 \
 
 installs_libs       no
 
+# Remove these patches in the next release
 patchfiles          patch-tcp.c.diff
+patchfiles-append   define-no-tfo.diff
 
-configure.args      -DCMAKE_EXE_LINKER_FLAGS="-lintl"
-
-destroot {
-    copy ${workpath}/build/httping ${destroot}${prefix}/bin/
-    copy ${worksrcpath}/httping.1 ${destroot}${prefix}/share/man/man1/
-}
-
-github.livecheck.regex  {(\d\.\d)}
+configure.args-append \
+                    -DUSE_SSL=ON \
+                    -DUSE_GETTEXT=ON \
+                    -DUSE_TUI=ON \
+                    -DUSE_FFTW3=ON \
+                    -DCMAKE_INSTALL_MANDIR="${prefix}/share/man/man1/"
diff --git a/net/httping/files/define-no-tfo.diff b/net/httping/files/define-no-tfo.diff
new file mode 100644
index 00000000000..e915be1fb7c
--- /dev/null
+++ b/net/httping/files/define-no-tfo.diff
@@ -0,0 +1,98 @@
+# Define NO_TFO on macOS < 10.11
+# See: https://github.com/folkertvanheusden/HTTPing/pull/22
+
+--- gen.h.orig
++++ gen.h
+@@ -34,6 +34,13 @@
+ #define gettext(x) (x)
+ #endif
+ 
++#ifdef __APPLE__
++#include <AvailabilityMacros.h>
++#if MAC_OS_X_VERSION_MIN_REQUIRED < 101100
++#define NO_TFO
++#endif
++#endif
++
+ typedef struct
+ {
+ 	double cur, min, avg, max, sd, med;
+--- help.c.orig
++++ help.c
+@@ -71,7 +71,9 @@ void version(void)
+ #endif
+ #endif
+ 
++#ifndef NO_TFO
+ 	fprintf(stderr, gettext(" * TFO (TCP fast open) support included (-F)\n"));
++#endif
+ 	fprintf(stderr, gettext("\n"));
+ }
+ 
+@@ -207,7 +209,9 @@ void usage(const char *me)
+ 	format_help("-r", "--resolve-once", gettext("resolve hostname only once (useful when pinging roundrobin DNS: also takes the first DNS lookup out of the loop so that the first measurement is also correct)"));
+ 	format_help("-W", NULL, gettext("do not abort the program if resolving failed: keep retrying"));
+ 	format_help("-y x", "--bind-to", gettext("bind to an ip-address (and thus interface) with an optional port"));
++#ifndef NO_TFO
+ 	format_help("-F", "--tcp-fast-open", gettext("\"TCP fast open\" (TFO), reduces the latency of TCP connects"));
++#endif
+ #ifdef linux
+ 	format_help(NULL, "--priority", gettext("set priority of packets"));
+ #endif
+--- main.c.orig
++++ main.c
+@@ -1396,7 +1396,11 @@ int main(int argc, char *argv[])
+ 				break;
+ 
+ 			case 'F':
++#ifdef NO_TFO
++                fprintf(stderr, gettext("Warning: TCP TFO is not supported. Disabling.\n"));
++#else
+ 				use_tfo = 1;
++#endif
+ 				break;
+ 
+ 			case 22:
+@@ -2157,7 +2161,7 @@ int main(int argc, char *argv[])
+ #if defined(linux) || defined(__FreeBSD__)
+ 			if (getsockopt(fd, IPPROTO_TCP, TCP_INFO, &info, &info_len) == 0)
+ 			{
+-#ifdef TCPI_OPT_SYN_DATA
++#if defined(TCPI_OPT_SYN_DATA) && !defined(NO_TFO)
+ 				if (info.tcpi_options & TCPI_OPT_SYN_DATA)
+ 					tfo_success = 1;
+ #endif
+@@ -2345,8 +2349,10 @@ int main(int argc, char *argv[])
+ #endif
+ 				}
+ 
++#ifndef NO_TFO
+ 				if (tfo_success)
+ 					str_add(&line, " F");
++#endif
+ 
+ #if HAVE_NCURSES
+ 				if (ncurses_mode)
+--- tcp.c.orig
++++ tcp.c
+@@ -159,6 +159,12 @@ int connect_to(int fd, struct addrinfo *ai, double timeout, char *tfo, char *msg
+ 	to.tv_usec = (long)(timeout * 1000.0) % 1000000;
+ 
+ 	/* connect to peer */
++#ifdef NO_TFO
++	(void)tfo;
++	(void)msg;
++	(void)msg_len;
++	(void)msg_accepted;
++#else
+ 	if (tfo && *tfo)
+ 	{
+ #if defined(__FreeBSD__)
+@@ -182,6 +188,7 @@ int connect_to(int fd, struct addrinfo *ai, double timeout, char *tfo, char *msg
+ 		}
+ 	}
+ 	else
++#endif
+ 	{
+ 		int rc = -1;
+ 
diff --git a/net/httping/files/patch-tcp.c.diff b/net/httping/files/patch-tcp.c.diff
index dae5b57d87d..64be503c787 100644
--- a/net/httping/files/patch-tcp.c.diff
+++ b/net/httping/files/patch-tcp.c.diff
@@ -1,20 +1,26 @@
+# Enable TCP Fast Open on macOS
+# See: https://github.com/folkertvanheusden/HTTPing/pull/48
+
 --- tcp.c.orig	2024-05-08 01:54:44
 +++ tcp.c	2024-05-10 16:16:28
-@@ -161,14 +161,14 @@
+@@ -161,15 +161,15 @@
  	/* connect to peer */
  	if (tfo && *tfo)
  	{
 -#if defined(__FreeBSD__)
-+/* #if defined(__FreeBSD__) */
- 		int enable = 1;                                                                                                                                                                                             
- 		setsockopt(fd, IPPROTO_TCP, TCP_FASTOPEN, &enable, sizeof(enable));                                                                                                                                         
+-		int enable = 1;                                                                                                                                                                                             
+-		setsockopt(fd, IPPROTO_TCP, TCP_FASTOPEN, &enable, sizeof(enable));                                                                                                                                         
++#if defined(__FreeBSD__) || defined(__APPLE__)
++		int enable = 1;
++		setsockopt(fd, IPPROTO_TCP, TCP_FASTOPEN, &enable, sizeof(enable));
  
- 		rc = sendto(fd, msg, msg_len, 0, ai->ai_addr, ai->ai_addrlen);                                                                                                                                              
--#else
-+/* #else
+-		rc = sendto(fd, msg, msg_len, 0, ai->ai_addr, ai->ai_addrlen);                                                                                                                                              
++		rc = sendto(fd, msg, msg_len, 0, ai->ai_addr, ai->ai_addrlen);
+ #else
  		rc = sendto(fd, msg, msg_len, MSG_FASTOPEN, ai -> ai_addr, ai -> ai_addrlen);
--#endif
-+#endif */
- 		
+ #endif
+-		
++
  		if (rc == msg_len)
  			*msg_accepted = 1;
+ 		if (errno == 0)