diff --git a/powerlevel9k.zsh-theme b/powerlevel9k.zsh-theme
index 7437fe32..081562b5 100755
--- a/powerlevel9k.zsh-theme
+++ b/powerlevel9k.zsh-theme
@@ -600,9 +600,25 @@ prompt_public_ip() {
     # Check VPN is on if VPN interface is set
     if [[ -n $POWERLEVEL9K_PUBLIC_IP_VPN_INTERFACE ]]; then
       if [[ "$OS" == "OSX" ]]; then
-        local interface="$(${ROOT_PREFIX}/sbin/ifconfig $POWERLEVEL9K_PUBLIC_IP_VPN_INTERFACE)"
-        # Check if interface is UP.
-        [[ "$interface" =~ "<UP," ]] && icon='VPN_ICON'
+        # Get a plain list of all interfaces
+        local rawInterfaces="$(${ROOT_PREFIX}/sbin/ifconfig -l)"
+        # Parse into array (split by whitespace)
+        local -a interfaces
+        interfaces=(${=rawInterfaces})
+        # Parse only relevant interface names
+        local pattern="${POWERLEVEL9K_PUBLIC_IP_VPN_INTERFACE}[^ ]?"
+        local -a relevantInterfaces
+        for rawInterface in $interfaces; do
+          [[ "$rawInterface" =~ $pattern ]] && relevantInterfaces+=( $MATCH )
+        done
+        for interfaceName in $relevantInterfaces; do
+          local interface="$(${ROOT_PREFIX}/sbin/ifconfig $interfaceName)"
+          # Check if interface is UP.
+          if [[ "$interface" =~ "<UP," ]]; then
+            icon='VPN_ICON'
+            break
+          fi
+        done
       else
         local interface=$(${ROOT_PREFIX}/sbin/ip -brief -4 a show "${POWERLEVEL9K_PUBLIC_IP_VPN_INTERFACE}")
         [[ -n "$interface" ]] && icon='VPN_ICON'
diff --git a/test/segments/public_ip.spec b/test/segments/public_ip.spec
index 8e44d0e1..39b0243c 100755
--- a/test/segments/public_ip.spec
+++ b/test/segments/public_ip.spec
@@ -42,7 +42,12 @@ function fakeIfconfig() {
   cat > $FOLDER/sbin/ifconfig <<EOF
 #!/usr/bin/env zsh
 
-if [[ "\$#" -gt 0 ]]; then
+if [[ "\$*" == "-l" ]]; then
+  echo "lo0 gif0 stf0 EHC250 EHC253 tun1 tun0 ${INTERFACE} fw0 en0 en2 en1 p2p0 bridge0 utun0"
+  exit 0
+fi
+
+if [[ "\$*" == "${INTERFACE}" ]]; then
   cat <<INNER
 ${INTERFACE}: flags=4099<UP,BROADCAST,MULTICAST>  mtu 1500
         inet 1.2.3.4  txqueuelen 1000  (Ethernet)
@@ -55,6 +60,7 @@ INNER
   exit 0
 fi
 
+if [[ "\$#" == "0" ]]; then
   cat <<INNER
 docker0: flags=4099<UP,BROADCAST,MULTICAST>  mtu 1500
         inet 172.17.0.1  netmask 255.255.0.0  broadcast 172.17.255.255
@@ -81,6 +87,7 @@ lo: flags=73<UP,LOOPBACK,RUNNING>  mtu 65536
         TX packets 5136  bytes 328651 (320.9 KiB)
         TX errors 0  dropped 0 overruns 0  carrier 0  collisions 0
 INNER
+fi
 EOF
   chmod +x $FOLDER/sbin/ifconfig
 }
@@ -346,4 +353,26 @@ function testPublicIpSegmentWithVPNTurnedOnOsx() {
   unfunction stat
 }
 
+function testPublicIpSegmentWithVPNTurnedOnAndFuzzyMatchingOnOsx() {
+  typeset -F now
+  now=$(date +%s)
+
+  local OS='OSX'
+
+  echo "1.2.3.4" > $POWERLEVEL9K_PUBLIC_IP_FILE
+  local POWERLEVEL9K_PUBLIC_IP_VPN_INTERFACE="tun"
+
+  # Fake stat call
+  function stat() {
+    echo $now
+  }
+
+  # Fake ifconfig
+  fakeIfconfig "tun3"
+
+  assertEquals "%K{000} %F{007}(vpn) %f%F{007}1.2.3.4 " "$(prompt_public_ip left 1 false "$FOLDER")"
+
+  unfunction stat
+}
+
 source shunit2/shunit2
\ No newline at end of file