diff --git a/listeners.go b/listeners.go
index 15ffbbeef92..1ae06c3d173 100644
--- a/listeners.go
+++ b/listeners.go
@@ -17,6 +17,7 @@ package caddy
 import (
 	"fmt"
 	"net"
+	"os"
 	"strconv"
 	"strings"
 	"sync"
@@ -39,6 +40,9 @@ func Listen(network, addr string) (net.Listener, error) {
 	sharedLn, _, err := listenerPool.LoadOrNew(lnKey, func() (Destructor, error) {
 		ln, err := net.Listen(network, addr)
 		if err != nil {
+			if isUnixNetwork(network) && isListenBindAddressAlreadyInUseError(err) {
+				return nil, explainUnixBindAddressAlreadyInUseError(err)
+			}
 			return nil, err
 		}
 		return &sharedListener{Listener: ln, key: lnKey}, nil
@@ -59,6 +63,9 @@ func ListenPacket(network, addr string) (net.PacketConn, error) {
 	sharedPc, _, err := listenerPool.LoadOrNew(lnKey, func() (Destructor, error) {
 		pc, err := net.ListenPacket(network, addr)
 		if err != nil {
+			if isUnixNetwork(network) && isListenBindAddressAlreadyInUseError(err) {
+				return nil, explainUnixBindAddressAlreadyInUseError(err)
+			}
 			return nil, err
 		}
 		return &sharedPacketConn{PacketConn: pc, key: lnKey}, nil
@@ -322,6 +329,44 @@ func isUnixNetwork(netw string) bool {
 	return netw == "unix" || netw == "unixgram" || netw == "unixpacket"
 }
 
+func isListenBindAddressAlreadyInUseError(err error) bool {
+	switch networkOperationError := err.(type) {
+	case *net.OpError:
+		switch syscallError := networkOperationError.Err.(type) {
+		case *os.SyscallError:
+			if syscallError.Syscall == "bind" {
+				return true
+			}
+		}
+	}
+
+	return false
+}
+
+type ErrorWithExplanation struct {
+	Explanation string
+	Err         error
+}
+
+func (e *ErrorWithExplanation) Unwrap() error { return e.Err }
+func (e *ErrorWithExplanation) Error() string {
+	if e == nil {
+		return "<nil>\n" + e.Explanation
+	}
+	return e.Err.Error() + "\n" + e.Explanation
+}
+
+func explainUnixBindAddressAlreadyInUseError(err error) error {
+	return &ErrorWithExplanation{
+		Explanation: "This can happen either when you have two programs " +
+			"(or two instances of caddy) attempting to listen on the same " +
+			"socket file at the same time, or when caddy did not exit cleanly " +
+			"last time it was run and thus did not get a chance to clean up " +
+			"the socket file on shutdown",
+		Err: err,
+	}
+}
+
 // ParseNetworkAddress parses addr into its individual
 // components. The input string is expected to be of
 // the form "network/host:port-range" where any part is