diff --git a/CHANGELOG_PENDING.md b/CHANGELOG_PENDING.md
index 36c64be5e..d628bc598 100644
--- a/CHANGELOG_PENDING.md
+++ b/CHANGELOG_PENDING.md
@@ -20,3 +20,5 @@
 
 ### BUG FIXES:
 - [state] [\#3537](https://github.com/tendermint/tendermint/pull/3537#issuecomment-482711833) LoadValidators: do not return an empty validator set
+- [p2p] \#3532 limit the number of attempts to connect to a peer in seed mode
+  to 16 (as a result, the node will stop retrying after a 35 hours time window)
diff --git a/p2p/pex/pex_reactor.go b/p2p/pex/pex_reactor.go
index c24ee983c..38befe29a 100644
--- a/p2p/pex/pex_reactor.go
+++ b/p2p/pex/pex_reactor.go
@@ -48,6 +48,24 @@ const (
 	biasToSelectNewPeers = 30 // 70 to select good peers
 )
 
+type errMaxAttemptsToDial struct {
+}
+
+func (e errMaxAttemptsToDial) Error() string {
+	return fmt.Sprintf("reached max attempts %d to dial", maxAttemptsToDial)
+}
+
+type errTooEarlyToDial struct {
+	backoffDuration time.Duration
+	lastDialed      time.Time
+}
+
+func (e errTooEarlyToDial) Error() string {
+	return fmt.Sprintf(
+		"too early to dial (backoff duration: %d, last dialed: %v, time since: %v)",
+		e.backoffDuration, e.lastDialed, time.Since(e.lastDialed))
+}
+
 // PEXReactor handles PEX (peer exchange) and ensures that an
 // adequate number of peers are connected to the switch.
 //
@@ -449,7 +467,19 @@ func (r *PEXReactor) ensurePeers() {
 
 	// Dial picked addresses
 	for _, addr := range toDial {
-		go r.dialPeer(addr)
+		go func(addr *p2p.NetAddress) {
+			err := r.dialPeer(addr)
+			if err != nil {
+				switch err.(type) {
+				case errMaxAttemptsToDial:
+					r.Logger.Debug(err.Error(), "addr", addr)
+				case errTooEarlyToDial:
+					r.Logger.Debug(err.Error(), "addr", addr)
+				default:
+					r.Logger.Error(err.Error(), "addr", addr)
+				}
+			}
+		}(addr)
 	}
 
 	// If we need more addresses, pick a random peer and ask for more.
@@ -479,17 +509,16 @@ func (r *PEXReactor) dialAttemptsInfo(addr *p2p.NetAddress) (attempts int, lastD
 	return atd.number, atd.lastDialed
 }
 
-func (r *PEXReactor) dialPeer(addr *p2p.NetAddress) {
+func (r *PEXReactor) dialPeer(addr *p2p.NetAddress) error {
 	attempts, lastDialed := r.dialAttemptsInfo(addr)
 
 	if attempts > maxAttemptsToDial {
-		// Do not log the message if the addr gets readded.
-		if attempts+1 == maxAttemptsToDial {
-			r.Logger.Info("Reached max attempts to dial", "addr", addr, "attempts", attempts)
-			r.attemptsToDial.Store(addr.DialString(), _attemptsToDial{attempts + 1, time.Now()})
-		}
+		// TODO(melekes): have a blacklist in the addrbook with peers whom we've
+		// failed to connect to. Then we can clean up attemptsToDial, which acts as
+		// a blacklist currently.
+		// https://github.com/tendermint/tendermint/issues/3572
 		r.book.MarkBad(addr)
-		return
+		return errMaxAttemptsToDial{}
 	}
 
 	// exponential backoff if it's not our first attempt to dial given address
@@ -498,33 +527,31 @@ func (r *PEXReactor) dialPeer(addr *p2p.NetAddress) {
 		backoffDuration := jitterSeconds + ((1 << uint(attempts)) * time.Second)
 		sinceLastDialed := time.Since(lastDialed)
 		if sinceLastDialed < backoffDuration {
-			r.Logger.Debug("Too early to dial", "addr", addr, "backoff_duration", backoffDuration, "last_dialed", lastDialed, "time_since", sinceLastDialed)
-			return
+			return errTooEarlyToDial{backoffDuration, lastDialed}
 		}
 	}
 
 	err := r.Switch.DialPeerWithAddress(addr, false)
+
 	if err != nil {
 		if _, ok := err.(p2p.ErrCurrentlyDialingOrExistingAddress); ok {
-			return
+			return err
 		}
 
-		r.Logger.Error("Dialing failed", "addr", addr, "err", err, "attempts", attempts)
 		markAddrInBookBasedOnErr(addr, r.book, err)
-		if _, ok := err.(p2p.ErrSwitchAuthenticationFailure); ok {
+		switch err.(type) {
+		case p2p.ErrSwitchAuthenticationFailure:
+			// NOTE: addr is removed from addrbook in markAddrInBookBasedOnErr
 			r.attemptsToDial.Delete(addr.DialString())
-		} else {
-			// FIXME: if the addr is going to be removed from the addrbook (hard to
-			// tell at this point), we need to Delete it from attemptsToDial, not
-			// record another attempt.
-			// record attempt
+		default:
 			r.attemptsToDial.Store(addr.DialString(), _attemptsToDial{attempts + 1, time.Now()})
 		}
-		return
+		return errors.Wrapf(err, "dialing failed (attempts: %d)", attempts+1)
 	}
 
 	// cleanup any history
 	r.attemptsToDial.Delete(addr.DialString())
+	return nil
 }
 
 // checkSeeds checks that addresses are well formed.
@@ -633,14 +660,16 @@ func (r *PEXReactor) crawlPeers(addrs []*p2p.NetAddress) {
 			LastCrawled: now,
 		}
 
-		err := r.Switch.DialPeerWithAddress(addr, false)
+		err := r.dialPeer(addr)
 		if err != nil {
-			if _, ok := err.(p2p.ErrCurrentlyDialingOrExistingAddress); ok {
-				continue
+			switch err.(type) {
+			case errMaxAttemptsToDial:
+				r.Logger.Debug(err.Error(), "addr", addr)
+			case errTooEarlyToDial:
+				r.Logger.Debug(err.Error(), "addr", addr)
+			default:
+				r.Logger.Error(err.Error(), "addr", addr)
 			}
-
-			r.Logger.Error("Dialing failed", "addr", addr, "err", err)
-			markAddrInBookBasedOnErr(addr, r.book, err)
 			continue
 		}
 
diff --git a/p2p/pex/pex_reactor_test.go b/p2p/pex/pex_reactor_test.go
index 077f07a60..6572a5f61 100644
--- a/p2p/pex/pex_reactor_test.go
+++ b/p2p/pex/pex_reactor_test.go
@@ -322,6 +322,34 @@ func TestPEXReactorSeedMode(t *testing.T) {
 	assert.Equal(t, 0, sw.Peers().Size())
 }
 
+func TestPEXReactorDialsPeerUpToMaxAttemptsInSeedMode(t *testing.T) {
+	// directory to store address books
+	dir, err := ioutil.TempDir("", "pex_reactor")
+	require.Nil(t, err)
+	defer os.RemoveAll(dir) // nolint: errcheck
+
+	pexR, book := createReactor(&PEXReactorConfig{SeedMode: true})
+	defer teardownReactor(book)
+
+	sw := createSwitchAndAddReactors(pexR)
+	sw.SetAddrBook(book)
+	err = sw.Start()
+	require.NoError(t, err)
+	defer sw.Stop()
+
+	peer := mock.NewPeer(nil)
+	addr := peer.SocketAddr()
+
+	err = book.AddAddress(addr, addr)
+	require.NoError(t, err)
+
+	assert.True(t, book.HasAddress(addr))
+	// imitate maxAttemptsToDial reached
+	pexR.attemptsToDial.Store(addr.DialString(), _attemptsToDial{maxAttemptsToDial + 1, time.Now()})
+	pexR.crawlPeers([]*p2p.NetAddress{addr})
+	assert.False(t, book.HasAddress(addr))
+}
+
 // connect a peer to a seed, wait a bit, then stop it.
 // this should give it time to request addrs and for the seed
 // to call FlushStop, and allows us to test calling Stop concurrently