diff --git a/.aegir.js b/.aegir.js
index 18d6236a58..df4a41f5f8 100644
--- a/.aegir.js
+++ b/.aegir.js
@@ -45,7 +45,7 @@ const after = async () => {
 }
 
 module.exports = {
-  bundlesize: { maxSize: '200kB' },
+  bundlesize: { maxSize: '202kB' },
   hooks: {
     pre: before,
     post: after
diff --git a/doc/CONFIGURATION.md b/doc/CONFIGURATION.md
index 6a0bb44e02..17174bb1ef 100644
--- a/doc/CONFIGURATION.md
+++ b/doc/CONFIGURATION.md
@@ -270,7 +270,7 @@ const node = await Libp2p.create({
   },
   config: {
     peerDiscovery: {
-      autoDial: true,             // Auto connect to discovered peers (limited by ConnectionManager minPeers)
+      autoDial: true,             // Auto connect to discovered peers (limited by ConnectionManager minConnections)
       // The `tag` property will be searched when creating the instance of your Peer Discovery service.
       // The associated object, will be passed to the service when it is instantiated.
       [MulticastDNS.tag]: {
diff --git a/doc/GETTING_STARTED.md b/doc/GETTING_STARTED.md
index 216110c4a6..8b50efd7e0 100644
--- a/doc/GETTING_STARTED.md
+++ b/doc/GETTING_STARTED.md
@@ -217,7 +217,7 @@ const node = await Libp2p.create({
   },
   config: {
     peerDiscovery: {
-      autoDial: true, // Auto connect to discovered peers (limited by ConnectionManager minPeers)
+      autoDial: true, // Auto connect to discovered peers (limited by ConnectionManager minConnections)
       // The `tag` property will be searched when creating the instance of your Peer Discovery service.
       // The associated object, will be passed to the service when it is instantiated.
       [Bootstrap.tag]: {
diff --git a/src/config.js b/src/config.js
index f586c6dc87..7e3d630efe 100644
--- a/src/config.js
+++ b/src/config.js
@@ -12,7 +12,7 @@ const DefaultConfig = {
     noAnnounce: []
   },
   connectionManager: {
-    minPeers: 25
+    minConnections: 25
   },
   transportManager: {
     faultTolerance: FaultTolerance.FATAL_ALL
diff --git a/src/connection-manager/index.js b/src/connection-manager/index.js
index e0e64e7cdd..969877d8fd 100644
--- a/src/connection-manager/index.js
+++ b/src/connection-manager/index.js
@@ -1,9 +1,12 @@
 'use strict'
 
+const debug = require('debug')
+const log = debug('libp2p:connection-manager')
+log.error = debug('libp2p:connection-manager:error')
+
 const errcode = require('err-code')
 const mergeOptions = require('merge-options')
 const LatencyMonitor = require('./latency-monitor')
-const debug = require('debug')('libp2p:connection-manager')
 const retimer = require('retimer')
 
 const { EventEmitter } = require('events')
@@ -22,6 +25,7 @@ const defaultOptions = {
   maxReceivedData: Infinity,
   maxEventLoopDelay: Infinity,
   pollInterval: 2000,
+  autoDialInterval: 10000,
   movingAverageInterval: 60000,
   defaultPeerValue: 1
 }
@@ -45,6 +49,8 @@ class ConnectionManager extends EventEmitter {
    * @param {Number} options.pollInterval How often, in milliseconds, metrics and latency should be checked. Default=2000
    * @param {Number} options.movingAverageInterval How often, in milliseconds, to compute averages. Default=60000
    * @param {Number} options.defaultPeerValue The value of the peer. Default=1
+   * @param {boolean} options.autoDial Should preemptively guarantee connections are above the low watermark. Default=true
+   * @param {Number} options.autoDialInterval How often, in milliseconds, it should preemptively guarantee connections are above the low watermark. Default=10000
    */
   constructor (libp2p, options) {
     super()
@@ -57,7 +63,7 @@ class ConnectionManager extends EventEmitter {
       throw errcode(new Error('Connection Manager maxConnections must be greater than minConnections'), ERR_INVALID_PARAMETERS)
     }
 
-    debug('options: %j', this._options)
+    log('options: %j', this._options)
 
     this._libp2p = libp2p
 
@@ -73,8 +79,11 @@ class ConnectionManager extends EventEmitter {
      */
     this.connections = new Map()
 
+    this._started = false
     this._timer = null
+    this._autoDialTimeout = null
     this._checkMetrics = this._checkMetrics.bind(this)
+    this._autoDial = this._autoDial.bind(this)
   }
 
   /**
@@ -101,7 +110,11 @@ class ConnectionManager extends EventEmitter {
     })
     this._onLatencyMeasure = this._onLatencyMeasure.bind(this)
     this._latencyMonitor.on('data', this._onLatencyMeasure)
-    debug('started')
+
+    this._started = true
+    log('started')
+
+    this._options.autoDial && this._autoDial()
   }
 
   /**
@@ -109,11 +122,13 @@ class ConnectionManager extends EventEmitter {
    * @async
    */
   async stop () {
+    this._autoDialTimeout && this._autoDialTimeout.clear()
     this._timer && this._timer.clear()
     this._latencyMonitor && this._latencyMonitor.removeListener('data', this._onLatencyMeasure)
 
+    this._started = false
     await this._close()
-    debug('stopped')
+    log('stopped')
   }
 
   /**
@@ -157,12 +172,12 @@ class ConnectionManager extends EventEmitter {
   _checkMetrics () {
     const movingAverages = this._libp2p.metrics.global.movingAverages
     const received = movingAverages.dataReceived[this._options.movingAverageInterval].movingAverage()
-    this._checkLimit('maxReceivedData', received)
+    this._checkMaxLimit('maxReceivedData', received)
     const sent = movingAverages.dataSent[this._options.movingAverageInterval].movingAverage()
-    this._checkLimit('maxSentData', sent)
+    this._checkMaxLimit('maxSentData', sent)
     const total = received + sent
-    this._checkLimit('maxData', total)
-    debug('metrics update', total)
+    this._checkMaxLimit('maxData', total)
+    log('metrics update', total)
     this._timer.reschedule(this._options.pollInterval)
   }
 
@@ -188,7 +203,7 @@ class ConnectionManager extends EventEmitter {
       this._peerValues.set(peerIdStr, this._options.defaultPeerValue)
     }
 
-    this._checkLimit('maxConnections', this.size)
+    this._checkMaxLimit('maxConnections', this.size)
   }
 
   /**
@@ -248,7 +263,7 @@ class ConnectionManager extends EventEmitter {
    * @param {*} summary The LatencyMonitor summary
    */
   _onLatencyMeasure (summary) {
-    this._checkLimit('maxEventLoopDelay', summary.avgMs)
+    this._checkMaxLimit('maxEventLoopDelay', summary.avgMs)
   }
 
   /**
@@ -257,15 +272,69 @@ class ConnectionManager extends EventEmitter {
    * @param {string} name The name of the field to check limits for
    * @param {number} value The current value of the field
    */
-  _checkLimit (name, value) {
+  _checkMaxLimit (name, value) {
     const limit = this._options[name]
-    debug('checking limit of %s. current value: %d of %d', name, value, limit)
+    log('checking limit of %s. current value: %d of %d', name, value, limit)
     if (value > limit) {
-      debug('%s: limit exceeded: %s, %d', this._peerId, name, value)
+      log('%s: limit exceeded: %s, %d', this._peerId, name, value)
       this._maybeDisconnectOne()
     }
   }
 
+  /**
+   * Proactively tries to connect to known peers stored in the PeerStore.
+   * It will keep the number of connections below the upper limit and sort
+   * the peers to connect based on wether we know their keys and protocols.
+   * @async
+   * @private
+   */
+  async _autoDial () {
+    const minConnections = this._options.minConnections
+
+    const recursiveTimeoutTrigger = () => {
+      if (this._autoDialTimeout) {
+        this._autoDialTimeout.reschedule(this._options.autoDialInterval)
+      } else {
+        this._autoDialTimeout = retimer(this._autoDial, this._options.autoDialInterval)
+      }
+    }
+
+    // Already has enough connections
+    if (this.size >= minConnections) {
+      recursiveTimeoutTrigger()
+      return
+    }
+
+    // Sort peers on wether we know protocols of public keys for them
+    const peers = Array.from(this._libp2p.peerStore.peers.values())
+      .sort((a, b) => {
+        if (b.protocols && b.protocols.length && (!a.protocols || !a.protocols.length)) {
+          return 1
+        } else if (b.id.pubKey && !a.id.pubKey) {
+          return 1
+        }
+        return -1
+      })
+
+    for (let i = 0; i < peers.length && this.size < minConnections; i++) {
+      if (!this.get(peers[i].id)) {
+        log('connecting to a peerStore stored peer %s', peers[i].id.toB58String())
+        try {
+          await this._libp2p.dialer.connectToPeer(peers[i].id)
+
+          // Connection Manager was stopped
+          if (!this._started) {
+            return
+          }
+        } catch (err) {
+          log.error('could not connect to peerStore stored peer', err)
+        }
+      }
+    }
+
+    recursiveTimeoutTrigger()
+  }
+
   /**
    * If we have more connections than our maximum, close a connection
    * to the lowest valued peer.
@@ -274,12 +343,12 @@ class ConnectionManager extends EventEmitter {
   _maybeDisconnectOne () {
     if (this._options.minConnections < this.connections.size) {
       const peerValues = Array.from(this._peerValues).sort(byPeerValue)
-      debug('%s: sorted peer values: %j', this._peerId, peerValues)
+      log('%s: sorted peer values: %j', this._peerId, peerValues)
       const disconnectPeer = peerValues[0]
       if (disconnectPeer) {
         const peerId = disconnectPeer[0]
-        debug('%s: lowest value peer is %s', this._peerId, peerId)
-        debug('%s: closing a connection to %j', this._peerId, peerId)
+        log('%s: lowest value peer is %s', this._peerId, peerId)
+        log('%s: closing a connection to %j', this._peerId, peerId)
         for (const connections of this.connections.values()) {
           if (connections[0].remotePeer.toB58String() === peerId) {
             connections[0].close()
diff --git a/src/index.js b/src/index.js
index ad7a78281c..0fc2ce55d5 100644
--- a/src/index.js
+++ b/src/index.js
@@ -65,7 +65,13 @@ class Libp2p extends EventEmitter {
     this._discovery = new Map() // Discovery service instances/references
 
     // Create the Connection Manager
-    this.connectionManager = new ConnectionManager(this, this._options.connectionManager)
+    if (this._options.connectionManager.minPeers) { // Remove in 0.29
+      this._options.connectionManager.minConnections = this._options.connectionManager.minPeers
+    }
+    this.connectionManager = new ConnectionManager(this, {
+      autoDial: this._config.peerDiscovery.autoDial,
+      ...this._options.connectionManager
+    })
 
     // Create Metrics
     if (this._options.metrics.enabled) {
@@ -459,19 +465,19 @@ class Libp2p extends EventEmitter {
   async _onDidStart () {
     this._isStarted = true
 
-    this.connectionManager.start()
-
     this.peerStore.on('peer', peerId => {
       this.emit('peer:discovery', peerId)
       this._maybeConnect(peerId)
     })
 
-    // Once we start, emit and dial any peers we may have already discovered
+    // Once we start, emit any peers we may have already discovered
+    // TODO: this should be removed, as we already discovered these peers in the past
     for (const peer of this.peerStore.peers.values()) {
       this.emit('peer:discovery', peer.id)
-      this._maybeConnect(peer.id)
     }
 
+    this.connectionManager.start()
+
     // Peer discovery
     await this._setupPeerDiscovery()
   }
@@ -495,15 +501,15 @@ class Libp2p extends EventEmitter {
   /**
    * Will dial to the given `peerId` if the current number of
    * connected peers is less than the configured `ConnectionManager`
-   * minPeers.
+   * minConnections.
    * @private
    * @param {PeerId} peerId
    */
   async _maybeConnect (peerId) {
     // If auto dialing is on and we have no connection to the peer, check if we should dial
     if (this._config.peerDiscovery.autoDial === true && !this.connectionManager.get(peerId)) {
-      const minPeers = this._options.connectionManager.minPeers || 0
-      if (minPeers > this.connectionManager.size) {
+      const minConnections = this._options.connectionManager.minConnections || 0
+      if (minConnections > this.connectionManager.size) {
         log('connecting to discovered peer %s', peerId.toB58String())
         try {
           await this.dialer.connectToPeer(peerId)
diff --git a/test/connection-manager/index.node.js b/test/connection-manager/index.node.js
index 3a3d000297..efa09d7cc7 100644
--- a/test/connection-manager/index.node.js
+++ b/test/connection-manager/index.node.js
@@ -7,6 +7,9 @@ chai.use(require('chai-as-promised'))
 const { expect } = chai
 const sinon = require('sinon')
 
+const delay = require('delay')
+const pWaitFor = require('p-wait-for')
+
 const peerUtils = require('../utils/creators/peer')
 const mockConnection = require('../utils/mockConnection')
 const baseOptions = require('../utils/base-options.browser')
@@ -112,4 +115,148 @@ describe('libp2p.connections', () => {
     await libp2p.stop()
     await remoteLibp2p.stop()
   })
+
+  describe('proactive connections', () => {
+    let nodes = []
+
+    beforeEach(async () => {
+      nodes = await peerUtils.createPeer({
+        number: 2,
+        config: {
+          addresses: {
+            listen: ['/ip4/127.0.0.1/tcp/0/ws']
+          }
+        }
+      })
+    })
+
+    afterEach(async () => {
+      await Promise.all(nodes.map((node) => node.stop()))
+      sinon.reset()
+    })
+
+    it('should connect to all the peers stored in the PeerStore, if their number is below minConnections', async () => {
+      const [libp2p] = await peerUtils.createPeer({
+        fixture: false,
+        started: false,
+        config: {
+          addresses: {
+            listen: ['/ip4/127.0.0.1/tcp/0/ws']
+          },
+          connectionManager: {
+            minConnections: 3
+          }
+        }
+      })
+
+      // Populate PeerStore before starting
+      libp2p.peerStore.addressBook.set(nodes[0].peerId, nodes[0].multiaddrs)
+      libp2p.peerStore.addressBook.set(nodes[1].peerId, nodes[1].multiaddrs)
+
+      await libp2p.start()
+
+      // Wait for peers to connect
+      await pWaitFor(() => libp2p.connectionManager.size === 2)
+
+      await libp2p.stop()
+    })
+
+    it('should connect to all the peers stored in the PeerStore until reaching the minConnections', async () => {
+      const minConnections = 1
+      const [libp2p] = await peerUtils.createPeer({
+        fixture: false,
+        started: false,
+        config: {
+          addresses: {
+            listen: ['/ip4/127.0.0.1/tcp/0/ws']
+          },
+          connectionManager: {
+            minConnections
+          }
+        }
+      })
+
+      // Populate PeerStore before starting
+      libp2p.peerStore.addressBook.set(nodes[0].peerId, nodes[0].multiaddrs)
+      libp2p.peerStore.addressBook.set(nodes[1].peerId, nodes[1].multiaddrs)
+
+      await libp2p.start()
+
+      // Wait for peer to connect
+      await pWaitFor(() => libp2p.connectionManager.size === minConnections)
+
+      // Wait more time to guarantee no other connection happened
+      await delay(200)
+      expect(libp2p.connectionManager.size).to.eql(minConnections)
+
+      await libp2p.stop()
+    })
+
+    it('should connect to all the peers stored in the PeerStore until reaching the minConnections sorted', async () => {
+      const minConnections = 1
+      const [libp2p] = await peerUtils.createPeer({
+        fixture: false,
+        started: false,
+        config: {
+          addresses: {
+            listen: ['/ip4/127.0.0.1/tcp/0/ws']
+          },
+          connectionManager: {
+            minConnections
+          }
+        }
+      })
+
+      // Populate PeerStore before starting
+      libp2p.peerStore.addressBook.set(nodes[0].peerId, nodes[0].multiaddrs)
+      libp2p.peerStore.addressBook.set(nodes[1].peerId, nodes[1].multiaddrs)
+      libp2p.peerStore.protoBook.set(nodes[1].peerId, ['/protocol-min-conns'])
+
+      await libp2p.start()
+
+      // Wait for peer to connect
+      await pWaitFor(() => libp2p.connectionManager.size === minConnections)
+
+      // Should have connected to the peer with protocols
+      expect(libp2p.connectionManager.get(nodes[0].peerId)).to.not.exist()
+      expect(libp2p.connectionManager.get(nodes[1].peerId)).to.exist()
+
+      await libp2p.stop()
+    })
+
+    it('should connect to peers in the PeerStore when a peer disconnected', async () => {
+      const minConnections = 1
+      const autoDialInterval = 1000
+
+      const [libp2p] = await peerUtils.createPeer({
+        fixture: false,
+        config: {
+          addresses: {
+            listen: ['/ip4/127.0.0.1/tcp/0/ws']
+          },
+          connectionManager: {
+            minConnections,
+            autoDialInterval
+          }
+        }
+      })
+
+      // Populate PeerStore after starting (discovery)
+      libp2p.peerStore.addressBook.set(nodes[0].peerId, nodes[0].multiaddrs)
+
+      // Wait for peer to connect
+      const conn = await libp2p.dial(nodes[0].peerId)
+      expect(libp2p.connectionManager.get(nodes[0].peerId)).to.exist()
+
+      await conn.close()
+      // Closed
+      await pWaitFor(() => libp2p.connectionManager.size === 0)
+      // Connected
+      await pWaitFor(() => libp2p.connectionManager.size === 1)
+
+      expect(libp2p.connectionManager.get(nodes[0].peerId)).to.exist()
+
+      await libp2p.stop()
+    })
+  })
 })
diff --git a/test/connection-manager/index.spec.js b/test/connection-manager/index.spec.js
index 8ffb0ee19c..caf6becb8a 100644
--- a/test/connection-manager/index.spec.js
+++ b/test/connection-manager/index.spec.js
@@ -58,7 +58,8 @@ describe('Connection Manager', () => {
       config: {
         modules: baseOptions.modules,
         connectionManager: {
-          maxConnections: max
+          maxConnections: max,
+          minConnections: 2
         }
       },
       started: false
@@ -96,7 +97,8 @@ describe('Connection Manager', () => {
       config: {
         modules: baseOptions.modules,
         connectionManager: {
-          maxConnections: max
+          maxConnections: max,
+          minConnections: 0
         }
       },
       started: false
diff --git a/test/peer-discovery/index.spec.js b/test/peer-discovery/index.spec.js
index b6e355eed1..fcada30ca9 100644
--- a/test/peer-discovery/index.spec.js
+++ b/test/peer-discovery/index.spec.js
@@ -31,10 +31,13 @@ describe('peer discovery', () => {
       sinon.reset()
     })
 
-    it('should dial know peers on startup', async () => {
+    it('should dial know peers on startup below the minConnections watermark', async () => {
       libp2p = new Libp2p({
         ...baseOptions,
-        peerId
+        peerId,
+        connectionManager: {
+          minConnections: 2
+        }
       })
 
       libp2p.peerStore.addressBook.set(remotePeerId, [multiaddr('/ip4/165.1.1.1/tcp/80')])