DIVIDEND REINVESTMENT PLAN PROSPECTUS SUPPLEMENT

INTRODUCTION

Pitney Bowes Inc. (“Pitney Bowes” or the “Company”) is pleased to offer existing stockholders the opportunity to participate in its Dividend Reinvestment Plan (the “Plan”). This Prospectus Supplement (the “Prospectus Supplement”) relates to an offering of 1,400,000 shares of Pitney Bowes common stock offered for purchase under the Plan. The Plan is available for existing stockholders to increase their holdings of Pitney Bowes common stock. Unless we have indicated otherwise, references in this Prospectus Supplement to “we,” “us” and “our” or similar terms refer to Pitney Bowes Inc., a Delaware company, and its consolidated subsidiaries.

The Plan allows participants to:

Shares purchased under the Plan may be newly issued Shares or Shares purchased for participants in the open market. The purchase price for newly issued Shares will be the closing

price of Shares on the New York Stock Exchange composite transactions tape on the date of purchase. The purchase price for Shares purchased in the open market will be the weighted average price paid for all Shares purchased by the Administrator (as defined below) for the Plan through a registered broker-dealer on the date of purchase. Shares purchased under the Plan will be recorded in uncertificated form in a participant’s account (a “Dividend Reinvestment Account”) by the Administrator.

Pitney Bowes is a global technology company offering innovative products and solutions that helps its clients navigate the complex world of commerce. The principal executive offices of the Company are located at 3001 Summer Street, Stamford, CT 06926.

Please read this Prospectus Supplement carefully and retain it and any future investment statements for future reference. If you have any questions regarding the Plan, please call toll free at (800) 648-8170 or (720) 414-6868. Customer service representatives are available between the hours of 9:00 a.m. and 5:00 p.m., Eastern Time, Monday through Friday.

The description of the Plan contained in this Prospectus Supplement supplements, and to the extent it is inconsistent with, supersedes the description of the Plan in the accompanying prospectus. This document supersedes all other prior prospectuses with respect to the Plan.

INFORMATION ABOUT THE COMPANY

Pitney Bowes Inc. was incorporated in the state of Delaware in 1920. We are a global technology company offering innovative products and solutions that help our clients navigate the complex world of commerce. We offer customer information management, location intelligence and customer engagement products and solutions to help our clients market to their customers, and shipping and

mailing, and cross border ecommerce products and solutions that enable the sending of parcels and packages across the globe. More than 1.5 million clients around the world rely on our products, solutions and services. Our world headquarters are located at 3001 Summer Street, Stamford, CT 06926. Our telephone number is (203) 356-5000.

We operate both inside and outside the United States. Our business is organized around three distinct sets of solutions -- Small and Medium Business (SMB) Solutions, Enterprise Business Solutions and Digital Commerce Solutions (DCS). The principal products and services of each of our reporting segments are as follows:

Small and Medium Business Solutions

We are a global leader in providing a full range of equipment, software, supplies and services that enable our clients to efficiently create physical and digital mail and evidence postage for the sending of mail, flats and parcels. We segment the SMB Solutions group between our North America operations, comprising the U.S. and Canadian businesses, and our International operations, comprising all other SMB businesses globally. We are a leading provider of mailing systems globally with about 900,000 meters installed in our North America operations and over 300,000 meters installed elsewhere. This business is characterized by a high level of recurring revenue driven by rental, lease and loan arrangements, contract support services and supplies sales.

Enterprise Business Solutions

Our Enterprise Business Solutions group includes equipment and services that enable large enterprises to process inbound and outbound mail. The Enterprise Business

Solutions group includes our Production Mail operations and Presort Services operations.

Production Mail

Our product and service offerings enable clients to integrate all areas of print and mail into an end-to-end production environment from message creation to dispatch while realizing cost savings on postage. The core products within this segment include high-speed, high-volume inserting equipment, customized sortation products for mail and parcels and high-speed digital color printing systems that create high-value, relevant and timely communications targeted to our clients’ customers. Beginning in 2016, we will offer new services and technical innovations including cloud connectivity for machines.

Presort Services

We are a national outsource provider of mail presort services for first-class, standard-class and flat mail in the U.S. and a workshare partner of the United States Postal Service (USPS). Our Presort Services network and fully-customized proprietary technology provides our clients with end-to-end solutions from pick up at their location to delivery into the postal system network. We process approximately 15 billion pieces of mail annually and are able to expedite mail delivery and optimize postage savings for our clients.

Digital Commerce Solutions

Within the Digital Commerce Solutions group, we provide a broad range of solutions, including customer information management, location intelligence and customer engagement software and shipping management and cross border ecommerce solutions for businesses of all sizes. These solutions are primarily delivered as traditional software licenses, enterprise platforms,

software-as-a-service (SaaS) and on-demand applications. Our Digital Commerce Solutions group includes Software Solutions and Global Ecommerce.

Software Solutions

Customer information management solutions help businesses harness and deliver a deep and broad understanding of their customers and their context, such as location, relationships, propensity, sentiment and influence. The trusted data and associated insights allow our clients to deliver a personalized customer experience across multiple channels, manage risk and compliance, and improve sales, marketing and service effectiveness. We are one of the market leaders in the data quality segment. Large corporations and government agencies rely on our products in complex, high-volume, transactional environments to support their business processes.

Location intelligence solutions enable our clients to organize and understand the complex relationships between location, geographic and other forms of data to drive business decisions and customer experiences. Our location intelligence solutions use predictive analytics, location, geographic and socio-demographic characteristics, which enable our clients to harness the power of location to better serve their customers, solve business problems, deliver location-based services and ultimately drive business growth.

Customer engagement solutions provide clients with insight and understanding into customer behavior and interactions across the entire customer lifecycle, enabling them to orchestrate impactful, relevant and timely physical and digital interactions. When coupled with our

inserting, sortation and digital print products, we are able to provide clients an all-inclusive solution that enables them to create, print and distribute wide-spread targeted customer communications. Our customer engagement solutions enable our clients to create connected experiences that positively influence future consumer behavior and generate business growth.

Global Ecommerce

Global Ecommerce includes our cross-border ecommerce solutions and shipping management solutions. Our cross-border ecommerce technology and services platforms enable retailers to transact with consumers globally. With our proprietary technology, we are able to manage all aspects of the international shopping and shipping experience, including multi-currency pricing, payment processing, fraud management, calculation of fully landed costs by quoting duty, taxes and shipping at checkout, compliance with product restrictions, export complexities and documentation requirements for customs clearance and brokerage and global logistics services. Our cross-border ecommerce software platforms are currently utilized by over 250 direct merchants as well as a major online marketplace enabling millions of parcels to be shipped to over 200 countries and territories worldwide. In 2015, we expanded our cross-border ecommerce capabilities through the acquisition of Borderfree, Inc.

Shipping management solutions enable clients to reduce transportation and logistics costs, select the best carrier based on need and cost, improve delivery times and track packages in real-time. We also offer scalable global logistics management systems that can be integrated into mail centers for the office and retail markets, as well as desktop and production shipping environments.

FORWARD-LOOKING STATEMENTS

This prospectus supplement contains and incorporates by reference statements that are forward-looking. We caution readers that any for-ward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended and Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), in this prospectus supplement may change based on various factors. These forward-looking statements are based on current expectations and assumptions that are subject to risks and uncertainties and actual results could differ materially. Words such as “estimate”, “target”, “project”, “plan”, “believe”, “expect”, “anticipate”, “intend”, and similar expressions may identify such forward-looking statements. We undertake no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise. Factors which could cause future financial performance to differ materially from the expectations as expressed in any forward-looking statement made by or on our behalf include, without limitation:

RISK FACTORS

An investment in our common stock involves risks. You should carefully consider the following risk factors, as well as the information contained or incorporated by reference in this prospectus supplement, including the information under the heading “Risk Factors” in our Annual Report on Form 10-K for the year ended December 31, 2015, before making an investment in our securities.

Risks Relating to the Plan

You will not be able to predict or control the price at which Shares will be purchased under the Plan.

You will not know the price of the Shares you purchase under the Plan at the time you elect to have your dividends reinvested or to make an optional cash investment through the Administrator. The price of our Shares may fluctuate between the time you decide to purchase Shares under the Plan and the time of actual purchase. Furthermore, the purchase price, as determined under the Plan, may differ from the price you would have obtained if you had purchased Shares on the open market on the relevant investment date. As a result, you may purchase Shares at a price higher than the price you anticipated.

There is no price protection for your Shares under the Plan.

Your investment in Shares pursuant to the Plan will be exposed to changes in market conditions and changes in the market value of the Shares.

If you instruct the Administrator to sell Shares in your Dividend Reinvestment Account via a batch sale, you will not be able to direct the time or price at which the Shares are sold or select a broker or dealer through or from whom sales are to be made. The price of our common stock may decline between the time you decide to sell Shares and the time of actual sale.

Your ability to liquidate or otherwise dispose of Shares in your Dividend Reinvestment Account is subject to the terms of the Plan. You may not be able to sell the Shares in your Dividend Reinvestment Account in time to react to market conditions.

INFORMATION ABOUT THE PLAN

The following questions and answers explain and constitute the Plan.

The Plan is a convenient, low cost purchase plan available for existing stockholders to increase their holdings of Pitney Bowes common stock. Participants in the Plan may elect to have dividends automatically reinvested in Pitney Bowes common stock and to make optional cash investments through the Administrator. Participation in the Plan is entirely voluntary and we give no advice regarding your decision to join the Plan. A current stockholder can enroll in the Plan through the Internet at http://www.shareholder.broadridge.com/PBI by following the instructions provided. Enrollment forms may also be obtained from the

Administrator by calling (800) 648-8170 (inside U.S. and Canada) or 720-414-6868 (outside U.S. and Canada).

Advantages of participating in the Plan include the ability to:

Potential disadvantages of participating in the Plan, which you should consider before deciding whether to participate in the Plan, include the following:

These and additional considerations are discussed below in this Prospectus Supplement.

Broadridge Corporate Issuer Solutions, Inc. (the “Administrator” or “Broadridge”) is the Administrator of the Plan through a registered broker-dealer. Broadridge will direct the purchase of Shares acquired under the Plan, hold such Shares, keep records and perform other functions related to the Plan.

Participants may contact Broadridge by:

For overnight delivery services: Broadridge Corporate Issuer Solutions, Inc., 1155 Long Island Avenue Attn: IWS Edgewood, NY 11717

The Administrator administers the Plan by acquiring Newly Issued Shares (as defined below), or purchasing Shares in the open market through a registered broker-dealer if Newly Issued Shares are not available, keeping records, sending statements of account to participants, holding Shares of all participants together in its name or in the name of its nominee and performing other duties related to the Plan.

The term “Newly Issued Shares” refers to original issue Shares and Shares held by the Company in treasury. When Newly Issued Shares are purchased from the Company, the Company will receive new equity capital funds available for general corporate purposes.

The Administrator also acts as dividend disbursing and transfer agent for the Shares.

Stockholders who have at least one Share registered in their name (“Eligible Stockholders”) are eligible to participate. Stockholders residing outside the U.S. should determine whether they are subject to any governmental regulation in their country of residence that would prohibit their participation. If Shares are registered in a name other than the stockholder (e.g., in the name of a broker or bank nominee) and the stockholder wants to participate, the stockholder must either become a stockholder of record by having a part or all of their Shares transferred to their name, or, if their broker or fiduciary agrees, authorize their broker or fiduciary to participate for them.

Only holders of common stock may participate in the Plan. Holders of $2.12 Convertible Cumulative Preference Stock or 4% Convertible Cumulative Preferred Stock or

other securities of the Company may not participate in the Plan.

However, in the future, the Company from time to time, in its sole discretion, may permit holders of certain other securities issued by the Company to participate in the Plan on such terms and conditions as the Company may from time to time establish for such purposes. To the extent the Company permits such participation by such holders, wherever the provisions of the Plan refer to holders of common stock of the Company or Shares such references will be deemed to include holders of such other securities, as the context requires.

An Eligible Stockholder may enroll in the Plan by signing an enrollment form and returning it to the Administrator or by enrolling on the Internet at http://www.shareholder.broadridge.com/PBI Enrollment forms and copies of the prospectus for the Plan may be obtained at any time by contacting Broadridge as discussed in Question 3.

An Eligible Stockholder may join the Plan at any time. If an enrollment form or online enrollment specifying reinvestment of dividends is received by the Administrator at least 5 days prior to the record date established for a particular dividend, reinvestment will commence with that dividend. If the enrollment form or online enrollment is received after the timeline mentioned above, then the reinvestment of dividends will begin with the following dividend payment.

Participants pay no fees, commissions or expenses for purchases made under the Plan. The Company pays all costs of administration of the Plan. Please see Question 24 for information concerning fees related to sales of Shares purchased through the Plan.

Participants in the Plan may elect to reinvest all, part or none of their dividends on their Shares in additional Shares:

sent to the participant by check or through direct deposit to his or her U.S. bank account. A participant can make cash deposits for the purchase of additional Shares without reinvesting dividends on Shares registered in his or her name.

Broadridge will continue to reinvest a participant’s dividends as indicated on his or her enrollment form until the participant specifies otherwise. A participant may change a dividend option at any time by contacting Broadridge as discussed in Question 3.

Record dates for determining the record holders of common stock entitled to receive cash dividends for common stock will be designated by the board of directors of Pitney Bowes. Historically, the record dates have typically been in the months of February, May, August and November. Broadridge must receive an enrollment form or online enrollment specifying reinvestment of dividends at least 5 days in advance of the record date for any given dividend payment date in order for the enrollment to be effective for that dividend. If a participant’s enrollment form or online enrollment is received after the timeframe mentioned above, then the request will not be effective until the next dividend record date. Dividend record dates may vary from time to time, and may be designated in months other than those listed above.

A participant may make an optional cash deposit with the Administrator (an “Optional Cash Deposit”) by mailing a check accompanied

by the tear-off portion, properly executed, of the account statement sent to participants. All checks must be payable in U.S. dollars and drawn on a U.S. bank, payable to Broadridge. Do not send cash or traveler’s checks.

Shares purchased with Optional Cash Deposits will be held by the Administrator and credited to the participant’s Dividend Reinvestment Account under the Plan. Future dividends on these Shares will be used to purchase additional Shares as designated by the participant.

Automatic Bank Draft – A participant may also pre-authorize Broadridge to deduct a set amount from a U.S. checking, savings or credit union account. To initiate the bank draft, the participant must complete and sign the Authorization for Monthly Investments – Optional section of the Enrollment Form, and return it to Broadridge with a voided check for the bank account from which funds are to be drafted. Automatic bank drafts will be initiated as promptly as practicable. A participant may also authorize an online bank debit by logging into their online account and selecting “Plan Options”.

As an added security measure, Broadridge may apply a five business day hold period to the initial association of banking account information to a participant’s investor account as well as changes made to established direct deposit or direct debit instructions. This hold period is intended to help prevent unauthorized transactions.

After the automatic bank draft is established, recurring investment funds will be drawn on the 8th of each month or if that date falls on a non-business day, the next business day. A participant can also establish a onetime debit instance to be drawn from an account. A participant should allow up to 4 weeks for the first automatic bank draft to be initiated. In order to terminate a bank draft, a participant must

notify Broadridge in writing at least ten (10) business days prior to the next automatic bank draft date in order for the termination to be effective by that date.

Optional Cash Deposits may not be less than $100 per deposit. They may not total more than $3,000 per quarter. The same amount of money need not be sent each time. There is no obligation to make an Optional Cash Deposit.

The investment date for dividend reinvestment is the dividend payment date. If the dividend payment date does not fall on a trading day, the investment date will be the next trading day. Historically, the payment of dividends for Pitney Bowes common stock has typically taken place on the 12^th day of March, June, September and December.

For Optional Cash Deposits, the investment date will typically be the 12th day of each month or the next trading day if the 12th day is not a trading day. No interest will be paid by the Company or the Administrator on Optional Cash Deposits.

For an Optional Cash Deposit to be invested on the next investment date, the funds must be received no later than two business days prior to the investment date.

The Company remits to the Administrator the aggregate amount of dividends which all participants have elected for reinvestment. The Administrator uses dividends and Optional

Cash Deposits to acquire Newly Issued Shares from the Company, if the Company is then making Newly Issued Shares available, for the accounts of participants. If the Company is not then making Newly Issued Shares available for purchase under the Plan, the Administrator will through a registered broker-dealer purchase Shares in the open market or in negotiated transactions for the accounts of the participants. The Administrator will acquire Shares with cash dividends promptly after their receipt and with Optional Cash Deposits on the dates described under Question 13.

No. Interest will not be paid on funds held prior to investment.

The purchase price for Shares (“Share Purchase Price”) will be calculated as follows:

All Shares purchased under the Plan on the open market will be acquired as soon as practicable on or after the dividend payment date and all such purchases will be completed no later than 30 days from that date for the reinvestment of dividends and 35 days from that date for Optional Cash Deposits, except where

completion at a later date is necessary or advisable under any applicable federal securities laws. Neither the Company nor the participant shall have any authority or power to direct the time or price at which Shares may be purchased, or the selection of a broker or dealer through or from whom purchases are to be made.

The Share Purchase Price will be calculated in the same way whether Shares are purchased with reinvested dividends or Optional Cash Deposits.

Yes. If any dividend or Optional Cash Deposit payment is not sufficient to purchase a whole share of Pitney Bowes common stock, a fractional Share will be credited to a participant’s Dividend Reinvestment Account in book entry form. All fractional Shares are computed to six decimal places.

In the event that any participant’s check for a cash contribution is returned unpaid for any reason, the Administrator will consider the request for investment of such funds null and void. The Administrator shall immediately remove from the participant’s Dividend Reinvestment Account those Shares, if any, purchased upon the prior credit of such funds. The Administrator shall thereupon be entitled to sell Shares through a registered broker-dealer to satisfy any uncollected amount plus any applicable fees. If the net proceeds of the sale of such Shares are insufficient to satisfy the balance of such uncollected amounts, the Administrator, through a registered broker-dealer, shall be entitled to sell such additional Shares from the participant’s Dividend Reinvestment Account as may be necessary to satisfy the uncollected balance.

Certificates for Shares purchased under the Plan will not be issued. Shares will be issued and held in book-entry form by the Administrator. Certificates for fractional Shares will not be issued.

When shares that were held in a Dividend Reinvestment Account are issued, they will be registered in the name in which the Dividend Reinvestment Account has been maintained.

Since the Administrator is the holder of record for all Shares credited to Dividend Reinvestment Accounts, a participant may not pledge or assign these Shares and any such purported pledge or assignment will be void. Such Shares when withdrawn from a Dividend Reinvestment Account may be so pledged, and the dividends payable on them may continue to be eligible for reinvestment under this Plan.

Yes. A participant may increase the number of Shares held in his or her Dividend Reinvestment Account by depositing with the Administrator for safekeeping certificates representing certificated Shares with the Administrator. The advantages of holding Shares in this manner are protection against certificate loss, theft and damage. Such certificates must be registered in the participant’s name and must be sent to the Administrator at the address provided in Question 3 by registered or certified mail, with return receipt requested, or some other form of traceable mail. Certificate(s) should not be

signed nor should the assignment section be completed.

When submitting stock certificate(s) for deposit into a Dividend Reinvestment Account, be sure to include a written request that the Shares be added to the Dividend Reinvestment Account.

Participation in the Plan may be terminated at any time by contacting the Administrator as shown in Question 3 before the next dividend record date. If, after the dividend record date, the Administrator receives a request to terminate participation, the Administrator may either pay the dividend in cash or reinvest under the Plan on behalf of the participant. If the Shares are reinvested, the Administrator may sell the Shares purchased through a registered broker-dealer and send the proceeds to the participant less any applicable fees. Subsequent dividends will be paid in the form of a check and mailed or electronically deposited to the bank account of choice if such information is on file with the Administrator.

Participation in the Plan may also be terminated if the Administrator receives instruction to terminate and written notice of the death or adjudicated incompetency of a participant from the legal representative that has been appointed accompanied by legal documentation demonstrating to the satisfaction of the Administrator the legal representative’s right to order such termination and/or re-register the share holdings. In the event these materials are received by the Administrator later than the dividend record date, Shares will be purchased for the participant with the related cash dividend. Once terminated, subsequent dividends will be paid in the form of a check and mailed or electronically deposited to the

bank account of choice if such information is on file with the Administrator.

If a participant wishes to discontinue having all or partial dividends reinvested, the participant can request the Administrator to cause the participant’s account to receive cash dividends. Shares will remain in the participant’s existing account; however future dividends will be paid to the participant in cash.

If a participant chooses to terminate the participant’s account with the Administrator, the participant will need to contact the Administrator and instruct it as to how the participant wants to handle the share balance. Only whole Shares can be transferred to a broker or issued to a participant in book entry form. Any fractional Share held in a participant’s account will be sold as shown in Question 34. The current market price is used to calculate the price of a participant’s fractional Share.

At any time, a participant may contact the Administrator through one of the methods shown in Question 3, to request that some or (upon termination) all of the Shares in the participant’s Dividend Reinvestment Account be sold. Sales usually take place within 5 business days of the day that a sale request is received by the Administrator.

The participant will receive the actual proceeds from the sale of Shares, less a service fee of $15.00 and a per share fee of $0.10 for

batch sales and any other costs of sale, except that when the Administrator is handling sales for two or more participants each participant will receive the weighted average sales price from all Shares sold by the broker-dealer engaged by the Administrator, less applicable fees. Per share fees include any applicable brokerage commission charged by the broker-dealer selected by the Administrator that the Administrator is required to pay. All sales requests having an anticipated market value of $50,000 or more must be submitted in written form or executed via the shareholder portal. Participants may also sell Shares through a broker of their choosing, by requesting a book statement representing their Shares and depositing those Shares via DRS with their broker. Participants may instruct the Administrator to sell Shares under the Plan through a batch order, market order, day limit order, good-’til-date/canceled limit order or stop order; however, all sales options may not be available at all times and options are pending availability at the administrator. These options may require additional processing fees as applicable.

Batch Order (online, mail, phone) – The Administrator will combine each request to sell through the Plan with other participant sale requests for a batch order. Shares are then periodically submitted in bulk to a broker for sale on the open market. Shares will be sold no later than five business days from receipt of the sales request (except where deferral is necessary under state or federal regulations). Bulk sales may be executed in multiple transactions and over more than one day depending on the number of Shares being sold and current trading volumes. Once entered, a batch order request cannot be canceled.

Market Order (online or telephone) – A participant’s request to sell Shares in a market order will be executed at the prevailing market price when the trade is executed. If such an order is placed during market hours, the Administrator will promptly submit the Shares to a broker for sale

on the open market. Requests to sell Shares in a market order submitted near the close of the market may be executed on the next trading day, along with other requests received after market close.

Day Limit Order (online or telephone) – A participant’s request to sell Shares in a day limit order will be promptly submitted by the Administrator to a broker. The broker will execute as a Market Order when and if the stock reaches or exceeds the specified price on the day the order was placed (for orders placed outside of market hours, the next trading day). The order is automatically canceled if the price is not met by the end of that trading day.

Good-’Til-Date/Canceled (GTD/GTC) Limit Order (online or telephone) – A GTD/GTC Limit Order request will be promptly submitted by the Administrator to a broker. The broker will execute the request as a Market Order when and if the stock reaches or exceeds the specified price at any time while the order remains open (up to the date requested or 90 days in the case of a GTC Limit Order). Depending on the number of Shares being sold and trading volumes, sales may be executed in multiple transactions and may be traded on more than one day. The order or any unexecuted portion will be automatically canceled if the price is not met by the end of the order period. The order may also be canceled by the applicable stock exchange or the participant.

Stop Order (online or telephone) – The Administrator will promptly submit a participant’s request to sell Shares in a stop order to a broker. A sale will be executed if and when the stock reaches a specified price, at which time the stop order becomes a market order and the sale will be at the prevailing market price when the trade is executed. The price specified in the order must be below the current market price. Alternatively, a participant may choose to sell Shares in a Dividend Reinvestment Account through a broker of the participant’s choice, in

which case the participant should contact the participant’s broker about transferring Shares from the participant’s Dividend Reinvestment Account to the participant’s brokerage account.

Yes, participants may make gifts or transfers of Shares at no charge. Participants may contact Broadridge as indicated under Question 3 for transfer instructions. Transfers may be made to new or existing Pitney Bowes stockholders.

Yes, the Administrator will transfer Shares from the Plan via book entry/DRS to a participant after a withdrawal request has been received. However, participant accounts with less than one full Share will be terminated. See Question 3 for information regarding contacting the Administrator.

A participant may change investment options at any time by completing a new enrollment form or online enrollment or by contacting the Administrator as described in Question 3.

Yes. As the record holder for the Shares held in each participant’s Dividend Reinvestment Account under the Plan, the Administrator will receive dividends for all such Shares held on the dividend record date and will

credit these dividends to participants’ Dividend Reinvestment Accounts on the basis of full and fractional Shares held in these Dividend Reinvestment Accounts. To the extent that a participant has so elected, the Administrator will reinvest such dividends in additional Shares, in accordance with a participant’s reinvestment option.

A participant may elect to have any cash dividends not reinvested paid by electronic funds transfer to a designated U.S. bank account. To do this, an Authorization for Electronic Direct Deposit Form must be completed and returned to the Administrator along with a copy of a voided blank check or savings account deposit slip. This form must be specifically requested from the Administrator.

The Administrator must receive an Authorization for Electronic Direct Deposit Form at least seven business days before the dividend record date for the form to be effective for that dividend. Forms received after that date will not become effective until the following dividend. A new Authorization for Electronic Direct Deposit Form must be completed if a participant transfers ownership of Shares or establishes a new account with the Administrator, the designated U.S. bank account has been closed or changed, or if the designated bank has assigned a new account number. The participant must complete proper forms in order to receive dividend payments other than by check. The participant can contact the Administrator to discontinue this option.

As an added security measure, Broadridge may apply a five business day hold period to the initial association of banking account information

to a participant’s investor account as well as changes made to established direct deposit or direct debit instructions. This hold period is intended to help prevent unauthorized transactions.

The Administrator will mail each participant (except those whose Shares are held in street name) a statement confirming purchases of Shares as soon as practicable after the purchases, showing funds invested, prices of Shares purchased and the total Shares held by the Administrator with respect to that participant. The statement will also reflect the cost basis of any Shares acquired after January 1, 2011 and should be retained for tax purposes. Participants will receive copies of the Company’s annual report and other reports to stockholders, proxy materials and dividend income information for tax purposes.

Participants may also view year-to-date transaction activity in their Dividend Reinvestment Account for the current year, as well as activity in prior years, by accessing their Dividend Re-investment Account online at http://www.shareholder.broadridge.com/PBI.

Any dividends in the form of Shares and any Shares resulting from a split of Shares distributed by the Company on Shares held by the participant will be credited to the participant’s Dividend Reinvestment Account with the appropriate number of Shares of common stock on the payment date and reflected in the statement described in Question 30.

Participants will receive one proxy card covering (i) the total number of whole Shares registered on the Company’s books in the participant’s name and (ii) the whole and/or fractional Shares credited to the participant’s Dividend Reinvestment Account. Participants may elect to receive in electronic format instead of by mail the Company’s proxy statement, proxy card and annual report and any other Company communications to stockholders through the Broadridge website. The Administrator will vote any Shares that it holds in a participant’s Dividend Reinvestment Account in accordance with the proxy returned by the participant to the Company. If a proxy card is returned properly signed, but without indicating instructions as to the manner Shares are to be voted with respect to any item thereon, the Shares covered will be voted in accordance with the recommendations of the Company’s management. If the proxy card is not returned, or if it is returned unexecuted or improperly executed, the Shares covered will not be voted unless the participant or the participant’s duly appointed representative votes in person at the meeting.

As an alternative to returning proxy cards, participants may also be able to vote by telephone or online by following the instructions in the proxy materials if these methods are available. Shares may also be voted in person at the stockholders’ meeting.

Yes. The Company may terminate or modify the Plan at any time in its sole discretion, including by changing the fees, charges and commissions that are applicable for transactions occurring under the Plan. Any termination or

modification of the Plan will not affect a participant’s rights as a stockholder, and any book-entry Shares owned will continue to be credited to the participant’s Dividend Reinvestment Account with the Administrator unless the participant specifically requests otherwise.

The Company or the Administrator may terminate a participant’s interest therein by mailing a written notice to the participant. In such event the Administrator will follow the procedures for termination as set forth in Questions 22 and 23.

From time to time, the Administrator may close a participant’s Dividend Reinvestment Account that contains less than one full Share, in which case any fractional Share will be sold. A check for the amount of the sale proceeds remaining after deduction of applicable fees, if any, will be mailed to the participant’s address of record.

Pitney Bowes and the Administrator may interpret and administer the Plan and resolve any questions or disputes as they believe appropriate or consistent with the Company’s goals in establishing the Plan. Neither the Company nor the Administrator shall be liable for any act done in good faith or for any good faith omission to act, including, without limitation, any claims or liability: (a) with respect to the prices at which Shares of stock are purchased or sold for a participant’s Dividend Reinvestment Account and the time when such purchases or sales are made; (b) for any fluctuation in the market value

after purchases or sale of Shares of stock; (c) with respect to the tax treatment of dividends or any transaction effected pursuant to the Plan; or (d) for continuation of a participant’s Plan participation until the Administrator receives written notice of the death of the participant accompanied by his or her estate’s request to discontinue participation.

Pitney Bowes and the Administrator provide no advice and make no recommendation with respect to a participant’s purchases and sales of Pitney Bowes stock. The decision to purchase or sell Pitney Bowes stock must be made by a participant based upon his or her own research and judgment.

In the event that the Company determines not to make Newly Issued Shares available for purchase pursuant to the Plan and applicable law or the closure of any securities market requires curtailment or suspension of open market purchases of Shares under the Plan, the Company and the Administrator will not be accountable for the inability to make purchases at such time, except that if Shares are not available for purchase for a period longer than 35 days, the Administrator will promptly mail to a participant a check payable to the participant in the amount of any unapplied funds in the participant’s Dividend Reinvestment Account.

Participants in the Plan are advised to consult their own tax advisors with respect to the tax consequences of participation in the Plan (including

U.S. federal, state, local and non-U.S. income and other tax laws and U.S. tax withholding laws) applicable to their particular situations.

Cash dividends reinvested under the Plan will be taxable for U.S. federal income tax purposes as having been received by you even though you have not actually received them in cash. The total amount of dividends paid to you during the year, whether or not they are reinvested, will be reported to you and the U.S. Internal Revenue Service (generally on IRS Form 1099-DIV or Form 1042-S, as applicable) shortly after the close of each year.

In the event that Broadridge, through a registered broker-dealer, purchases Shares with reinvested dividends in the open market rather than directly from Pitney Bowes, you must include in your gross income, as an additional dividend, your allocable share of per share fees (which include any applicable brokerage commissions Broadridge is required to pay) paid by Pitney Bowes. This amount will be also reported to you and the U.S. Internal Revenue Service in the manner described above. Your tax basis in these Shares will be the cost of the Shares plus your allocable share of per share fees paid by Pitney Bowes.

In the event that Broadridge acquires Shares with reinvested dividends directly from Pitney Bowes, your tax basis in these Shares will be the cost of the Shares.

You will not realize a gain or loss for U.S. federal income tax purposes upon a transfer of Shares to your account or the withdrawal of whole Shares from your account. You will, however, generally realize a gain or loss upon the receipt of cash for a fractional Share credited to your account and when Shares are sold in a sale, exchange or other taxable disposition. The amount of the gain or loss upon a sale of Shares will be the difference between the amount that you receive for the Shares sold and your tax basis

in the Shares. In order to determine the tax basis for Shares in your account, you should retain all account statements.

Plan participants who are non-resident aliens or non-U.S. corporations, partnerships or other entities generally are subject to a withholding tax (based upon the current applicable rate) on dividends paid on Shares held in the Plan. In addition, the U.S. Internal Revenue Service has announced that a withholding tax will apply to payments of gross proceeds from the sale or other disposition of Shares held in the Plan on or after January 1, 2019.

Dividends paid on Shares in accounts, and the proceeds of any sale of Shares, may be subject to the “backup withholding” provisions of the Internal Revenue Code. If you fail to furnish a properly completed Form W-9 or its equivalent or otherwise establish an exemption, then Broadridge must withhold the current applicable rate from the amount of dividends, the proceeds of the sale of a fractional Share and the proceeds of any sale of whole Shares.

The Company may from time to time designate a bank, broker or trust company as a successor to the Administrator under the Plan.

The laws of the State of New York govern the terms and conditions of the Plan and its operations.

WHERE YOU CAN FIND MORE INFORMATION

We file annual, quarterly and current reports, proxy statements and other information with the United States Securities and Exchange Commission (“SEC”).

You may read and copy any materials we file with the SEC at the SEC’s Public Reference Room at 100 F Street, N.E., Washington, DC 20549. You may obtain information on the operation of the Public Reference Room by calling the SEC at 1-800-SEC-0330. The SEC maintains an Internet site that contains reports, proxy and information statements, and other information regarding issuers that file electronically with the SEC at http:www.sec.gov.

We also post our SEC filings on our website at http://www.pb.com. Information contained on our website is not intended to be incorporated by reference in this Prospectus Supplement and you should not consider that information a part of this Prospectus Supplement. Our website address is included in this Prospectus Supplement as an inactive textual reference only.

INCORPORATION BY REFERENCE

The SEC allows us to “incorporate by reference” the information we file with it, which means we can disclose important information to you by referring you to other documents that contain that information. The information incorporated by reference is an important part of this Prospectus Supplement. Any information that we file with the SEC in the future and incorporate by reference will automatically update and supersede the information contained or incorporated by reference in this Prospectus Supplement. We incorporate by reference in this Prospectus Supplement the following documents filed by us with the SEC and any future filings made with the SEC by us under Sections 13(a),

13(c), 14 or 15(d) of the Exchange Act until we sell all of the securities, except as noted below:

All documents that we file with the SEC pursuant to Sections 13(a), 13(c), 14 or 15(d) of the Exchange Act from the date of this Prospectus Supplement and prior to the termination of all offerings made pursuant to this Prospectus Supplement also will be deemed to be incorporated herein by reference and will automatically update information in this Prospectus Supplement. Nothing in this Prospectus Supplement shall be deemed to incorporate information furnished but not filed with the SEC pursuant to Item 2.02 or Item 7.01 of Form 8-K.

Statements made in this Prospectus Supplement, in any prospectus supplement or in any document incorporated by reference in this Prospectus Supplement as to the contents of any contract or other document are not necessarily complete. In each instance we refer you to the copy of the contract or other document filed as an exhibit to the registration statement of which this Prospectus Supplement is a part or as an exhibit to the documents incorporated by reference.

Upon written or oral request, we will provide to each person, including any beneficial owner, to whom a prospectus is delivered, at no cost, a copy of any or all of the

information incorporated by reference in this Prospectus Supplement but not delivered with this Prospectus Supplement. You may request copies of this information from us by mail at the following address: Pitney Bowes Inc., 3001 Summer Street, Stamford, CT 06926, Attention: Investor Relations, or by telephone at the following telephone number: (203) 356-5000.

USE OF PROCEEDS

Proceeds from the Shares purchased from the Company will be available for general corporate purposes. The Company has no basis for estimating either the number of Shares that will ultimately be purchased from the Company, if any, under the Plan or the prices at which such Shares will be sold.

EXPERTS

The consolidated financial statements and management’s assessment of the effectiveness of internal control over financial reporting (which is included in Management’s Report on Internal Control Over Financial Reporting) incorporated in this Prospectus Supplement by reference to the Annual Report on Form 10-K for the year ended December 31, 2015 have been so incorporated in reliance on the report which contains an explanatory paragraph on the effectiveness of internal control over financial reporting due to the exclusion of certain elements of internal control over financial reporting of the Borderfree business the registrant acquired during 2015, of PricewaterhouseCoopers LLP, an independent registered public accounting firm, given on the authority of said firm as experts in auditing and accounting.