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Stockholders' Equity (Stock Compensation Plans) (Details)
12 Months Ended
Dec. 31, 2016
stock_based_compensation_plans
shares
Dec. 31, 2015
shares
Dec. 31, 2014
shares
Dec. 31, 2013
shares
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]        
Number of stock-based compensation plans | stock_based_compensation_plans 2      
Number of shares available for grant, annual increase (as a percent) 4.00%      
Restricted stock units outstanding (in shares) 839,477      
Stock Options [Member]        
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]        
Options outstanding (in shares) 759,719 778,388 665,210 357,991
Upland Software, Inc. 2010 Stock Plan [Member] | Stock Options [Member]        
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]        
Options outstanding (in shares) 294,502      
Upland Software, Inc. 2014 Stock Plan [Member] | Stock Options [Member]        
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]        
Options outstanding (in shares) 465,217      
Common stock shares reserved for issuance under the plan (in shares) 163,928